March 27, 2025 • 65 mins
Caleb Sherman is a comedian and has worked for almost a decade at the Empire Comedy Club in Portland, Maine, where he's become something of an accidental anthropologist of the open mic scene.
In this conversation, we explore the strange and beautiful world of amateur comedy, what it actually means to "find your voice," and why the grind of showing up night after night might not be such a grind after all.
From philosophy degrees to ass play, Caleb shares his journey and what he's learned from watching thousands of comedians try to make strangers laugh.
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Episode Transcript
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David (00:00):
Hello, welcome back to another very special episode of
Starting Stand Up at Maine withDavid Walton.
Today I, david Walton, amsitting down with Caleb Theodore
Sherman Very powerful name fora powerful man, a fascinating
figure in Portland Maine'scomedy scene.
(00:22):
Okay, caleb works and performsat the Empire Comedy Club.
It's a 140, 30-seat theaterthat gets huge names.
Caleb has been there since 2016.
He was born in 1992.
He was born to mental healthprofessionals in upstate New
(00:42):
York.
Caleb grew up in the Poconoswith an almost clinically
perfect upbringing His words,not mine.
He's been nurtured by veryconscientious parents who have
obviously screwed him up becausehe's in stand-up.
He studied philosophy incollege, which is a worthless
degree, as we all know, but hediscovered through a poetry
(01:03):
reading, his love forperformance.
These poetry open mics, but hefound himself more interested in
getting laughs than fingersnaps.
Since 2016, caleb has seen itall, and when I say that I, I
mean it quite literally.
I won't give away the number yet, but I believe Caleb has seen
(01:25):
more open mics than any otherhuman being on earth, and we had
a fascinating conversation.
I loved it.
One of the coolest things aboutdoing this is that I get to
meet people like Caleb, not knowhim, invite him to my home,
trust this man with long hairdown to his nipples who looks a
(01:47):
little bit dangerous in a goodway, but then turns out to be a
extremely soulful, kind,intelligent human being.
So what you're about to listento is two men getting to know
each other for the first time.
So, without further ado, pleaseenjoy this conversation that
(02:08):
dives deep into the craft ofcomedy, specifically open mics
and their value.
Here is my chat with CalebTheodore Sherman oh man, that's
(02:40):
rubbish.
Caleb (02:41):
That's rubbish.
Was born.
I was born in a bathtub at homeon purpose mama hippie uh, they
were my parents.
By the way, caleb has long hair.
David (02:54):
I would say nipple length , and he's got a good, some good
facial hair, but nicelymanicured.
He's not, doesn't look homeless.
Really.
You do have something going onwith your eyes which is
interesting.
Caleb (03:06):
Oh, vitiligo I have vitiligo facts that is that when
I was 14.
It's a harmless autoimmunedisorder where your body, your
immune system, destroys yourmelanocytes so you have patches
of your skin with no pigment.
Oh uh, michael jackson claimedto have had this disease but was
probably just like early on thekorean skincare trend of skin
lightening, sure, uh.
(03:26):
So we don't vitiligo people.
I I speak for us all when I sayI'm not sure that that was who
we would have picked for ourspokesperson, but that's who we
have as a point of recognition.
David (03:36):
Yeah, yeah, I've a bit on the hands and then on the eye
everywhere, oh everywhere.
Caleb (03:42):
That's exciting, ladies.
David (03:46):
No, no, but it looks just as a a first impression, it
looks like you have sixsunglasses that you're just like
rocking that's.
Caleb (03:54):
That's my favorite uh interpretation of what it might
be on on site, because I I dofear I get insecure, that people
will think that I'm tanninglike I'm just laying in a.
David (04:06):
Well, you just had a disastrous tanning bed session
where, like this is a spray tancatastrophe.
Caleb (04:11):
That happens I don't want people to think I'm no vain
enough to go, not not to allright, I derail, but that's cool
.
David (04:19):
no, it looks cool.
I think it's a good look, soanyway, it's in fashion for sure
.
You have witnessed how manyopen mic performances estimate
Back of the napkin.
Holy crap.
Years and numbers.
Caleb (04:34):
We got to do some maths.
Yeah, because let's see I'llspeed this part up, bro, take
your time.
Four or five open mics a week?
For how many weeks?
Let's say an average of fourmics a week.
For how many weeks?
David (04:46):
let's say an average of four mics.
Caleb (04:47):
Okay, a week with an average of, let's say, 12 people
on them.
David (04:53):
Okay, 12 that's 48, jesus christ.
That's a lot of hours.
That's 48 a week.
Sounds like you've been goingto six years of open mics.
It's a lot.
At 50 weeks a year, obviouslyyou're not going to every week.
So I would say you're somewherebetween 200 and 250 times 42
weeks.
(05:13):
Wow, wow, wow.
So let's just call it lowparameter.
Caleb (05:18):
We'll go 200 times 42 which is 8,000, that's a lot
never thought about it that way.
David (05:29):
Yeah, wow, wow, wow 200 times 4 is 800, so 200 times 40
is 8,000.
Ok, I just wanted to you're inthe top .001% of the global
population in open micwitnessing and I would say maybe
top 100 on earth.
Caleb (05:50):
There's thousands of us.
David (05:51):
Dude, I think you're number one in the world Number
one.
No, but so.
So this is an incredibleinsight.
And I think when you mentionedwhen we, when we had this idea
to come on, I had just done anopen mic I think it was my 18th
or 19th ever and then we juststarted chatting and I was like
(06:13):
I fucking hate open mics and youwere like I love open mics.
And I was like yeah, and so Iwas like, oh, this is going to
be great.
So it's like Crossfire on CNNright now.
Caleb (06:24):
Okay, no, no, we don't have to argue about it, but I
would love to know why?
David (06:27):
what did it?
What is it about open mics thatyou love?
Yeah, what have you learnedwatching open mics?
You know, I'm just gonna, I'mjust, I just want to extract
your experience and especiallyfor listeners, because there's
it's a ton of value forversioning stand-ups and just
people who are who are nowinterested in the whole world of
stand-up comedy yeah, what do Ilove about open mics?
Caleb (06:48):
oh, the humanity of it all.
Yeah, um, if you're a hardcorecomedy fan, you like I think
even through, uh, someone's likenervous jitters because it's
their first couple of mics cansee a good premise and a good
joke.
I love that.
(07:08):
I love to see people facingtheir fears right.
People who, um, do it one time,like these, these people that
come in with all sorts ofbravado, who you don't expect to
just crumble as soon as theyget up there.
That's great too.
That's a part of it.
Yeah, uh, this shot in freud alittle bit of it but also just
(07:31):
the the vulnerability of it
David (07:33):
be like yeah, big tough guy like this is hard and that's
okay and we support you anyway,man sweet, you're much more of
a sweetheart than I thought.
Now I feel like a real asshole.
No, not at all.
Caleb (07:43):
No, go, keep going uh and I love uh.
Also like people getting theirfirst laughs, like seeing people
light up.
They're getting their firstlaughs.
Um, I love uh watching thedownfall of uh, the itinerant
alcoholic piece of shit that youwish wasn't as funny as he is
(08:09):
and over time gets less funnyand less coherent.
That's a, that's a perfect openmic experience over the course
of years.
David (08:18):
You mean so he comes his first guy up.
There's all this like promise.
Caleb (08:23):
Right, and then his alcoholism.
The potential there's so muchpotential and he goes the other
way and then you realize thattwo years in he hasn't written
10 minutes.
And uh is doing and doing crowdwork at an open mic.
That is increased.
It's just devolving, yeah, weekover week.
(08:44):
Yeah, there's all that.
Um, that's a valuable lessontoo um it's all, it's all
learning.
Right, I love that?
Um, I definitely.
I think earlier we we assertedthat maybe I had some sort of
natural inclination to be funny,but I didn't recognize it and I
think that I would say, towhatever degree I've improved in
(09:06):
my stand-up, writing, delivery,performance, doing stand-up,
especially at open mics, I hadto learn it.
I'm a student of it.
None of it came naturally to meyeah, and I was as insufferable
as a lot of other open micersare when they start doing, you
know, hack shit, doing dirty,gross stuff for the sake of
(09:35):
being perverse and shocking.
And I still revel in that tosome degree.
I mean, like I've featured nowfor like national headliners at
Empire Comedy Club.
I've had the blessing to beable to do that and like my A
material I always pull out isabout putting an ice cream scoop
in my ass.
You know like I think that'sfine.
David (09:51):
It's true, it's the true story.
Caleb (09:55):
So, but that all came out of open mics and that culture
of the open mic.
David (10:04):
So where are you at in your career?
I'm gonna just, I just want tosort of oh, let's start there.
Where am I?
I mean, how many?
So?
So you started when?
What year?
2016?
Okay, and then you took acouple years off during covid
yeah, uh, I.
Caleb (10:19):
So I was, like in 2018, a semi-finalist at the Empire
Comedy Competition and like, dida half hour because that was
the prize for the semi-finalist.
David (10:31):
You had a half hour materials two years in.
Caleb (10:35):
I didn't, but I certainly performed for 30 minutes.
I did my time.
David (10:40):
That's amazing, that's terrifying.
Caleb (10:42):
It wasn't great.
Looking back on it it couldhave been a lot worse like, but
I was dedicated to going to themics and I would write a new
five minutes every week for myfirst couple of years whoa yeah
and no matter if it and a lot ofit.
You know ate shit, of course,but you never retested material,
never until I started gettingon shows in 2018, I would do a
(11:05):
new thing every week.
Okay, but hold on a second.
David (11:08):
How do you know that it's funny or not?
Because this is my big problemwith open mics Like, for example
, the one we just were attogether.
Those were all ostensibly otherstand-ups.
I was looking at the audienceas people were being you know it
wasn't bad some of the stufflooking at the audience as
people were being.
You know they were it wasn'tbad.
Some of the stuff, yeah, and noone's paying attention dude
(11:28):
everyone's like looking at theirown notes, so how on?
Earth?
Do you know that a joke is goodor not?
you don't not based on one's uhopen mic performance for sure so
do you wish you tried more ofthose out, or were you like the
pipe metaphor where you're just,I need two years of unclogging
my shit pipe I did need that Ithink, I did.
Caleb (11:48):
I think it was an outlet for me.
I think I also had no ambitionum, beyond getting better at
public speaking, right likebeing a little less nervous
every week, and, uh, the onlyagenda I had was to like say my
ideas out loud to a room yeah uh, for those for that time.
So it was a lot.
It was like an outlet thing andyeah, I was just writing uh and
(12:12):
like, uh, getting it out, but,amazing dude, once I started to
get shows, uh, then it's likewell, I would like them to laugh
.
Yeah, the open micers, I didn'treally.
I did care a little bit.
I wanted to like get into thosecircles and I wanted that.
(12:36):
I did want them to laugh, but Iwas more preoccupied with like
writing little rants.
David (12:42):
Yeah, I'm very ranty.
I was rant, ranty too and Ithought that was enough.
Caleb (12:47):
Yeah and no, we can't all be bill burr, but, um, you
don't.
And comics are not an audiencethat paid to come to a comedy
show either, so it's not doingyou any service.
Uh, you can glean plenty ofuseful information right from
(13:07):
just the performance, the, the Iwould say 80 of the utility of
going to an open mic for thefirst lot of time that you're
going to open mics is justcomfort, getting comfortable on
stage.
Yes, speaking, hitting thepoints you wanted to hit in a
bit.
That's like a huge chunk of theusefulness.
It's not about identifyingwhat's funny, and I would also
(13:30):
say uh, my, my point of view onit is I do, I do know that
something is funny when I writeit and it it's more dependent on
me successfully saying it,delivering it, than it is the,
the word.
Like I know, like you know, youcan identify a joke, you know
(13:52):
what the laugh line is right andand it might be not as funny as
you thought or it might befunnier than you thought, but
it's funny.
You know that when you write it.
David (14:05):
Well, it's like, you know it's a joke, you know that
there's a rhythm, that you havereleased the tension, and either
there's a laugh or not, but youhave stated a joke and if
you've done it with courage, youhave stuck it yeah and then
you're there to see, yeah, whatthe reaction is we.
Caleb (14:25):
I don't know if we were recording, but I was talking
about how I used to canvas andask people for money at the door
and when I was training collegekids to ask for money door to
door in our practice I would belike, how did you feel about
that ask when they would?
David (14:41):
get to the ask right.
Caleb (14:42):
Did you feel like it was a good ask?
Very similar, I feel like yes,you just know, I fucked that
joke up the joke is funny, but Ifucked it up or I nailed it.
Didn't get the laugh that Ithought it would.
Now we have to think what otherfactors went into why this room
of people in this context todaylooking at me, laughed only
(15:05):
this much at this thing.
That I think should be like thefinale to this big five minute
set or whatever you know, um,but you can't judge.
David (15:14):
Again, back to those open mics.
You can't judge the lack oflaughter on anything, that's
true, because no one's payingattention unless some people are
.
And like I've noticed as I'vegotten, I've progressed and
gotten objectively more, youknow, uh, playing by the rules
(15:35):
of stand-up and like sayingactual jokes, right, I?
I now see that some people arelike, you know, you hear a
couple and that's why therecording I you know gary
goldman's 366 tips, yeah, thatwe talked about.
Yeah, the number one is recordyour things and listen back.
And my friend al madrigo's donehbo specials.
He's like, he's like record andlisten where the laughs are and
(16:00):
where you're not getting alaugh.
That isn't importantinformation.
It's just gone.
Cut it, cut it.
I have the book Stephen King'sOn Writing, book that we were
both praising Same thing.
