Conan O'Brien Stuns as Oscars Host - with guest Mike Chisholm from The Letterman Podcast - Daily Comedy News with Johnny Mac

Episode Transcript
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Speaker 1 (00:03):
Kalaroga Shark Media.

Speaker 2 (00:09):
Hiley hoo. I'm Johnny Mack with your daily comedy news
bonus edition. As promised, I pained Mike Chisholm from The
Letterman Podcast to get him on here, and I have
one question for Mike and then I'm gonna let him go. Mike,
are you prepared to admit to my fans, your fans,
Letterman fans, Conan fans, that Conan O'Brien is better at
hosting the Oscars than David Letterman.

Speaker 3 (00:28):
Man, not as only is he better at hosting than
David Letterman, I would say that he is better than
hosting than only the upper echelon of best hosts of
all time. Conan absolutely knocked it out of the park
last night. Oh my god, what a great Oscars that was.

Speaker 2 (00:47):
I love that you didn't hesitate at all, because we
all know we both love Dave. But it is what
it is. But yeah, Conan was fantastic. I see a
note here. This is from comedian Jeff Tweety. I just
saw this on threads. He wrote, Conan my be the
most beloved crossover comedian of the last thirty years. You
talk about a guy who crushes it with anti comedy,
comedy snobs, yep and traditional club stand up fans. Has

(01:09):
no real controversies except ones where he's screwed over by
Jay Leno paraphrasing, seamlessly transitioned from TV to full time
podcasting and remained hugely relevant. Yeah, yeah, unbelievable. What a
great job.

Speaker 3 (01:23):
Yeah, it was. It was like he took all of
the best moments that he remembered from the Oscars that
he enjoyed mixed in his not just his brand of comedy,
because I felt Smigel, I felt different elements of like.
It was very much a Conan O'Brien Oscars, there's no question,
but where when Dave hosted back in the day, he

(01:45):
would take his sensibility and even some of his bits
and kept them the way that they were. Conan took
things sensibility and again even I would say a couple
of the things that happened would be Conan bits, but
he elevated them and he really morphed them for that
audience so well. And again it was very much a

(02:06):
Conan O'Brien Oscars, but also broad enough that the pop
culture appeal of it was just absolutely flawless. As far
as I'm concerned it was very traditional.

Speaker 2 (02:17):
On Saturday's episode, in my Oscar's preview, I picked up
on an interview where Conan was talking about how he
grew up watching the Oscars and watching the host of
the past, and I noticed at one point, pretty early
in the show, he had that old timey rhythm of
you do a chapter, you do a segment, you switch topics,
for example, Yeah, and how about conclave joke, audience reacts, pause,

(02:40):
and then there's an aura and you do another chuck.
It's almost the same rhythm as a roast where you
goo and Mike Chisholm is here. Hey, he's wearing his
letterman jacket. That's a shock hot. That's not a mean joke,
it's just a joke. And I felt like he had
that old Bob Hope rhythm and Hope gets killed for
the work he did after age eighty. People go back
and watch Bob Hope clips, please. He had the classic

(03:01):
Oscars host rhythm.

Speaker 3 (03:03):
Yeah no, no, no, that rhythm that he had completely the
same rhythm that Conan fans have come to the thing
about it is, it's it's every bit his rhythm as well.
But you're you're exactly right the way that he would
and again you're right again. And also nothing is me.
I'm not trying to just agree with everything that you
just said, but it's all perfectly relevant. The mood of
it was so light. He wasn't mean about things, like

(03:27):
even the opening that he did with the Substance with
to be moore that that is such a perfect Conan moment.
I remember when he owsted the Emmys and he came
through the ceiling of the office and he was in
twenty four and he was in when he came in
when they started the show with a couple of things,
the video montage and then a couple other but the
Conan part where he was mocking or doing a mock

(03:47):
up or a parody of the substance. I was expecting
that he might do that throughout the show for all
of the movies but he all the Best Picture movies,
but he didn't. But he did give homage to a
lot of them, very smartly and very uniquely throughout the show.
I just yeah, again, I'm gushing all over this thing.
But I'm gonna watch it again. I'm gonna go back

(04:08):
and watch Power the Oscars again. It was so good.

Speaker 2 (04:11):
One of the things I jotted down. I did a
substack post this morning, mainly commenting on Hulu screwing the pooch.
So if you didn't catch up on that, Hulu cut
out during the Best Actress Award and never came back.
So yeah, I had a hop on my ship and
head to International Waters to see best pictures, if you
know what I'm saying. But it was like, come on, Hulu,
what are you doing. But as part of the substack

(04:33):
I mentioned I don't have much to say about Conan,
and that is high praise because the gig and you
and I have talked about what the gig is and
the seacrest of it all. The gig is once you
get past the opening montage and you've done your monologue
and you've done whatever the big stunt is at the beginning.
From there on, it's keep the show moving and stay
out of the way. If you and I are having

(04:53):
a conversation right now about Conan O'Brien and he did this,
and he did that, and I did that, other than
just wow, that was really good, really enjoyed it, that's
the wrong conversation to have.