It's just like get rid of allextraneous everything, and that
seems to be a lot of the game.
It's more almost science, it'smore like tinkering in an
(16:21):
automobile shop.
Caleb (16:23):
Something that I recall from stephen king's own writing
is he describes it as likearchaeology like just brushing
with a toothbrush, uh-huh offthe stuff, right, revealing
exactly the structure of thething that's already there.
It's like a subtractivesculpture art, right.
(16:44):
Like you, it deforms.
In there, you got to chisel it,right yeah uh, and if you
chisel too much, you have adeformed thing.
If you if you don't chiselenough, you don't have a formed
thing at all.
David (16:54):
Yes, yeah, totally okay, so, so all right, I'm buying the
open mic.
The value of it, yeah, uh, and,and you're and totally about
getting comfortable.
I think, um, at my stage Idon't have the confidence you
have that the the joke is funny,meaning I can think it's funny
(17:15):
you know, but if it's, if itbombs, it bombs.
I know in talking ad nauseumwith so many people in the last
year, like sam morrell, who's sogood and so funny you talked to
sam morrell no, oh, he's sogood he's so good yeah whoever's
listening, go watch sam morrell.
Caleb (17:31):
But he was just in portland.
David (17:33):
Yeah, he was but I know that uh val over at the comedy
cellar sam his comedy sellershows is he's a writing machine
and he's, he's got, he's gotfive alts and he's like which
one val?
Which one should I go?
Which one did I?
Caleb (17:48):
go with, like what set, he should do.
David (17:50):
No, no, which joke he should do what's like, what's
funny like he's constantly andgary goldman's other tips is
just like the minute you have alaugh, like there's more laughs
in there.
We were talking about that.
There's more ways to you canprobably get three laughs where
you didn't think there was any.
You know and you can change aword whatever, but Val's
(18:12):
statement was Sam doesn't knowwhat's funny until he does it.
Caleb (18:17):
And he.
David (18:18):
I think let me preface it by saying I've witnessed people
testing jokes.
Caleb (18:26):
They're all funny.
David (18:28):
Yeah, I think what he's saying in his brain is what's
the funniest?
Caleb (18:32):
What's the one?
David (18:33):
Yeah, yeah, yes, and they don't know what the funniest is
.
They can think it is, but theyall know that they're jokes that
will get chuckles totally, yeah.
Caleb (18:42):
Yeah, that's the level, that's the only level of
confidence I have.
It's like this is not.
Nobody is going to throwsomething at me and tell me to
leave after I say this, you knowwhat I mean.
David (18:54):
Yeah, bare minimum.
They will see, they willappreciate the effort that went
into crafting a joke.
Caleb (18:59):
Quote unquote yeah, yeah yeah, I'm, and I'm by no means
like I would say samorelle,really brilliant joke writer I
don't know where thisdistinction lies in my brain
exactly, but like I don't thinkof myself as like a a great joke
writer, I'm, I, I am, I canwrite, I can articulate things
yeah, obviously to some degree.
(19:20):
Yeah like, but like it's notgonna be like 1970s joke book,
right formulaic that's done.
David (19:31):
That world is over.
Caleb (19:33):
But so I think like joke jokes a pretty nebulous, but I
don't think that I'm thestrongest joke writer.
I am a fucking weirdo.
And that goes a long way ifyou're able to bring people into
your point of view.
I'm much more interested inthat than I have endeavored to
(19:56):
nail the structural parts of it.
Not that I don't want thatchallenge too, um, and I do trim
some fat and think about whereto change words here and there,
but never been a great wordsmithme neither and I and I
constantly, when I wake up inthe morning I'm like what?
am I doing like I don't?
David (20:15):
because I have a friend who's a comedy writer
professional.
He's written scripts, he'swritten movies with ro De Niro,
like big comedy films, and Iwill reach out to him and I'll
usually record something in mycar or something.
And I'll be like what do youthink of this?
Does this feel hack?
And within like a nanosecondhe's got like three like it's
(20:37):
like blank.
That are just tight ass fuckingjokes.
Yeah, and I'm like is this your?
I'm gonna have him on thepodcast.
So I'm like is is your brainjust auto training joke.
It's like all day and he's likekind of yeah, I was like oh
yeah, because he's been in room.
He's been in sitcom rooms, youknow for that's his 8 000 you
(20:59):
know, thing of just likepitching jokes to 10 other good
comedy writers, yep, and so thatthat brain and I know that
that's not how my brain worksI'm more like with you,
philosophizing, thinking deeplyabout things.
My brain naturally goes toeither like fedex middle
management logistics, like howdo I get to my kid's school 20
(21:21):
seconds faster, or I'm just offin the clouds thinking of just
not jokes things I will say ifI'm writing every day I start to
get more of the downloads.
Caleb (21:35):
The accidental?
David (21:36):
oh that would be funny.
It's sort of like.
Caleb (21:38):
I have to keep my brain in that context do you feel,
when you're in that context,that sometimes they just appear
fully formed to you and there's,there's.
There's no wordsmithing,because you're just like well,
there it is.
I don't know where that camefrom rarely, but yes, it has
happened.
David (21:56):
And just like, yeah, that's what I want that yeah
because I'm I'm a lazy motherlike I want just to be
downloading constantly.
I know people.
Caleb (22:05):
Uh, I say this sometimes and I think that there's kind of
a worthy stigma surrounding it,like but?
But I think of comedy as like alow effort, high reward thing
really I do, yeah, which peoplehate?
I mean, I don't.
I haven't felt like going toall these open mics has been a
great effort, because I'menjoying it I genuinely enjoy it
(22:27):
, I love that's beautiful comedy, so it's not felt like but so I
have to pretend that that's thegrind.
David (22:34):
But I put in my reps uh-huh uh, but really like, I
just like writing, so I'll writesome crazy down, if I can get
laughs, that's how my friend,another comic, kevin christie,
who's been uh known forever andhe's a staple at the uh comedy
store in la and I'm like how doyou?
He goes up three times a week.
(22:55):
He has a, he has a neil brennanuh kind of mic, that that's all
for big stand-ups to test newmaterial.
And I was like how do you justkeep going?
He's like I don't know, I writeit and I'm like I need to see
if it's funny.
Caleb (23:10):
I just need to.
I relate to that Like yeah, areother people thinking this?
Or do they not realize they'rethinking this?
Or when I say this, are theygoing to think it's really funny
that I thought that.
Yeah, all that.
David (23:25):
I think I'm in the stage and I've said this on the
podcast but I think I'm in thestage where I'm trying to figure
out my life and story, almostlike in a memoir-esque way.
I'm like, how have I gottenhere?
Because I've kind of been a a Idon't know.
I just try to live in themoment, try to have fun, try to
do what's enjoyable, and then Ikind of wake up and I'm like I'm
(23:45):
46, I have a wife and kids, Ilive in maine.
Like how the fuck did thishappen?
Right and um, and so a lot ofthe writing that appeals to me
is kind of mining my personalexperience, which I know from
stand-up point of view.
Is there a?
I sense this, I don't know why.
Is there like a looking down onpeople who kind of like bring
(24:08):
their own personal life?
Is there like a snobbinessabout that that you are aware?
Caleb (24:16):
of.
Maybe what I think you might besensing is that low level open
micers are often really have ahard time being vulnerable, and
that they have always had humoras a deflective self-defense
mechanism.
And so what they?
(24:36):
When you talk about your life,they see it either as
self-absorption or vulnerabilitywhich terrifies them.
And they will then go to themechanism they've relied on
their whole lives, which is tohumiliate, not humiliate it.
(24:56):
What's the word?
What's the word?
They need to put it down yeahright, they need.
They need to be like oh this,you're talking about your kids.
Yeah, gay yeah, I mean yeahlike um, I don't know if it's
snobbery, I think it's actuallyjust a kind of neuroses that
(25:18):
they they can't take anythingseriously.
How unfunny would it be to likethink you know?
This, I also think, is why,like the people, the, the rare
comedians who like able to dodeep social commentary and like
have a point, are people thatare really really friggin funny
but are not debilitated by theirfunniness you know what I?
(25:40):
mean like uh, you'll meet peopleyou probably know, comedians
who can't turn it off never turnit off it's annoying and it's
annoying, it's like a it's it'skind of tragic yeah, it's like
you'll, you'll, they're justbidding all the time all bits
all the time and you can't evenhave a conversation with them or
(26:01):
like shit will be going on intheir life and you are trying
for just a moment to check inwith them as a friend and
they're like mom died, whatever,dude, it's not no, big deal
like and you're, that's actuallytragic.
So yeah, I don't, I don't know,I can't speak to like broader
comedy community outside of theone that I've experienced, but I
(26:22):
have noticed that that happensin the main comedy scene.
There are a lot of comics whoare just not able to get
vulnerable with you yeah, somaybe that's what you're sensing
yeah I've done a lot of likemining of my personal experience
too.
You don't see it as much.
I mean, we're all coming fromour own point of view.
(26:42):
It's all autobiography, yeah.
So if you're doing itintentionally, I think you
probably have a.
David (26:50):
You're a little head up on the folks that are doing it
unintentionally well, it's agood segue because I want to
talk about this idea of in ourcars we're like amazing and we
rip and like I've had rehearsalslike a half hour before an open
mic where I'm like ooh, fuck,yeah, it's going to crush, let's
(27:13):
go, baby, of course.
And then you get in this roomand the energy of the room and
you're like nothing I did in mycar will work, because the
energy is totally unmatched tothis.
Somehow I have to take theenergy, transmute it, transform
it into something where now myset works.
Can you speak to this idea oftaking control of a room or
(27:43):
being having to match your setto something in ineffable,
almost in a room?
Yeah, what, what do you knowabout that and what, how do you
see it and how do you deal with?
Caleb (27:56):
it.
Wow, yeah, no, that's a big.
I mean in the vacuum of yourcar you were all crushing.
If we could, if, if we couldall be who we are alone in our
car, we would all be stand-upcomics professional.
Yeah, if we could do that infront of people, that would be
(28:17):
pretty wild, I don't.
It's an interesting way to frameit that you that you framed it
like is it that you need to takecommand of the room and then
transmute the energy, or do youneed to meet the energy where
it's at?
And I think that's like a great, that's a great frame.
It's probably something likeboth at once.
Like I think maybe takingtaking command of a room
(28:40):
involves just instantlydemonstrating in your body
language, your countenance, yourcadence, immediately your
cadence, that you are likeyou're a part of the room.
You recognize the energy that'sin the room and you're
consciously bringing it to whereyou want it to go.
(29:00):
For a moment you have the micright, like what that it is.
That feels ineffable to me toto really describe how people
can do it.
You witness it, you recognizeit when you see it, but you're
but it's.
You know it would take, I think, a bunch of analysts could talk
about.
Oh, the body language and theirtone, or like, I have a deep
(29:22):
voice, or like, like, what is itthat is commanding the the
attention of the room?
I would stop just short ofsaying it's magic, right.
Cause there's definitely thingquantifiable things that we
could like appreciate about howit transpires that someone just
can go up there and in a roomthat was could appreciate.
About how it transpires thatsomeone just can go up there and
in a room that was gigglingabout stupid puns a moment ago,
(29:47):
talk about some serious topic,and get huge, crushing waves of
laughter from a room, just toreally quickly take control of
the room.
In that way, we are trying tomake people laugh, make them,
make them, making them do it.
Uh, it is an involuntaryresponse laughter right, so like
(30:10):
um I don't know.
David (30:13):
Yeah, that's such a cool answer.
I think it made me think of theadvice or that I've read, or
whatever, that you know there'scertain techniques, right, like
the person before, if you'vebeen listening, usually there's
a way to tie your first joke towhat they've done.
Yeah, uh, gary goldman's advicewas usually, I find it very
effective to get up there andmake an observation about the
(30:37):
either the room or the the stageor something that no one stated
.
That is honest and funny.
Yeah, and and I will say thatthe blink moment it's blink
moments when you see aprofessional get up there
because they are exuding likeyou're in safe hands and it
(30:58):
usually is immediately they finda way to make everyone laugh
and they're just like oh okay,this guy is funny and he's
comfortable and he's poised andthis is a professional.
Now I can relax and I think if Ihad to state what is the value
(31:21):
of open mic land?
It's getting good at that.
It's just going into hostileenvironments and being like I'm
gonna learn how to in 10 to 15seconds, 20, 30 max.
Yeah, just have everyone on myside yeah, well said.
Caleb (31:39):
That is a great insight on the value of open mic, I
think.
That is one of the definitetakeaways over time that you get
is that it's interestingbecause I see a lot of the
national headliners that comethrough Empire Comedy Club.
David (31:57):
Yeah, just for people listening, Caleb works at the
Empire Comedy Club, which is theone real comedy club in.
Just for people listening.
Uh, caleb is works at theempire comedy club, which is the
one real comedy club inportland, maine.
Yeah, and you guys get bigpeople yeah, huge names huge
names come through punching wayabove our weight class.
Caleb (32:11):
I would say for a 130 seat little club to have like
joe List annually come through.
I have had Big Jay Ogerson dolike four sold out shows
Incredible.
David (32:27):
Who is the guy that you took me?
Caleb (32:29):
Kyle Canaan yeah, awesome , we're going to have Doug
Stanhope in October, I think.
Just yeah, awesome.
Legends Ari Shafir we hadReally cool, really cool club.
Wow, I got derailed.
What was I going to say?
Oh, just that, those folks,those heavy hitters, there's a
(32:50):
certain degree to which theystill do that because it's like
a reflex to them.
I think at that point, whenyou're a pro to riff on the room
in in some way, to do likeyou're saying, uh, in the first
10 or 15 seconds, just make sureeveryone's like, yep, we're in
good hands, this is a prothere's a degree to which they
have less of an impetus to do itat all because they're them
(33:14):
just being the ticket that youbought yeah it already kind of
did that for him yeah I see thisespecially with, like lucas
zelnick, rachel uh, I almostsaid rachel rachel scanlon, uh,
people who have big onlinefollowings, who are there for
them.
That are their fans, who watchtheir content, their podcast,
(33:36):
their clips, their crowd work.
They are so excited to be inthe room with them.
That it's immediate, it's justimmediate.
Whatever the first thing out oftheir mouth is, it's gonna get
applause.
David (33:50):
You know that's sort of the world of the netflix special
, it's like yeah, you know whatI mean.
Like all those high ticket,those people love this comic.
Caleb (33:59):
Yeah, they're like bitter open micers who have no right
speculating.
We'll often be like at thatlevel.
How do you even know if it'sfunny?
They're just laughing becauseyou're Tom Segura.
It's like okay, dude.
David (34:13):
Sure yeah, keep telling yourself that.
Caleb (34:16):
Yeah, no, it's fun, it's a wow.
Yeah, that's a really great one.
I'm gonna tell noobs that aboutopen mics.
It's like getting comfortableon stage is the value of it and
learning how to uh bring theenergy of the room where you
wanted to go and like littlethings like that.
You also pick up from hostingshows yeah, there's a lot of
(34:39):
value to hosting, isn't there?
I've hosted a ton of shows andthat was something I had to.
To learn was like what?
I have to change my opening bit.
I have to do the kind of calland response like, oh, come on,
guys, we can do better than that, or something to that degree.
I have to ask them aren't youguys excited?
You know I have to uh, freaking, project my voice a little more
(35:03):
and like yell yeah um, that allis valuable.
Or just like the economy ofwords, like to to get through
house rules, even like if youfucking fumbled the house rules
and then five minutes later youget on stage to host.
They're already like who's thisfucking guy?
David (35:25):
yes, I have.
I'm trying to figure out a way,because when I speak there's
certain moods and you know whenyour brain's cooking that you're
you know more, more articulate,and then there are times where
you're, you know, tired orwhatever, and like I am now,
like it's like halting and youdon't really know what you're
saying.
There are certain comics likewoody allen comes to mind other
(35:49):
where, like almost the whole the, the, that thing becomes the
part of the act yeah and there'sa part of me that's like I
think I'm gonna have to do thatbecause totally I can't be
crispy cream.
You know what I mean?
I I could just yeah I don'thave that and I, when I listen
back to my sets, like I'm thefiller words, I'm like dude,
(36:10):
what are you doing?
Like the amount of filler words, and sometimes not yeah and I'm
just like shit.
Caleb (36:16):
Like because the filler words deflate and I think they
show amateurism and you'relosing trust if you're going uh
uh, At the very least you'rethinking about the next word
you're going to say that goesaway just from repetitions to a
certain degree.
David (36:35):
Yeah, and there's stories I've told maybe 10 times where
I know the story and I canchange a little bit.
And that's a lot of what it isright that fluidity is good.
Caleb (36:44):
there's also the other side of that coin where, uh,
you've told that you're tellingthe joke for the 50th time and
it comes off too polished, right?
So, um, like, really, reallystrong joke writers I think have
to will intentionally include afiller word.
Yes, I have a bunch of bitswhere part of it is that it's
(37:08):
like oh, I'm, what was I goingto say?
Oh right, the punchline.
David (37:12):
Like I knew exactly what I was going to say.
Caleb (37:15):
Knew it right yeah, so it is.
I've noticed.
So when I was I don't know whyI keep coming back to this it
was valuable for my stand-upwhen I was canvassing, knocking
door to door.
I was training people to dothis political, political
donations.
David (37:30):
Right, talking about my version of stuff yeah, it's not.
Caleb (37:34):
You know, nobody wants you interrupting their dinner
time and and it's hell.
But one of the things that Isaw was completely unhelpful in
training people how to canvaswas pointing out filler words.
It would just completelydestroy the confidence.
David (37:52):
Yeah, because they would say one and then they'd panic.
Caleb (37:54):
Yes, so it was like not the feedback that a lot of
people needed to hear, that, um,I wouldn't, I wouldn't worry
too much it's so funny.
David (38:03):
You say that because I remember my third open mic or
something, and you may have beenthere.
It was at empire and I it wasmy first time, maybe, at empire
and I was like, oh, my first two, there were so many uhs, it was
so messy, I gotta be chris,like the pros, and I went and it
was like this robotic,perfectly stated thing that was
(38:24):
just not.
Not a single laugh, you know,like just like just crickets for
five minutes, dude, yeah, and Iremember being like, okay, I
guess crispy isn't the wholeRight, you know, so, so, and now
, yeah, the, the, the wholething.
One of the guys that I reallylike, uh, his name's Fox Uh, I'm
(38:51):
spacing his first name, buthe's, he's an LA really good
writer.
And Kirk Fox, uh, if you'venever heard of him, you should
check it out.
Go to his Instagram.
Caleb (38:59):
Yeah, and Kirk Fox.
If you've never heard of him,you should check it out.
Go to his.
David (39:01):
Instagram.
Yeah, really funny and he's gota really good reputation.
He started late, like hestarted he was a tennis pro and
then he started in his mid 40sand now like is big with all the
big hitters.
He had DM'd me because we havemutual friends and he was like
I'll help you write some jokes.
And I was like I got to learnhow to write a joke for us
(39:21):
before I started pulling likesuper pros, you know.
Caleb (39:24):
Sure.
David (39:24):
But he said um, he said just talk it's, it's like it's
just talking with people asopposed to at them, and that was
like the only thing he said andand that you know, it's like
this simple thing that you'relike, that's like a nothing
(39:44):
statement, right, right, talk atthem.
Well, of course I'm talkingwith them, but there's something
there that's very deep and I'venoticed in all my open mics.
If I go up and I have some setin my head and I just like to
get through it properly, it it'snot nearly as good or as
satisfying as being messy, but Ifeel like I'm like dude, we're
(40:07):
talking and we're having a we'rehaving a little chat ski right,
you want to guys have a littlechat ski with me up here you
know, like that kind of thing,and you can say it, you know.
And then then you feel likeafter our interview to like I'm
gonna have being a great movebecause I've connected with you
in a very real way yeah and thenthe point is like you can do
that on stage, yeah, and anytimeI I just go up with the
(40:29):
intention to connect.
There's just more goodwillcoming my way, you know totally.
Caleb (40:34):
Um and that'll also change what you want to write
about, because, uh, if you'rewriting autobiographically, it's
like well, we got to talk abouthow this is like the human
experience, not just myautobiography, right, but like
what's funny about this thateveryone can talk about, or, or
if you're doing, or you're atleast more self-aware to be like
(40:56):
that was just just this is ajust me experience, right, y'all
like in the room.
And then there's also a thingthere, uh, which I've heard like
comedy teacher types talk about, where you're like training
them that their input is a partof it.
Uh will encourage the laughterand reactions.
Who's Oz?
If you're having a dialoguewith uh, you're asking them, you
(41:20):
hear it Standups do this allthe time, even if it's
completely rhetorical, is like,right, like yeah, what.
Nodding with folks just toconnect that connection as
opposed to just reciting at them.
David (41:33):
Yeah.
Caleb (41:34):
Uh, reading lines to them .
David (41:36):
Yeah, I would say, the premise setting up is always in
the sort of you language, likeyou know, when you blank.
Caleb (41:48):
Now I just I want to write a five minute set where I
only say when one goes to thepost office, when one, when one,
no, you, yeah, so I'm going to,because we're I'm going to be
nearing my children's schoolpickup, so I do have to.
David (42:07):
Kind of I could talk for another couple hours.
Hell, yeah, if I may, I thinkpeople would be interested.
You've witnessed.
Did you watch my set onThursday?
Yeah, it was about meditation.
Yeah, like just you know thepremise is, I've done so much
(42:30):
meditation to try to become abetter person.
All I'm doing is becoming moremindful of what a degenerate I
am.
And then you know variousthings.
I would be very grateful if youjust either, maybe in the
context of, like, what are younoticing that I'm doing?
Well, what do you?
What are you noticing that Ishould work on?
(42:52):
And what are you noticing Like,is there any raw?
Is there anything that you knowhit you as like a I don't know,
kind of a, an area that isworth mining, if you will.
And I don't want to put you onthe spot because you may not
even remember what I said oranything I did.
Caleb (43:12):
But any kind of impression.
I've always had positiveimpressions of your sets.
I feel like I'm not usuallydigesting people's sets in a in
a way of like oh how can I givethem tips, right?
Yeah um, nor am I super, supercritical if you, if you're doing
(43:35):
so, what maybe?
Maybe the feedback then is Ithink you're doing a lot of the
fundamental stuff right, whichis just that you're, and maybe
this is learned.
I remember your MillennialsNeed to Fuck More.
First, open mic, hot take asbeing really funny and it going
well.
David (43:52):
Oh, interesting.
Caleb (43:53):
I don't remember any crickets sets from you, but I
haven't been at every single one.
David (43:58):
You haven't been at every one.
Caleb (43:59):
No, the first yeah, I would say you're doing a lot of
the fundamental things right,and maybe just from this
conversation too, I would say,if you've got a premise that's
that loose, it feels like you'reopening yourself up to the
possibility that when you get upthere, what you wrote down
isn't what you're going to sayand that that kind of
(44:21):
playfulness can go a long wayand create more connections and
have a more conversational uhfeeling, which can be really,
really fun for people with,where you still have a few punch
lines in your back pocket todeploy, if the right energy and
moment appears in, in justbringing the topic up with
(44:44):
people, like if the premise is.
I've done all this meditatingand now I'm just more aware of
what a degenerate I am.
I've done a lot of open micsets with nothing more than a
premise.
People sometimes would callthat like writing on stage.
I don't know to what degree Ido that, but sometimes my only
goal for an open mic set is tosay it out loud in front of
(45:06):
people in a room, see whatreactions just the premise
starts to bring and go fromthere.
David (45:13):
Do you start doing crowd work a little bit?
Caleb (45:16):
after I will occasionally .
I don't know how useful thatalways is for writing, but I
guess what I'm saying is likeoccasionally, I don't know how
useful that always is forwriting, but I guess what I'm
saying is like how comfortableare you with, like the
extemporaneous?
Writing yeah based on a premise, because I think that you would
really thrive in that, and thenyou come away with something
that you could do lessimprovisationally later oh, this
(45:39):
is beautiful because I that's areally cool idea.
David (45:44):
It's ballsy and I I think I it's ballsy in the sense that
you're kind of like I don'tknow what I'm gonna say yeah,
but it's low stakes it's superlow, you know I think my
challenge is because I'mrecording them all and I think
it the the premise of thispodcast was that I share them
all.
It feels weirdly high stakesevery single one but I don't
have to share and I've stoppedsharing every open mic.
Caleb (46:07):
I do, but you don't need to go like full.
David (46:10):
hey, let's workshop this premise together, guys, yeah,
yeah, yeah.
Caleb (46:13):
But you don't always need to know the punchline.
If you mull over the premiseand what you think is funny
about it, you can, I think.
David (46:23):
I don't know, that might be horrible advice, but no, no,
I don't think it is, becauseultimately I get my enjoyment
and I try to north star, likewhat is exciting about this for
me?
Yeah, and I think one of mygreat challenges is is repeating
jokes.
I don't like doing it in life.
I mean there's a couple thatyou do because it's almost like
a parody of the joke.
Yep, you know, like one of myfriends has a line where where
(46:48):
his pickup line, oh no, he'll bewith a group of his buddies and
and there'll be a table ofgirls like with an earshot and
he'll be like guys, guys, enoughwith the fucking donkey dick
jokes.
It's old, you know, so they canhear and like that dumb shit.
Like I could hear it 50 timesand still find it you know, um.
(47:12):
So there's certain jokes which Iwon't tire of saying, I would
say on stage, but for the mostpart there's a sort of a almost
like a shame that I'm doing thesame thing.
And that's a problem withstandup, I think, because you
are all constantly tinkering anddoing the same thing.
Caleb (47:30):
One of the things.
David (47:30):
That's hard.
While you think about aresponse, is that I that that
gave me a bad feeling waswatching Louis CK do this
amazing set and his performancesare so good because they're so
coming out of his head likethere's such a.
I'm talking with you and thisis just coming out of my mouth
(47:51):
for the first time and then thisdamn instagram person put on
another night the same exactthing and it was like exactly,
yeah the same.
Caleb (48:01):
He's master of that.
David (48:02):
He's a master, it's every nano beat is mapped out oh yeah
and I was like, oh shit, like Iwonder if that's obviously he
enjoys, that, he obviously has aprofound love.
I want to.
I I worry that I won't havethat love and I have another
friend who started stand-up.
He's like really famous daxshepherd and he he started uh
(48:24):
doing he.
When I said I was going to dothis project, he was like I did
stand-up actually right when mykids were born and he was like I
challenged myself.
I just do new stories everynight and he got hooked in Vegas
, but he never repeated it rightand we sort of have a he's a
master improviser, sure, uh.
But anyway, my, my that'sreally my long-winded way of
(48:44):
saying there's concern I havegoing to bed at night.
That, like stand-up, is anamazing art form that I'm
clearly intrigued by, but I'mjust like, oh shit, like yeah,
is it?
Is it going to be enjoyable toto?
Keep repeating to to have sometight 10.
That I repeat 30 times yeah, I.
Caleb (49:06):
So I'm only recently beginning to struggle with this
because it's been.
I have like I've got this like20 minutes.
I have like that.
I do the same way every timeand I've started to get sick of
some of them.
I hate all of those jokes nowto some degree, but I, I would,
(49:26):
my, I don't know, I would see mysuggestion would be like that.
This, uh, stand-up versus improvdichotomy is a false one, and
both muscles are reallyimportant to to exercise and
that you, like I said I did anew five minutes for like every
week, multiple open micssometimes for like two years.
(49:49):
I was not interested inrepeating stuff.
That's wild, and I had the samesort of fear too.
It was like, well, that's notgonna be fun, like I said the
thing and I don't need to goback there.
But there is a ton of value, ofcourse.
That is.
The stand-up game is in thetweaking and the wordsmithing
(50:11):
and then performing it as thoughit's the first time you've ever
said it every single time.
There is a lot of value in that, but there's still, I think,
because of that energy in roomswhere we keep talking about,
there's a ton of value in theimprovisational stuff as well,
and like you don't need tobecome a crowd work guy to mine
(50:38):
the value from whatever you canget out of that, right, I would
say.
So I think, think you, and alsoI mean you've done how long
have you been doing this nowlike, well, I did my first open
mic about a year ago, but I'mstill below.
David (50:54):
I'm nearing the first 20 open mics yeah, yeah, that
you're.
Caleb (50:59):
You're your first 105 minutes that you write aren't
going to be the ones that youwant to like, immortalize, yeah,
you know, don't be so sure,yeah I, I think I'm almost done.
David (51:14):
I think my life's work's almost complete so I start
commissioning the equestrianstatues well, I, exactly, I, uh,
no, I.
I was down at the bitterfordopen mic, uh, mulligans or
whatever, and and it was thefirst time I had a real set,
that was like I, I reallyfocused on the writing and and
(51:37):
then all those guys asked me tocome do like the real you know
set or whatever where there'spaying customers yeah which was
which was a really cool feelingof, uh, validation of the hard
work that I felt like I had done.
That being said, they're like soyou got 10 minutes right and I
was like what?
So now it's sort of like okay,I had this thing that was
(52:00):
probably took six minutes toperform, but if I do it right,
it's probably four minutes orthree and a half, yep, and now I
need another seven to kind ofbe that minimum.
Would you say.
10 minutes is kind of theminimum where you can start
being asked to to join shows uh,no, we'll do guest spots that
are five on some showcases yeah.
Caleb (52:20):
Yeah For, like much newer people, people who want to see
how they handle it.
Yeah, 10 feels really short tome now.
Yeah, but it isn't.
It's so much time you can do somuch.
Yeah, just watch the first fiveminutes of any of your favorite
specials.
There's so much.
David (52:38):
There's so much packed in .
That's what my friend Kevinsays.
Caleb (52:48):
He so much packed in and that's my friend kevin's day,
he's just like, at the end ofthe day it's last minute.
Yeah, you know, and you're like, oh, and those guys, that's
what they're doing.
This is another great thing Ihad early on was that at bull
phoenix in portland when thereused to be comedy upstairs run
by this awesome guy, mike mikelevinsky, I think his name a
really cool guy he would do atthe end of their showcases,
anybody in the audience whowanted to could take the one
minute challenge and he wouldgive a dollar to whoever had the
(53:08):
best one minute.
That's fun, I think.
Starting to think about minutesof comedy, because one time I
was like I'm going to win theone minute thing and I went
there and this awesome comic inPortland, amelia, that I love,
just showed up out of the blueand everyone was like, oh my god
, amelia is making an appearancelike we haven't seen her in
(53:30):
months because she kind of comesin and out, she's got a busy
life, uh, and she just crushedme oh based on like telling just
a story from her day.
Like casually, I was like fuck,I wrote six ten second jokes for
this and it was really reallygood lesson and I have a file on
(53:52):
my phone to this day that isjust one minute challenges where
I'm thinking in terms of laughsper minute.
I'm not a one-liner guy.
I don't.
I don't even think of myself asa great joke writer, but it's.
It is important to think aboutit minute by minute.
And even if it's a, I'mnotorious among the comics in
Portland that I work with a lotfor just making a thing way too
(54:14):
fucking long and just havinglike a seven-minute rant about
Amish people that I don't needto have.
So I constantly need to bethinking more, yeah, like what's
the tightest version of thisthat I don't need to have?
So I constantly need to bethinking more, yeah, like what's
the tightest version of this?
Where's the setup, where's thepunch in it?
And that's a really funexercise to do is just like give
yourself a one minute challengeand then write 10 of them and
(54:37):
then you'll be all set for yourcomedy mill gig.
David (54:40):
Nikki Glaser was on Howard Stern, yeah, and she just
explained one regret she had,which is that she didn't ask
friends to help her with hersets earlier, like she just did
it all alone and she thinks it'slike so much more fun.
I would have gone so muchbetter, so much faster.
Yeah, and that was all I needed, because I've been trying to
prove to myself that I could begood on my own and, like you
(55:00):
know, I want this all to be me.
It was like almost egoic andthen I started just saying fuck
it, reaching out, sending a rantto a friend what do you think
is this hack?
And just the joy and enjoymentand the just collaborating and
not being so precious, totally.
And the other thing my friendsays like dude, if you're in two
years and this is your, yourwalking testament if you're in
two years still performing thesejokes that you wrote in your
(55:24):
first year of stand-up, like youare failing dude, right, like
it, that is not the game.
And so I think, like you, youjust did it, naturally, without
that advice.
You just kind of had anintuitive sense like I just
gotta fucking get unclog thepipe.
Man, I, man, I did, yeah.
Caleb (55:41):
Yeah, and I've only recently become less precious
about like accepting tags frompeople.
David (55:48):
Only recently.
Caleb (55:50):
Yeah, so I totally agree with that.
It resonates that you're goingto have awesome people around
you who are very clever too, andyou're going to hopefully
you're like carpooling to somegig an hour and a half away.
You got all that time.
You're just riffing like stuff.
That's the best thing ever,that's if you can share even a
(56:12):
microsecond of that joy thathappens in a car, just driving
with another comic on stage likedon't deprive audiences of that
.
It probably was really fuckingfunny.
David (56:24):
Yeah, I think it would supercharge development to just
be around comics all the time,and I think those guys are you
know I think the top guys are.
That's their friends.
They're just constantly hangingwith them at the clubs.
Caleb (56:37):
Yeah, they talk about the good hang, the other part of
this work, the social networkingaspect of it, where it's like
you can be really really funnyand talented and, uh, absolute,
uh, displeasure to be around andthen you're not gonna get far
yeah, uh, that is something I'vehad to reckon with too.
(57:00):
Not that I'm like not fun to bearound, but I'm just like not
as motivated by companionship asI ought to be, and I've worked
on that.
David (57:08):
Are you a lone wolf?
Caleb (57:09):
Definitely like a homebody and just very isolating
, self-isolating.
Yeah, I've working at the.
Actually working at the clubhas helped with that a lot too.
It's like now these people arelike my coworkers.
I'm not going out to the micand sitting alone, I'm like
(57:30):
behind the bar.
There's like a customer facingaspect to it.
David (57:35):
That's four times a week, right?
Yeah, four.
Caleb (57:39):
Monday, yesterday went pretty well.
It might be five soon, but yeah, but it's been good for me.
I completely agree.
We all need to be bettercollaborators with one another
and just share in that, in thejoy of it.
We all have this shared joy forhumor and funny and the craft
like 100.
Yeah, nikki blazer said uh,she's.
David (58:01):
you don't blame an interior decorator for, like,
borrowing the tapestry or thefabric, and so she sees it more
as like you're a designer asopposed to like, and I thought
that was cool For her to saythat.
You know it felt from someonein her position.
(58:21):
It's probably more better forher career to be like.
No, this is like me, like yeah,there were writers at the
golden globes, but like that wasmy stuff, you know.
And she was just like no, um, soanyway, well, caleb theodore
sherman, thank you.
Where can people find you?
Your instagram is caleb thesherman at caleb the sherman
(58:45):
yeah and do you have any of yoursets on uh on the interweb?
Caleb (58:49):
I do have quite a few clips up on youtube.
David (58:53):
Uh yeah, on youtube as well, on instagram too oh,
instagram is the place to seesome of your stuff talk.
Caleb (59:00):
I went through phase I was throwing content up like
three times a week and veryquickly got discouraged by that.
But oh, it's awful the gramsthere, and you can know I'm
always at empire comedy club inportland, maine go say hi to
caleb at the empire comedy clubin portland.
David (59:17):
Yeah uh, he's tall, he's, he's handsome, he's fit, he's
what?
220 6'3 did you?
Caleb (59:24):
did you know that because I say that in one of my jokes,
or did you just?
No, I'm a weirdo I I just 6'5220 6'5, 220.
David (59:31):
Guess what big boy I am?
Caleb (59:33):
6'4 and a half, 230, dude taller than me I'm like a half
inch taller maybe I don't know,maybe you're 6'5, I'm 6'5, yeah,
you're tall, you're taller, Idon't know, I don't five.
David (59:43):
Yeah, you're tall.
You're taller.
I don't know.
I don't know it's all posture,but I, um I'm on an all sugar
diet and I'm just gaining rapidweight, so it's great.
Caleb (59:51):
How many large Papa John's pizzas do you eat per
week?
David (59:55):
Oh, no, no, pizza dude, I'm not allowed to eat that.
No, no, I can't eat.
Caleb (59:59):
I'm like I can't eat grains Averaging more than one
large pizza myself a week.
David (01:00:05):
Well, it's a nice price right, it's good value.
Calories per penny.
Caleb (01:00:10):
Yeah, yeah, yeah, 2,500 calories 2,500 calories.
David (01:00:14):
What is it?
You probably have a coupon.
It's like eight bucks, right.
Caleb (01:00:17):
Nine ten.
If you're loyal, you get a freemedium pizza from Domino's
every like 20 pies.
David (01:00:25):
Dude Dom loyal.
You get a free medium pizzafrom domino's every like 20 pies
do domino's I miss domino's.
Caleb (01:00:29):
What's your go-to pie?
Uh, in portland.
Well, papa john's, what's yourgo-to?
Pop it, oh, and pop just garlicstuffed crust with uh so
there's cheese in the crust?
David (01:00:36):
oh yeah, and it's garlic.
Sure, I think they mean theyclaim to have garlic night
terrors.
But and um, you can't eat grains, your uh well, sugar, no, no, I
, I yeah no, I, if people whoknow me well like I'm always
doing, uh, some sort of weirdthing to try to, you know, try
(01:00:57):
to feel better.
You know I can't do drugsanymore, so it's like you have
to feel better for what you eat.
Super fun, yeah, this was a lotof fun.
Yeah, so I'll be seeing you.
I'll see you at Empire man.
Hell.
Yeah, all right, brother, peace.
Well, I hope you enjoyed thatas much as I did.
(01:01:18):
I'm leaving a little Easter eggfor everybody, because I assume
Caleb's parents would probablylisten to most of this, but if
they're anything like my parents, they would tune out eight to
ten minutes in.
So I've left an Easter eggwhich they will regret not
hearing, because it's a secretthat Caleb revealed probably
about seven minutes into usgetting to know each other, and
(01:01:42):
I'm going to leave you with thiswonderful little clip.
One more thing I'll say aboutCaleb.
In re-listening to this episodeand getting it prepared for the
World Wide Web, his words seepinto my consciousness, and so I
found myself today, wednesday,writing new stuff for an open
(01:02:07):
mic, and because of the freedomwith which he explained his own
open mics, it inspired me.
Caleb inspired me to take somemore risks on stage and to not
be so hung up on being perfector looking professional.
Open mics are low stakes andthey are a place to push the
(01:02:30):
envelope and to explore If youcan be terrible for four minutes
and 58 seconds, but if there'sone nano moment where you
realize something, you discoversomething, then that time is
worth it.
I think that's what I'velearned on this from this
interview.
This isn't about becomingperfect.
(01:02:51):
This is about doing it your way, and there is only one place
left where you can trulyexperiment and do whatever the
fuck you want, and that's openmics.
So what am I saying?
I've gone from an open michater to someone who mildly
(01:03:15):
respects them.
No, I see a lot more of thevalue and I thank Caleb for that
.
Is there anything you've hiddenfrom your parents that you'd
like to reveal right now.
Caleb (01:03:25):
I've reveled in revealing those things to them over time
so much that there's almostnothing left there's one thing
that I do, that I do bit abouton stage all the time that still
hasn't made its way back tothem.
That is the last.
What is that bit the?
(01:03:45):
Uh, it involves butt stuff yeah, anal.
Yeah, okay, yep, and umreceiving or giving um, being a
teenager that was shoving randomcommon household objects in
their butt, in your own butt, inmy butt, at a boy, yeah, at a
boy, as one just exploring thebit is about.
David (01:04:02):
It's like a psa to parents, so that In your own
butt, in my butt, atta boy, yeah, atta boy, as one does, just
exploring the wonderland, thebit is about.
Caleb (01:04:05):
It's like a PSA to parents, so that hopefully they
go home from a comedy show andthey see everything in their
house in a new light Glistening,have some kind of a talk with
their kids.
David (01:04:17):
Harm reduction, I'm just doing a service.
Yeah, I was imagining yourparents hearing the bit and then
looking at all the householdobjects.
Caleb (01:04:26):
In particular, a specific ice cream scoop that I know is
still in their silverware drawer.
David (01:04:32):
Good Lord.
Caleb (01:04:33):
Yep, it's out there now.
That's fantastic.
David (01:04:35):
It is most certainly on the pod.
Yeah, it just makes me want towish everyone an incredible week
(01:04:56):
full of anal venery.
Hello, welcome back to another very special episode of
Starting Stand Up at Maine withDavid Walton.
Today I, david Walton, amsitting down with Caleb Theodore
Sherman Very powerful name fora powerful man, a fascinating
figure in Portland Maine'scomedy scene.
(00:22):
Okay, caleb works and performsat the Empire Comedy Club.
It's a 140, 30-seat theaterthat gets huge names.
Caleb has been there since 2016.
He was born in 1992.
He was born to mental healthprofessionals in upstate New
(00:42):
York.
Caleb grew up in the Poconoswith an almost clinically
perfect upbringing His words,not mine.
He's been nurtured by veryconscientious parents who have
obviously screwed him up becausehe's in stand-up.
He studied philosophy incollege, which is a worthless
degree, as we all know, but hediscovered through a poetry
(01:03):
reading, his love forperformance.
These poetry open mics, but hefound himself more interested in
getting laughs than fingersnaps.
Since 2016, caleb has seen itall, and when I say that I, I
mean it quite literally.
I won't give away the number yet, but I believe Caleb has seen
(01:25):
more open mics than any otherhuman being on earth, and we had
a fascinating conversation.
I loved it.
One of the coolest things aboutdoing this is that I get to
meet people like Caleb, not knowhim, invite him to my home,
trust this man with long hairdown to his nipples who looks a
(01:47):
little bit dangerous in a goodway, but then turns out to be a
extremely soulful, kind,intelligent human being.
So what you're about to listento is two men getting to know
each other for the first time.
So, without further ado, pleaseenjoy this conversation that
(02:08):
dives deep into the craft ofcomedy, specifically open mics
and their value.
Here is my chat with CalebTheodore Sherman oh man, that's
(02:40):
rubbish.
Caleb (02:41):
That's rubbish.
Was born.
I was born in a bathtub at homeon purpose mama hippie uh, they
were my parents.
By the way, caleb has long hair.
David (02:54):
I would say nipple length , and he's got a good, some good
facial hair, but nicelymanicured.
He's not, doesn't look homeless.
Really.
You do have something going onwith your eyes which is
interesting.
Caleb (03:06):
Oh, vitiligo I have vitiligo facts that is that when
I was 14.
It's a harmless autoimmunedisorder where your body, your
immune system, destroys yourmelanocytes so you have patches
of your skin with no pigment.
Oh uh, michael jackson claimedto have had this disease but was
probably just like early on thekorean skincare trend of skin
lightening, sure, uh.
(03:26):
So we don't vitiligo people.
I I speak for us all when I sayI'm not sure that that was who
we would have picked for ourspokesperson, but that's who we
have as a point of recognition.
David (03:36):
Yeah, yeah, I've a bit on the hands and then on the eye
everywhere, oh everywhere.
Caleb (03:42):
That's exciting, ladies.
David (03:46):
No, no, but it looks just as a a first impression, it
looks like you have sixsunglasses that you're just like
rocking that's.
Caleb (03:54):
That's my favorite uh interpretation of what it might
be on on site, because I I dofear I get insecure, that people
will think that I'm tanninglike I'm just laying in a.
David (04:06):
Well, you just had a disastrous tanning bed session
where, like this is a spray tancatastrophe.
Caleb (04:11):
That happens I don't want people to think I'm no vain
enough to go, not not to allright, I derail, but that's cool
.
David (04:19):
no, it looks cool.
I think it's a good look, soanyway, it's in fashion for sure
.
You have witnessed how manyopen mic performances estimate
Back of the napkin.
Holy crap.
Years and numbers.
Caleb (04:34):
We got to do some maths.
Yeah, because let's see I'llspeed this part up, bro, take
your time.
Four or five open mics a week?
For how many weeks?
Let's say an average of fourmics a week.
For how many weeks?
David (04:46):
let's say an average of four mics.
Caleb (04:47):
Okay, a week with an average of, let's say, 12 people
on them.
David (04:53):
Okay, 12 that's 48, jesus christ.
That's a lot of hours.
That's 48 a week.
Sounds like you've been goingto six years of open mics.
It's a lot.
At 50 weeks a year, obviouslyyou're not going to every week.
So I would say you're somewherebetween 200 and 250 times 42
weeks.
(05:13):
Wow, wow, wow.
So let's just call it lowparameter.
Caleb (05:18):
We'll go 200 times 42 which is 8,000, that's a lot
never thought about it that way.
David (05:29):
Yeah, wow, wow, wow 200 times 4 is 800, so 200 times 40
is 8,000.
Ok, I just wanted to you're inthe top .001% of the global
population in open micwitnessing and I would say maybe
top 100 on earth.
Caleb (05:50):
There's thousands of us.
David (05:51):
Dude, I think you're number one in the world Number
one.
No, but so.
So this is an incredibleinsight.
And I think when you mentionedwhen we, when we had this idea
to come on, I had just done anopen mic I think it was my 18th
or 19th ever and then we juststarted chatting and I was like
(06:13):
I fucking hate open mics and youwere like I love open mics.
And I was like yeah, and so Iwas like, oh, this is going to
be great.
So it's like Crossfire on CNNright now.
Caleb (06:24):
Okay, no, no, we don't have to argue about it, but I
would love to know why?
David (06:27):
what did it?
What is it about open mics thatyou love?
Yeah, what have you learnedwatching open mics?
You know, I'm just gonna, I'mjust, I just want to extract
your experience and especiallyfor listeners, because there's
it's a ton of value forversioning stand-ups and just
people who are who are nowinterested in the whole world of
stand-up comedy yeah, what do Ilove about open mics?
Caleb (06:48):
oh, the humanity of it all.
Yeah, um, if you're a hardcorecomedy fan, you like I think
even through, uh, someone's likenervous jitters because it's
their first couple of mics cansee a good premise and a good
joke.
I love that.
(07:08):
I love to see people facingtheir fears right.
People who, um, do it one time,like these, these people that
come in with all sorts ofbravado, who you don't expect to
just crumble as soon as theyget up there.
That's great too.
That's a part of it.
Yeah, uh, this shot in freud alittle bit of it but also just
(07:31):
the the vulnerability of it
David (07:33):
be like yeah, big tough guy like this is hard and that's
okay and we support you anyway,man sweet, you're much more of
a sweetheart than I thought.
Now I feel like a real asshole.
No, not at all.
Caleb (07:43):
No, go, keep going uh and I love uh.
Also like people getting theirfirst laughs, like seeing people
light up.
They're getting their firstlaughs.
Um, I love uh watching thedownfall of uh, the itinerant
alcoholic piece of shit that youwish wasn't as funny as he is
(08:09):
and over time gets less funnyand less coherent.
That's a, that's a perfect openmic experience over the course
of years.
David (08:18):
You mean so he comes his first guy up.
There's all this like promise.
Caleb (08:23):
Right, and then his alcoholism.
The potential there's so muchpotential and he goes the other
way and then you realize thattwo years in he hasn't written
10 minutes.
And uh is doing and doing crowdwork at an open mic.
That is increased.
It's just devolving, yeah, weekover week.
(08:44):
Yeah, there's all that.
Um, that's a valuable lessontoo um it's all, it's all
learning.
Right, I love that?
Um, I definitely.
I think earlier we we assertedthat maybe I had some sort of
natural inclination to be funny,but I didn't recognize it and I
think that I would say, towhatever degree I've improved in
(09:06):
my stand-up, writing, delivery,performance, doing stand-up,
especially at open mics, I hadto learn it.
I'm a student of it.
None of it came naturally to meyeah, and I was as insufferable
as a lot of other open micersare when they start doing, you
know, hack shit, doing dirty,gross stuff for the sake of
(09:35):
being perverse and shocking.
And I still revel in that tosome degree.
I mean, like I've featured nowfor like national headliners at
Empire Comedy Club.
I've had the blessing to beable to do that and like my A
material I always pull out isabout putting an ice cream scoop
in my ass.
You know like I think that'sfine.
David (09:51):
It's true, it's the true story.
Caleb (09:55):
So, but that all came out of open mics and that culture
of the open mic.
David (10:04):
So where are you at in your career?
I'm gonna just, I just want tosort of oh, let's start there.
Where am I?
I mean, how many?
So?
So you started when?
What year?
2016?
Okay, and then you took acouple years off during covid
yeah, uh, I.
Caleb (10:19):
So I was, like in 2018, a semi-finalist at the Empire
Comedy Competition and like, dida half hour because that was
the prize for the semi-finalist.
David (10:31):
You had a half hour materials two years in.
Caleb (10:35):
I didn't, but I certainly performed for 30 minutes.
I did my time.
David (10:40):
That's amazing, that's terrifying.
Caleb (10:42):
It wasn't great.
Looking back on it it couldhave been a lot worse like, but
I was dedicated to going to themics and I would write a new
five minutes every week for myfirst couple of years whoa yeah
and no matter if it and a lot ofit.
You know ate shit, of course,but you never retested material,
never until I started gettingon shows in 2018, I would do a
(11:05):
new thing every week.
Okay, but hold on a second.
David (11:08):
How do you know that it's funny or not?
Because this is my big problemwith open mics Like, for example
, the one we just were attogether.
Those were all ostensibly otherstand-ups.
I was looking at the audienceas people were being you know it
wasn't bad some of the stufflooking at the audience as
people were being.
You know they were it wasn'tbad.
Some of the stuff, yeah, and noone's paying attention dude
(11:28):
everyone's like looking at theirown notes, so how on?
Earth?
Do you know that a joke is goodor not?
you don't not based on one's uhopen mic performance for sure so
do you wish you tried more ofthose out, or were you like the
pipe metaphor where you're just,I need two years of unclogging
my shit pipe I did need that Ithink, I did.
Caleb (11:48):
I think it was an outlet for me.
I think I also had no ambitionum, beyond getting better at
public speaking, right likebeing a little less nervous
every week, and, uh, the onlyagenda I had was to like say my
ideas out loud to a room yeah uh, for those for that time.
So it was a lot.
It was like an outlet thing andyeah, I was just writing uh and
(12:12):
like, uh, getting it out, but,amazing dude, once I started to
get shows, uh, then it's likewell, I would like them to laugh
.
Yeah, the open micers, I didn'treally.
I did care a little bit.
I wanted to like get into thosecircles and I wanted that.
(12:36):
I did want them to laugh, but Iwas more preoccupied with like
writing little rants.
David (12:42):
Yeah, I'm very ranty.
I was rant, ranty too and Ithought that was enough.
Caleb (12:47):
Yeah and no, we can't all be bill burr, but, um, you
don't.
And comics are not an audiencethat paid to come to a comedy
show either, so it's not doingyou any service.
Uh, you can glean plenty ofuseful information right from
(13:07):
just the performance, the, the Iwould say 80 of the utility of
going to an open mic for thefirst lot of time that you're
going to open mics is justcomfort, getting comfortable on
stage.
Yes, speaking, hitting thepoints you wanted to hit in a
bit.
That's like a huge chunk of theusefulness.
It's not about identifyingwhat's funny, and I would also
(13:30):
say uh, my, my point of view onit is I do, I do know that
something is funny when I writeit and it it's more dependent on
me successfully saying it,delivering it, than it is the,
the word.
Like I know, like you know, youcan identify a joke, you know
(13:52):
what the laugh line is right andand it might be not as funny as
you thought or it might befunnier than you thought, but
it's funny.
You know that when you write it.
David (14:05):
Well, it's like, you know it's a joke, you know that
there's a rhythm, that you havereleased the tension, and either
there's a laugh or not, but youhave stated a joke and if
you've done it with courage, youhave stuck it yeah and then
you're there to see, yeah, whatthe reaction is we.
Caleb (14:25):
I don't know if we were recording, but I was talking
about how I used to canvas andask people for money at the door
and when I was training collegekids to ask for money door to
door in our practice I would belike, how did you feel about
that ask when they would?
David (14:41):
get to the ask right.
Caleb (14:42):
Did you feel like it was a good ask?
Very similar, I feel like yes,you just know, I fucked that
joke up the joke is funny, but Ifucked it up or I nailed it.
Didn't get the laugh that Ithought it would.
Now we have to think what otherfactors went into why this room
of people in this context todaylooking at me, laughed only
(15:05):
this much at this thing.
That I think should be like thefinale to this big five minute
set or whatever you know, um,but you can't judge.
David (15:14):
Again, back to those open mics.
You can't judge the lack oflaughter on anything, that's
true, because no one's payingattention unless some people are
.
And like I've noticed as I'vegotten, I've progressed and
gotten objectively more, youknow, uh, playing by the rules
(15:35):
of stand-up and like sayingactual jokes, right, I?
I now see that some people arelike, you know, you hear a
couple and that's why therecording I you know gary
goldman's 366 tips, yeah, thatwe talked about.
Yeah, the number one is recordyour things and listen back.
And my friend al madrigo's donehbo specials.
He's like, he's like record andlisten where the laughs are and
(16:00):
where you're not getting alaugh.
That isn't importantinformation.
It's just gone.
Cut it, cut it.
I have the book Stephen King'sOn Writing, book that we were
both praising Same thing.
It's just like get rid of allextraneous everything, and that
seems to be a lot of the game.
It's more almost science, it'smore like tinkering in an
(16:21):
automobile shop.
Caleb (16:23):
Something that I recall from stephen king's own writing
is he describes it as likearchaeology like just brushing
with a toothbrush, uh-huh offthe stuff, right, revealing
exactly the structure of thething that's already there.
It's like a subtractivesculpture art, right.
(16:44):
Like you, it deforms.
In there, you got to chisel it,right yeah uh, and if you
chisel too much, you have adeformed thing.
If you if you don't chiselenough, you don't have a formed
thing at all.
David (16:54):
Yes, yeah, totally okay, so, so all right, I'm buying the
open mic.
The value of it, yeah, uh, and,and you're and totally about
getting comfortable.
I think, um, at my stage Idon't have the confidence you
have that the the joke is funny,meaning I can think it's funny
(17:15):
you know, but if it's, if itbombs, it bombs.
I know in talking ad nauseumwith so many people in the last
year, like sam morrell, who's sogood and so funny you talked to
sam morrell no, oh, he's sogood he's so good yeah whoever's
listening, go watch sam morrell.
Caleb (17:31):
But he was just in portland.
David (17:33):
Yeah, he was but I know that uh val over at the comedy
cellar sam his comedy sellershows is he's a writing machine
and he's, he's got, he's gotfive alts and he's like which
one val?
Which one should I go?
Which one did I?
Caleb (17:48):
go with, like what set, he should do.
David (17:50):
No, no, which joke he should do what's like, what's
funny like he's constantly andgary goldman's other tips is
just like the minute you have alaugh, like there's more laughs
in there.
We were talking about that.
There's more ways to you canprobably get three laughs where
you didn't think there was any.
You know and you can change aword whatever, but Val's
(18:12):
statement was Sam doesn't knowwhat's funny until he does it.
Caleb (18:17):
And he.
David (18:18):
I think let me preface it by saying I've witnessed people
testing jokes.
Caleb (18:26):
They're all funny.
David (18:28):
Yeah, I think what he's saying in his brain is what's
the funniest?
Caleb (18:32):
What's the one?
David (18:33):
Yeah, yeah, yes, and they don't know what the funniest is
.
They can think it is, but theyall know that they're jokes that
will get chuckles totally, yeah.
Caleb (18:42):
Yeah, that's the level, that's the only level of
confidence I have.
It's like this is not.
Nobody is going to throwsomething at me and tell me to
leave after I say this, you knowwhat I mean.
David (18:54):
Yeah, bare minimum.
They will see, they willappreciate the effort that went
into crafting a joke.
Caleb (18:59):
Quote unquote yeah, yeah yeah, I'm, and I'm by no means
like I would say samorelle,really brilliant joke writer I
don't know where thisdistinction lies in my brain
exactly, but like I don't thinkof myself as like a a great joke
writer, I'm, I, I am, I canwrite, I can articulate things
yeah, obviously to some degree.
(19:20):
Yeah like, but like it's notgonna be like 1970s joke book,
right formulaic that's done.
David (19:31):
That world is over.
Caleb (19:33):
But so I think like joke jokes a pretty nebulous, but I
don't think that I'm thestrongest joke writer.
I am a fucking weirdo.
And that goes a long way ifyou're able to bring people into
your point of view.
I'm much more interested inthat than I have endeavored to
(19:56):
nail the structural parts of it.
Not that I don't want thatchallenge too, um, and I do trim
some fat and think about whereto change words here and there,
but never been a great wordsmithme neither and I and I
constantly, when I wake up inthe morning I'm like what?
am I doing like I don't?
David (20:15):
because I have a friend who's a comedy writer
professional.
He's written scripts, he'swritten movies with ro De Niro,
like big comedy films, and Iwill reach out to him and I'll
usually record something in mycar or something.
And I'll be like what do youthink of this?
Does this feel hack?
And within like a nanosecondhe's got like three like it's
(20:37):
like blank.
That are just tight ass fuckingjokes.
Yeah, and I'm like is this your?
I'm gonna have him on thepodcast.
So I'm like is is your brainjust auto training joke.
It's like all day and he's likekind of yeah, I was like oh
yeah, because he's been in room.
He's been in sitcom rooms, youknow for that's his 8 000 you
(20:59):
know, thing of just likepitching jokes to 10 other good
comedy writers, yep, and so thatthat brain and I know that
that's not how my brain worksI'm more like with you,
philosophizing, thinking deeplyabout things.
My brain naturally goes toeither like fedex middle
management logistics, like howdo I get to my kid's school 20
(21:21):
seconds faster, or I'm just offin the clouds thinking of just
not jokes things I will say ifI'm writing every day I start to
get more of the downloads.
Caleb (21:35):
The accidental?
David (21:36):
oh that would be funny.
It's sort of like.
Caleb (21:38):
I have to keep my brain in that context do you feel,
when you're in that context,that sometimes they just appear
fully formed to you and there's,there's.
There's no wordsmithing,because you're just like well,
there it is.
I don't know where that camefrom rarely, but yes, it has
happened.
David (21:56):
And just like, yeah, that's what I want that yeah
because I'm I'm a lazy motherlike I want just to be
downloading constantly.
I know people.
Caleb (22:05):
Uh, I say this sometimes and I think that there's kind of
a worthy stigma surrounding it,like but?
But I think of comedy as like alow effort, high reward thing
really I do, yeah, which peoplehate?
I mean, I don't.
I haven't felt like going toall these open mics has been a
great effort, because I'menjoying it I genuinely enjoy it
(22:27):
, I love that's beautiful comedy, so it's not felt like but so I
have to pretend that that's thegrind.
David (22:34):
But I put in my reps uh-huh uh, but really like, I
just like writing, so I'll writesome crazy down, if I can get
laughs, that's how my friend,another comic, kevin christie,
who's been uh known forever andhe's a staple at the uh comedy
store in la and I'm like how doyou?
He goes up three times a week.
(22:55):
He has a, he has a neil brennanuh kind of mic, that that's all
for big stand-ups to test newmaterial.
And I was like how do you justkeep going?
He's like I don't know, I writeit and I'm like I need to see
if it's funny.
Caleb (23:10):
I just need to.
I relate to that Like yeah, areother people thinking this?
Or do they not realize they'rethinking this?
Or when I say this, are theygoing to think it's really funny
that I thought that.
Yeah, all that.
David (23:25):
I think I'm in the stage and I've said this on the
podcast but I think I'm in thestage where I'm trying to figure
out my life and story, almostlike in a memoir-esque way.
I'm like, how have I gottenhere?
Because I've kind of been a a Idon't know.
I just try to live in themoment, try to have fun, try to
do what's enjoyable, and then Ikind of wake up and I'm like I'm
(23:45):
46, I have a wife and kids, Ilive in maine.
Like how the fuck did thishappen?
Right and um, and so a lot ofthe writing that appeals to me
is kind of mining my personalexperience, which I know from
stand-up point of view.
Is there a?
I sense this, I don't know why.
Is there like a looking down onpeople who kind of like bring
(24:08):
their own personal life?
Is there like a snobbinessabout that that you are aware?
Caleb (24:16):
of.
Maybe what I think you might besensing is that low level open
micers are often really have ahard time being vulnerable, and
that they have always had humoras a deflective self-defense
mechanism.
And so what they?
(24:36):
When you talk about your life,they see it either as
self-absorption or vulnerabilitywhich terrifies them.
And they will then go to themechanism they've relied on
their whole lives, which is tohumiliate, not humiliate it.
(24:56):
What's the word?
What's the word?
They need to put it down yeahright, they need.
They need to be like oh this,you're talking about your kids.
Yeah, gay yeah, I mean yeahlike um, I don't know if it's
snobbery, I think it's actuallyjust a kind of neuroses that
(25:18):
they they can't take anythingseriously.
How unfunny would it be to likethink you know?
This, I also think, is why,like the people, the, the rare
comedians who like able to dodeep social commentary and like
have a point, are people thatare really really friggin funny
but are not debilitated by theirfunniness you know what I?
(25:40):
mean like uh, you'll meet peopleyou probably know, comedians
who can't turn it off never turnit off it's annoying and it's
annoying, it's like a it's it'skind of tragic yeah, it's like
you'll, you'll, they're justbidding all the time all bits
all the time and you can't evenhave a conversation with them or
(26:01):
like shit will be going on intheir life and you are trying
for just a moment to check inwith them as a friend and
they're like mom died, whatever,dude, it's not no, big deal
like and you're, that's actuallytragic.
So yeah, I don't, I don't know,I can't speak to like broader
comedy community outside of theone that I've experienced, but I
(26:22):
have noticed that that happensin the main comedy scene.
There are a lot of comics whoare just not able to get
vulnerable with you yeah, somaybe that's what you're sensing
yeah I've done a lot of likemining of my personal experience
too.
You don't see it as much.
I mean, we're all coming fromour own point of view.
(26:42):
It's all autobiography, yeah.
So if you're doing itintentionally, I think you
probably have a.
David (26:50):
You're a little head up on the folks that are doing it
unintentionally well, it's agood segue because I want to
talk about this idea of in ourcars we're like amazing and we
rip and like I've had rehearsalslike a half hour before an open
mic where I'm like ooh, fuck,yeah, it's going to crush, let's
(27:13):
go, baby, of course.
And then you get in this roomand the energy of the room and
you're like nothing I did in mycar will work, because the
energy is totally unmatched tothis.
Somehow I have to take theenergy, transmute it, transform
it into something where now myset works.
Can you speak to this idea oftaking control of a room or
(27:43):
being having to match your setto something in ineffable,
almost in a room?
Yeah, what, what do you knowabout that and what, how do you
see it and how do you deal with?
Caleb (27:56):
it.
Wow, yeah, no, that's a big.
I mean in the vacuum of yourcar you were all crushing.
If we could, if, if we couldall be who we are alone in our
car, we would all be stand-upcomics professional.
Yeah, if we could do that infront of people, that would be
(28:17):
pretty wild, I don't.
It's an interesting way to frameit that you that you framed it
like is it that you need to takecommand of the room and then
transmute the energy, or do youneed to meet the energy where
it's at?
And I think that's like a great, that's a great frame.
It's probably something likeboth at once.
Like I think maybe takingtaking command of a room
(28:40):
involves just instantlydemonstrating in your body
language, your countenance, yourcadence, immediately your
cadence, that you are likeyou're a part of the room.
You recognize the energy that'sin the room and you're
consciously bringing it to whereyou want it to go.
(29:00):
For a moment you have the micright, like what that it is.
That feels ineffable to me toto really describe how people
can do it.
You witness it, you recognizeit when you see it, but you're
but it's.
You know it would take, I think, a bunch of analysts could talk
about.
Oh, the body language and theirtone, or like, I have a deep
(29:22):
voice, or like, like, what is itthat is commanding the the
attention of the room?
I would stop just short ofsaying it's magic, right.
Cause there's definitely thingquantifiable things that we
could like appreciate about howit transpires that someone just
can go up there and in a roomthat was could appreciate.
About how it transpires thatsomeone just can go up there and
in a room that was gigglingabout stupid puns a moment ago,
(29:47):
talk about some serious topic,and get huge, crushing waves of
laughter from a room, just toreally quickly take control of
the room.
In that way, we are trying tomake people laugh, make them,
make them, making them do it.
Uh, it is an involuntaryresponse laughter right, so like
(30:10):
um I don't know.
David (30:13):
Yeah, that's such a cool answer.
I think it made me think of theadvice or that I've read, or
whatever, that you know there'scertain techniques, right, like
the person before, if you'vebeen listening, usually there's
a way to tie your first joke towhat they've done.
Yeah, uh, gary goldman's advicewas usually, I find it very
effective to get up there andmake an observation about the
(30:37):
either the room or the the stageor something that no one stated
.
That is honest and funny.
Yeah, and and I will say thatthe blink moment it's blink
moments when you see aprofessional get up there
because they are exuding likeyou're in safe hands and it
(30:58):
usually is immediately they finda way to make everyone laugh
and they're just like oh okay,this guy is funny and he's
comfortable and he's poised andthis is a professional.
Now I can relax and I think if Ihad to state what is the value
(31:21):
of open mic land?
It's getting good at that.
It's just going into hostileenvironments and being like I'm
gonna learn how to in 10 to 15seconds, 20, 30 max.
Yeah, just have everyone on myside yeah, well said.
Caleb (31:39):
That is a great insight on the value of open mic, I
think.
That is one of the definitetakeaways over time that you get
is that it's interestingbecause I see a lot of the
national headliners that comethrough Empire Comedy Club.
David (31:57):
Yeah, just for people listening, Caleb works at the
Empire Comedy Club, which is theone real comedy club in.
Just for people listening.
Uh, caleb is works at theempire comedy club, which is the
one real comedy club inportland, maine.
Yeah, and you guys get bigpeople yeah, huge names huge
names come through punching wayabove our weight class.
Caleb (32:11):
I would say for a 130 seat little club to have like
joe List annually come through.
I have had Big Jay Ogerson dolike four sold out shows
Incredible.
David (32:27):
Who is the guy that you took me?
Caleb (32:29):
Kyle Canaan yeah, awesome , we're going to have Doug
Stanhope in October, I think.
Just yeah, awesome.
Legends Ari Shafir we hadReally cool, really cool club.
Wow, I got derailed.
What was I going to say?
Oh, just that, those folks,those heavy hitters, there's a
(32:50):
certain degree to which theystill do that because it's like
a reflex to them.
I think at that point, whenyou're a pro to riff on the room
in in some way, to do likeyou're saying, uh, in the first
10 or 15 seconds, just make sureeveryone's like, yep, we're in
good hands, this is a prothere's a degree to which they
have less of an impetus to do itat all because they're them
(33:14):
just being the ticket that youbought yeah it already kind of
did that for him yeah I see thisespecially with, like lucas
zelnick, rachel uh, I almostsaid rachel rachel scanlon, uh,
people who have big onlinefollowings, who are there for
them.
That are their fans, who watchtheir content, their podcast,
(33:36):
their clips, their crowd work.
They are so excited to be inthe room with them.
That it's immediate, it's justimmediate.
Whatever the first thing out oftheir mouth is, it's gonna get
applause.
David (33:50):
You know that's sort of the world of the netflix special
, it's like yeah, you know whatI mean.
Like all those high ticket,those people love this comic.
Caleb (33:59):
Yeah, they're like bitter open micers who have no right
speculating.
We'll often be like at thatlevel.
How do you even know if it'sfunny?
They're just laughing becauseyou're Tom Segura.
It's like okay, dude.
David (34:13):
Sure yeah, keep telling yourself that.
Caleb (34:16):
Yeah, no, it's fun, it's a wow.
Yeah, that's a really great one.
I'm gonna tell noobs that aboutopen mics.
It's like getting comfortableon stage is the value of it and
learning how to uh bring theenergy of the room where you
wanted to go and like littlethings like that.
You also pick up from hostingshows yeah, there's a lot of
(34:39):
value to hosting, isn't there?
I've hosted a ton of shows andthat was something I had to.
To learn was like what?
I have to change my opening bit.
I have to do the kind of calland response like, oh, come on,
guys, we can do better than that, or something to that degree.
I have to ask them aren't youguys excited?
You know I have to uh, freaking, project my voice a little more
(35:03):
and like yell yeah um, that allis valuable.
Or just like the economy ofwords, like to to get through
house rules, even like if youfucking fumbled the house rules
and then five minutes later youget on stage to host.
They're already like who's thisfucking guy?
David (35:25):
yes, I have.
I'm trying to figure out a way,because when I speak there's
certain moods and you know whenyour brain's cooking that you're
you know more, more articulate,and then there are times where
you're, you know, tired orwhatever, and like I am now,
like it's like halting and youdon't really know what you're
saying.
There are certain comics likewoody allen comes to mind other
(35:49):
where, like almost the whole the, the, that thing becomes the
part of the act yeah and there'sa part of me that's like I
think I'm gonna have to do thatbecause totally I can't be
crispy cream.
You know what I mean?
I I could just yeah I don'thave that and I, when I listen
back to my sets, like I'm thefiller words, I'm like dude,
(36:10):
what are you doing?
Like the amount of filler words, and sometimes not yeah and I'm
just like shit.
Caleb (36:16):
Like because the filler words deflate and I think they
show amateurism and you'relosing trust if you're going uh
uh, At the very least you'rethinking about the next word
you're going to say that goesaway just from repetitions to a
certain degree.
David (36:35):
Yeah, and there's stories I've told maybe 10 times where
I know the story and I canchange a little bit.
And that's a lot of what it isright that fluidity is good.
Caleb (36:44):
there's also the other side of that coin where, uh,
you've told that you're tellingthe joke for the 50th time and
it comes off too polished, right?
So, um, like, really, reallystrong joke writers I think have
to will intentionally include afiller word.
Yes, I have a bunch of bitswhere part of it is that it's
(37:08):
like oh, I'm, what was I goingto say?
Oh right, the punchline.
David (37:12):
Like I knew exactly what I was going to say.
Caleb (37:15):
Knew it right yeah, so it is.
I've noticed.
So when I was I don't know whyI keep coming back to this it
was valuable for my stand-upwhen I was canvassing, knocking
door to door.
I was training people to dothis political, political
donations.
David (37:30):
Right, talking about my version of stuff yeah, it's not.
Caleb (37:34):
You know, nobody wants you interrupting their dinner
time and and it's hell.
But one of the things that Isaw was completely unhelpful in
training people how to canvaswas pointing out filler words.
It would just completelydestroy the confidence.
David (37:52):
Yeah, because they would say one and then they'd panic.
Caleb (37:54):
Yes, so it was like not the feedback that a lot of
people needed to hear, that, um,I wouldn't, I wouldn't worry
too much it's so funny.
David (38:03):
You say that because I remember my third open mic or
something, and you may have beenthere.
It was at empire and I it wasmy first time, maybe, at empire
and I was like, oh, my first two, there were so many uhs, it was
so messy, I gotta be chris,like the pros, and I went and it
was like this robotic,perfectly stated thing that was
(38:24):
just not.
Not a single laugh, you know,like just like just crickets for
five minutes, dude, yeah, and Iremember being like, okay, I
guess crispy isn't the wholeRight, you know, so, so, and now
, yeah, the, the, the wholething.
One of the guys that I reallylike, uh, his name's Fox Uh, I'm
(38:51):
spacing his first name, buthe's, he's an LA really good
writer.
And Kirk Fox, uh, if you'venever heard of him, you should
check it out.
Go to his Instagram.
Caleb (38:59):
Yeah, and Kirk Fox.
If you've never heard of him,you should check it out.
Go to his.
David (39:01):
Instagram.
Yeah, really funny and he's gota really good reputation.
He started late, like hestarted he was a tennis pro and
then he started in his mid 40sand now like is big with all the
big hitters.
He had DM'd me because we havemutual friends and he was like
I'll help you write some jokes.
And I was like I got to learnhow to write a joke for us
(39:21):
before I started pulling likesuper pros, you know.
Caleb (39:24):
Sure.
David (39:24):
But he said um, he said just talk it's, it's like it's
just talking with people asopposed to at them, and that was
like the only thing he said andand that you know, it's like
this simple thing that you'relike, that's like a nothing
(39:44):
statement, right, right, talk atthem.
Well, of course I'm talkingwith them, but there's something
there that's very deep and I'venoticed in all my open mics.
If I go up and I have some setin my head and I just like to
get through it properly, it it'snot nearly as good or as
satisfying as being messy, but Ifeel like I'm like dude, we're
(40:07):
talking and we're having a we'rehaving a little chat ski right,
you want to guys have a littlechat ski with me up here you
know, like that kind of thing,and you can say it, you know.
And then then you feel likeafter our interview to like I'm
gonna have being a great movebecause I've connected with you
in a very real way yeah and thenthe point is like you can do
that on stage, yeah, and anytimeI I just go up with the
(40:29):
intention to connect.
There's just more goodwillcoming my way, you know totally.
Caleb (40:34):
Um and that'll also change what you want to write
about, because, uh, if you'rewriting autobiographically, it's
like well, we got to talk abouthow this is like the human
experience, not just myautobiography, right, but like
what's funny about this thateveryone can talk about, or, or
if you're doing, or you're atleast more self-aware to be like
(40:56):
that was just just this is ajust me experience, right, y'all
like in the room.
And then there's also a thingthere, uh, which I've heard like
comedy teacher types talk about, where you're like training
them that their input is a partof it.
Uh will encourage the laughterand reactions.
Who's Oz?
If you're having a dialoguewith uh, you're asking them, you
(41:20):
hear it Standups do this allthe time, even if it's
completely rhetorical, is like,right, like yeah, what.
Nodding with folks just toconnect that connection as
opposed to just reciting at them.
David (41:33):
Yeah.
Caleb (41:34):
Uh, reading lines to them .
David (41:36):
Yeah, I would say, the premise setting up is always in
the sort of you language, likeyou know, when you blank.
Caleb (41:48):
Now I just I want to write a five minute set where I
only say when one goes to thepost office, when one, when one,
no, you, yeah, so I'm going to,because we're I'm going to be
nearing my children's schoolpickup, so I do have to.
David (42:07):
Kind of I could talk for another couple hours.
Hell, yeah, if I may, I thinkpeople would be interested.
You've witnessed.
Did you watch my set onThursday?
Yeah, it was about meditation.
Yeah, like just you know thepremise is, I've done so much
(42:30):
meditation to try to become abetter person.
All I'm doing is becoming moremindful of what a degenerate I
am.
And then you know variousthings.
I would be very grateful if youjust either, maybe in the
context of, like, what are younoticing that I'm doing?
Well, what do you?
What are you noticing that Ishould work on?
(42:52):
And what are you noticing Like,is there any raw?
Is there anything that you knowhit you as like a I don't know,
kind of a, an area that isworth mining, if you will.
And I don't want to put you onthe spot because you may not
even remember what I said oranything I did.
Caleb (43:12):
But any kind of impression.
I've always had positiveimpressions of your sets.
I feel like I'm not usuallydigesting people's sets in a in
a way of like oh how can I givethem tips, right?
Yeah um, nor am I super, supercritical if you, if you're doing
(43:35):
so, what maybe?
Maybe the feedback then is Ithink you're doing a lot of the
fundamental stuff right, whichis just that you're, and maybe
this is learned.
I remember your MillennialsNeed to Fuck More.
First, open mic, hot take asbeing really funny and it going
well.
David (43:52):
Oh, interesting.
Caleb (43:53):
I don't remember any crickets sets from you, but I
haven't been at every single one.
David (43:58):
You haven't been at every one.
Caleb (43:59):
No, the first yeah, I would say you're doing a lot of
the fundamental things right,and maybe just from this
conversation too, I would say,if you've got a premise that's
that loose, it feels like you'reopening yourself up to the
possibility that when you get upthere, what you wrote down
isn't what you're going to sayand that that kind of
(44:21):
playfulness can go a long wayand create more connections and
have a more conversational uhfeeling, which can be really,
really fun for people with,where you still have a few punch
lines in your back pocket todeploy, if the right energy and
moment appears in, in justbringing the topic up with
(44:44):
people, like if the premise is.
I've done all this meditatingand now I'm just more aware of
what a degenerate I am.
I've done a lot of open micsets with nothing more than a
premise.
People sometimes would callthat like writing on stage.
I don't know to what degree Ido that, but sometimes my only
goal for an open mic set is tosay it out loud in front of
(45:06):
people in a room, see whatreactions just the premise
starts to bring and go fromthere.
David (45:13):
Do you start doing crowd work a little bit?
Caleb (45:16):
after I will occasionally .
I don't know how useful thatalways is for writing, but I
guess what I'm saying is likeoccasionally, I don't know how
useful that always is forwriting, but I guess what I'm
saying is like how comfortableare you with, like the
extemporaneous?
Writing yeah based on a premise, because I think that you would
really thrive in that, and thenyou come away with something
that you could do lessimprovisationally later oh, this
(45:39):
is beautiful because I that's areally cool idea.
David (45:44):
It's ballsy and I I think I it's ballsy in the sense that
you're kind of like I don'tknow what I'm gonna say yeah,
but it's low stakes it's superlow, you know I think my
challenge is because I'mrecording them all and I think
it the the premise of thispodcast was that I share them
all.
It feels weirdly high stakesevery single one but I don't
have to share and I've stoppedsharing every open mic.
Caleb (46:07):
I do, but you don't need to go like full.
David (46:10):
hey, let's workshop this premise together, guys, yeah,
yeah, yeah.
Caleb (46:13):
But you don't always need to know the punchline.
If you mull over the premiseand what you think is funny
about it, you can, I think.
David (46:23):
I don't know, that might be horrible advice, but no, no,
I don't think it is, becauseultimately I get my enjoyment
and I try to north star, likewhat is exciting about this for
me?
Yeah, and I think one of mygreat challenges is is repeating
jokes.
I don't like doing it in life.
I mean there's a couple thatyou do because it's almost like
a parody of the joke.
Yep, you know, like one of myfriends has a line where where
(46:48):
his pickup line, oh no, he'll bewith a group of his buddies and
and there'll be a table ofgirls like with an earshot and
he'll be like guys, guys, enoughwith the fucking donkey dick
jokes.
It's old, you know, so they canhear and like that dumb shit.
Like I could hear it 50 timesand still find it you know, um.
(47:12):
So there's certain jokes which Iwon't tire of saying, I would
say on stage, but for the mostpart there's a sort of a almost
like a shame that I'm doing thesame thing.
And that's a problem withstandup, I think, because you
are all constantly tinkering anddoing the same thing.
Caleb (47:30):
One of the things.
David (47:30):
That's hard.
While you think about aresponse, is that I that that
gave me a bad feeling waswatching Louis CK do this
amazing set and his performancesare so good because they're so
coming out of his head likethere's such a.
I'm talking with you and thisis just coming out of my mouth
(47:51):
for the first time and then thisdamn instagram person put on
another night the same exactthing and it was like exactly,
yeah the same.
Caleb (48:01):
He's master of that.
David (48:02):
He's a master, it's every nano beat is mapped out oh yeah
and I was like, oh shit, like Iwonder if that's obviously he
enjoys, that, he obviously has aprofound love.
I want to.
I I worry that I won't havethat love and I have another
friend who started stand-up.
He's like really famous daxshepherd and he he started uh
(48:24):
doing he.
When I said I was going to dothis project, he was like I did
stand-up actually right when mykids were born and he was like I
challenged myself.
I just do new stories everynight and he got hooked in Vegas
, but he never repeated it rightand we sort of have a he's a
master improviser, sure, uh.
But anyway, my, my that'sreally my long-winded way of
(48:44):
saying there's concern I havegoing to bed at night.
That, like stand-up, is anamazing art form that I'm
clearly intrigued by, but I'mjust like, oh shit, like yeah,
is it?
Is it going to be enjoyable toto?
Keep repeating to to have sometight 10.
That I repeat 30 times yeah, I.
Caleb (49:06):
So I'm only recently beginning to struggle with this
because it's been.
I have like I've got this like20 minutes.
I have like that.
I do the same way every timeand I've started to get sick of
some of them.
I hate all of those jokes nowto some degree, but I, I would,
(49:26):
my, I don't know, I would see mysuggestion would be like that.
This, uh, stand-up versus improvdichotomy is a false one, and
both muscles are reallyimportant to to exercise and
that you, like I said I did anew five minutes for like every
week, multiple open micssometimes for like two years.
(49:49):
I was not interested inrepeating stuff.
That's wild, and I had the samesort of fear too.
It was like, well, that's notgonna be fun, like I said the
thing and I don't need to goback there.
But there is a ton of value, ofcourse.
That is.
The stand-up game is in thetweaking and the wordsmithing
(50:11):
and then performing it as thoughit's the first time you've ever
said it every single time.
There is a lot of value in that, but there's still, I think,
because of that energy in roomswhere we keep talking about,
there's a ton of value in theimprovisational stuff as well,
and like you don't need tobecome a crowd work guy to mine
(50:38):
the value from whatever you canget out of that, right, I would
say.
So I think, think you, and alsoI mean you've done how long
have you been doing this nowlike, well, I did my first open
mic about a year ago, but I'mstill below.
David (50:54):
I'm nearing the first 20 open mics yeah, yeah, that
you're.
Caleb (50:59):
You're your first 105 minutes that you write aren't
going to be the ones that youwant to like, immortalize, yeah,
you know, don't be so sure,yeah I, I think I'm almost done.
David (51:14):
I think my life's work's almost complete so I start
commissioning the equestrianstatues well, I, exactly, I, uh,
no, I.
I was down at the bitterfordopen mic, uh, mulligans or
whatever, and and it was thefirst time I had a real set,
that was like I, I reallyfocused on the writing and and
(51:37):
then all those guys asked me tocome do like the real you know
set or whatever where there'spaying customers yeah which was
which was a really cool feelingof, uh, validation of the hard
work that I felt like I had done.
That being said, they're like soyou got 10 minutes right and I
was like what?
So now it's sort of like okay,I had this thing that was
(52:00):
probably took six minutes toperform, but if I do it right,
it's probably four minutes orthree and a half, yep, and now I
need another seven to kind ofbe that minimum.
Would you say.
10 minutes is kind of theminimum where you can start
being asked to to join shows uh,no, we'll do guest spots that
are five on some showcases yeah.
Caleb (52:20):
Yeah For, like much newer people, people who want to see
how they handle it.
Yeah, 10 feels really short tome now.
Yeah, but it isn't.
It's so much time you can do somuch.
Yeah, just watch the first fiveminutes of any of your favorite
specials.
There's so much.
David (52:38):
There's so much packed in .
That's what my friend Kevinsays.
Caleb (52:48):
He so much packed in and that's my friend kevin's day,
he's just like, at the end ofthe day it's last minute.
Yeah, you know, and you're like, oh, and those guys, that's
what they're doing.
This is another great thing Ihad early on was that at bull
phoenix in portland when thereused to be comedy upstairs run
by this awesome guy, mike mikelevinsky, I think his name a
really cool guy he would do atthe end of their showcases,
anybody in the audience whowanted to could take the one
minute challenge and he wouldgive a dollar to whoever had the
(53:08):
best one minute.
That's fun, I think.
Starting to think about minutesof comedy, because one time I
was like I'm going to win theone minute thing and I went
there and this awesome comic inPortland, amelia, that I love,
just showed up out of the blueand everyone was like, oh my god
, amelia is making an appearancelike we haven't seen her in
(53:30):
months because she kind of comesin and out, she's got a busy
life, uh, and she just crushedme oh based on like telling just
a story from her day.
Like casually, I was like fuck,I wrote six ten second jokes for
this and it was really reallygood lesson and I have a file on
(53:52):
my phone to this day that isjust one minute challenges where
I'm thinking in terms of laughsper minute.
I'm not a one-liner guy.
I don't.
I don't even think of myself asa great joke writer, but it's.
It is important to think aboutit minute by minute.
And even if it's a, I'mnotorious among the comics in
Portland that I work with a lotfor just making a thing way too
(54:14):
fucking long and just havinglike a seven-minute rant about
Amish people that I don't needto have.
So I constantly need to bethinking more, yeah, like what's
the tightest version of thisthat I don't need to have?
So I constantly need to bethinking more, yeah, like what's
the tightest version of this?
Where's the setup, where's thepunch in it?
And that's a really funexercise to do is just like give
yourself a one minute challengeand then write 10 of them and
(54:37):
then you'll be all set for yourcomedy mill gig.
David (54:40):
Nikki Glaser was on Howard Stern, yeah, and she just
explained one regret she had,which is that she didn't ask
friends to help her with hersets earlier, like she just did
it all alone and she thinks it'slike so much more fun.
I would have gone so muchbetter, so much faster.
Yeah, and that was all I needed, because I've been trying to
prove to myself that I could begood on my own and, like you
(55:00):
know, I want this all to be me.
It was like almost egoic andthen I started just saying fuck
it, reaching out, sending a rantto a friend what do you think
is this hack?
And just the joy and enjoymentand the just collaborating and
not being so precious, totally.
And the other thing my friendsays like dude, if you're in two
years and this is your, yourwalking testament if you're in
two years still performing thesejokes that you wrote in your
(55:24):
first year of stand-up, like youare failing dude, right, like
it, that is not the game.
And so I think, like you, youjust did it, naturally, without
that advice.
You just kind of had anintuitive sense like I just
gotta fucking get unclog thepipe.
Man, I, man, I did, yeah.
Caleb (55:41):
Yeah, and I've only recently become less precious
about like accepting tags frompeople.
David (55:48):
Only recently.
Caleb (55:50):
Yeah, so I totally agree with that.
It resonates that you're goingto have awesome people around
you who are very clever too, andyou're going to hopefully
you're like carpooling to somegig an hour and a half away.
You got all that time.
You're just riffing like stuff.
That's the best thing ever,that's if you can share even a
(56:12):
microsecond of that joy thathappens in a car, just driving
with another comic on stage likedon't deprive audiences of that
.
It probably was really fuckingfunny.
David (56:24):
Yeah, I think it would supercharge development to just
be around comics all the time,and I think those guys are you
know I think the top guys are.
That's their friends.
They're just constantly hangingwith them at the clubs.
Caleb (56:37):
Yeah, they talk about the good hang, the other part of
this work, the social networkingaspect of it, where it's like
you can be really really funnyand talented and, uh, absolute,
uh, displeasure to be around andthen you're not gonna get far
yeah, uh, that is something I'vehad to reckon with too.
(57:00):
Not that I'm like not fun to bearound, but I'm just like not
as motivated by companionship asI ought to be, and I've worked
on that.
David (57:08):
Are you a lone wolf?
Caleb (57:09):
Definitely like a homebody and just very isolating
, self-isolating.
Yeah, I've working at the.
Actually working at the clubhas helped with that a lot too.
It's like now these people arelike my coworkers.
I'm not going out to the micand sitting alone, I'm like
(57:30):
behind the bar.
There's like a customer facingaspect to it.
David (57:35):
That's four times a week, right?
Yeah, four.
Caleb (57:39):
Monday, yesterday went pretty well.
It might be five soon, but yeah, but it's been good for me.
I completely agree.
We all need to be bettercollaborators with one another
and just share in that, in thejoy of it.
We all have this shared joy forhumor and funny and the craft
like 100.
Yeah, nikki blazer said uh,she's.
David (58:01):
you don't blame an interior decorator for, like,
borrowing the tapestry or thefabric, and so she sees it more
as like you're a designer asopposed to like, and I thought
that was cool For her to saythat.
You know it felt from someonein her position.
(58:21):
It's probably more better forher career to be like.
No, this is like me, like yeah,there were writers at the
golden globes, but like that wasmy stuff, you know.
And she was just like no, um, soanyway, well, caleb theodore
sherman, thank you.
Where can people find you?
Your instagram is caleb thesherman at caleb the sherman
(58:45):
yeah and do you have any of yoursets on uh on the interweb?
Caleb (58:49):
I do have quite a few clips up on youtube.
David (58:53):
Uh yeah, on youtube as well, on instagram too oh,
instagram is the place to seesome of your stuff talk.
Caleb (59:00):
I went through phase I was throwing content up like
three times a week and veryquickly got discouraged by that.
But oh, it's awful the gramsthere, and you can know I'm
always at empire comedy club inportland, maine go say hi to
caleb at the empire comedy clubin portland.
David (59:17):
Yeah uh, he's tall, he's, he's handsome, he's fit, he's
what?
220 6'3 did you?
Caleb (59:24):
did you know that because I say that in one of my jokes,
or did you just?
No, I'm a weirdo I I just 6'5220 6'5, 220.
David (59:31):
Guess what big boy I am?
Caleb (59:33):
6'4 and a half, 230, dude taller than me I'm like a half
inch taller maybe I don't know,maybe you're 6'5, I'm 6'5, yeah,
you're tall, you're taller, Idon't know, I don't five.
David (59:43):
Yeah, you're tall.
You're taller.
I don't know.
I don't know it's all posture,but I, um I'm on an all sugar
diet and I'm just gaining rapidweight, so it's great.
Caleb (59:51):
How many large Papa John's pizzas do you eat per
week?
David (59:55):
Oh, no, no, pizza dude, I'm not allowed to eat that.
No, no, I can't eat.
Caleb (59:59):
I'm like I can't eat grains Averaging more than one
large pizza myself a week.
David (01:00:05):
Well, it's a nice price right, it's good value.
Calories per penny.
Caleb (01:00:10):
Yeah, yeah, yeah, 2,500 calories 2,500 calories.
David (01:00:14):
What is it?
You probably have a coupon.
It's like eight bucks, right.
Caleb (01:00:17):
Nine ten.
If you're loyal, you get a freemedium pizza from Domino's
every like 20 pies.
David (01:00:25):
Dude Dom loyal.
You get a free medium pizzafrom domino's every like 20 pies
do domino's I miss domino's.
Caleb (01:00:29):
What's your go-to pie?
Uh, in portland.
Well, papa john's, what's yourgo-to?
Pop it, oh, and pop just garlicstuffed crust with uh so
there's cheese in the crust?
David (01:00:36):
oh yeah, and it's garlic.
Sure, I think they mean theyclaim to have garlic night
terrors.
But and um, you can't eat grains, your uh well, sugar, no, no, I
, I yeah no, I, if people whoknow me well like I'm always
doing, uh, some sort of weirdthing to try to, you know, try
(01:00:57):
to feel better.
You know I can't do drugsanymore, so it's like you have
to feel better for what you eat.
Super fun, yeah, this was a lotof fun.
Yeah, so I'll be seeing you.
I'll see you at Empire man.
Hell.
Yeah, all right, brother, peace.
Well, I hope you enjoyed thatas much as I did.
(01:01:18):
I'm leaving a little Easter eggfor everybody, because I assume
Caleb's parents would probablylisten to most of this, but if
they're anything like my parents, they would tune out eight to
ten minutes in.
So I've left an Easter eggwhich they will regret not
hearing, because it's a secretthat Caleb revealed probably
about seven minutes into usgetting to know each other, and
(01:01:42):
I'm going to leave you with thiswonderful little clip.
One more thing I'll say aboutCaleb.
In re-listening to this episodeand getting it prepared for the
World Wide Web, his words seepinto my consciousness, and so I
found myself today, wednesday,writing new stuff for an open
(01:02:07):
mic, and because of the freedomwith which he explained his own
open mics, it inspired me.
Caleb inspired me to take somemore risks on stage and to not
be so hung up on being perfector looking professional.
Open mics are low stakes andthey are a place to push the
(01:02:30):
envelope and to explore If youcan be terrible for four minutes
and 58 seconds, but if there'sone nano moment where you
realize something, you discoversomething, then that time is
worth it.
I think that's what I'velearned on this from this
interview.
This isn't about becomingperfect.
(01:02:51):
This is about doing it your way, and there is only one place
left where you can trulyexperiment and do whatever the
fuck you want, and that's openmics.
So what am I saying?
I've gone from an open michater to someone who mildly
(01:03:15):
respects them.
No, I see a lot more of thevalue and I thank Caleb for that
.
Is there anything you've hiddenfrom your parents that you'd
like to reveal right now.
Caleb (01:03:25):
I've reveled in revealing those things to them over time
so much that there's almostnothing left there's one thing
that I do, that I do bit abouton stage all the time that still
hasn't made its way back tothem.
That is the last.
What is that bit the?
(01:03:45):
Uh, it involves butt stuff yeah, anal.
Yeah, okay, yep, and umreceiving or giving um, being a
teenager that was shoving randomcommon household objects in
their butt, in your own butt, inmy butt, at a boy, yeah, at a
boy, as one just exploring thebit is about.
David (01:04:02):
It's like a psa to parents, so that In your own
butt, in my butt, atta boy, yeah, atta boy, as one does, just
exploring the wonderland, thebit is about.
Caleb (01:04:05):
It's like a PSA to parents, so that hopefully they
go home from a comedy show andthey see everything in their
house in a new light Glistening,have some kind of a talk with
their kids.
David (01:04:17):
Harm reduction, I'm just doing a service.
Yeah, I was imagining yourparents hearing the bit and then
looking at all the householdobjects.
Caleb (01:04:26):
In particular, a specific ice cream scoop that I know is
still in their silverware drawer.
David (01:04:32):
Good Lord.
Caleb (01:04:33):
Yep, it's out there now.
That's fantastic.
David (01:04:35):
It is most certainly on the pod.
Yeah, it just makes me want towish everyone an incredible week
(01:04:56):
full of anal venery.
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