Speaker 3 (05:02):
At the beginning of his monologue, there was a part
where maybe not at the very beginning, he had a
couple jokes out of the way the police sit down
at the beginning that was really funny. But there was
a part where he was walking around and he even said,
I am walking around the stage to show you that
I have control of it. It's almost like he took
a note from somebody who might have directed one of
these things for a long, long period of time and

(05:23):
told him that, and he just goes around and he says, yes,
this is what I'm doing. As soon as he did that,
I'm like, Oh, this is gonna be that perfect blend
of exactly what you're talking about. He's doing what we're
expecting him to do, but now he is taking control
of the ship and gonna take us for a ride
at the same time, and applied the pressure of that
pedal perfectly. He didn't do anything to overshadow it. All

(05:45):
he did was accentuated.

Speaker 2 (05:46):
So let's walk through it chronologically, because I think there
was a point where his comfort level set in and
when he was prancing the stage. I don't think we
were there yet. Yeah, the opening clip the substance parody
very conan. As you suggest, you seem to like it.
I didn't think it landed, don't. I don't hate it.
I'm not gonna kick a can about it, but I
don't think it landed.

Speaker 3 (06:05):
I don't know if it landed or not, but a ditch.
First off, it did for me, but I'm a Conan fan,
and I think that needless to say. It may not
have landed for the pop culture of everybody else, but
it did show. This is a very Conan O'Brien joke,
very consistent with his stuff with the Emmys and whatnot.
But to me, that's where you knew that this was
gonna have his sensibility all over this program.

Speaker 2 (06:26):
I'll compare this performance to pitching a baseball game. I
feel like he may have walked the first batter and
went two and zero on the next guy, and I
was getting a little nervous, and then he settled in
and found his fastball and just crushed it. Because my
next note here is there was an early joke about
a complete unknown and two other things rhythm of three
typical joke, and I could I knew the joke was

(06:47):
coming once he said a complete unknown. Now I thought
the punchline was gonna be. That's what they said about
me back in ninety four, but I still could tell
that it was going to be a joke about him
and a bit telegraphed, and at that point that we're
very early here, I was like, ooh, this could be
rough because the audience hadn't settled in yet. A complete unknown,
a real a real pain. They'll turn out too. These

(07:18):
are just some of the names I was called on
the red carpet.

Speaker 3 (07:22):
Yeah. No, there was that nervous energy and the uncertainty,
and you're right, there was a settling. There was a
settling in point. I'll tell you this. The part where
I got really excited was the John Lithgow gag. It
seems we're not gonna pull anybody off the stage, where
he's gonna show John with a disappointed look in the audience,
pointing it out, doing it perfectly. That also to me

(07:43):
very on brand for Conan, and to me that got
the audience excited as well. The way that he would
interact with people in the audience. I think that's always
a hallmark that does transcend host a host playing with
people in the audience, and many times you might want
to be playing with the biggest movie stars and all
of that sort of stuff. Conan having fun with John
lithgowt to me was a lot of fun.

Speaker 2 (08:02):
Let me sidebar there. One of the notes I had
for the telecast was they did a great job. It
was celebrities that I say that I live on old
Man Mountain. I'm fifty five years old. These were celebrities
that even I've heard of. They but they were current stars.
It wasn't like, oh yeah, they brought out Mark Campbell
from nineteen seventy seven, who they later did you know?

(08:23):
It was today's stars, today's musicians, not quote unquote my people.
It felt very modern. I have the highest compliments for
the production. I'll jump wayhead to the end when they
honored Quincy Jones, So how do we honor Quincy Jones?
And I thought picking a song from The Wiz was brilliant?
High five whoever thought of that? Because it ties the
Wiz to Wicked, which ties the past to today, and

(08:46):
the Whiz is like almost fifty years old now, which
is differently scary. Just a really modern feel honoring the
past being tied to the past. But an oscars for
twenty twenty five.

Speaker 3 (08:58):
My wife and I we talked at length about Wicked
because my wife adores Wicked. This is one of those
movies that we saw it twice in the theater and
then the moment the digital came out, and my wife
was just so excited that they started the show with
Somewhere over the Rainbow. All of the Wizard of Oz
connections throughout this telecast I thought was brilliant, and the Wiz.
I just wish they would have mentioned Michael Jackson's name
to me, that's the uh, you know, the script for

(09:20):
Oprah and for Whoopy talking about all the different artists
that he worked with, But they didn't mention Michael Jackson's name,
but yet they said he was the helm of we
are the world. Didn't mention Michael's name, but then they
showed the Wiz, which, again, you're right, perfect tie in there.
They're a better way to tie him to the relevancy
of this year than that. But I thought it was very,

(09:41):
very safe. It was a very safe copy that was
given to those ladies not to mention Michael Jackson's name,
even though Quincy Jones of course, always will be tied
to that body of work as well. That being said, yeah,
absolutely there was Wicked was all over this thing. Again,
this is what I want to know is how much
input does Conan and his team get to come in
and they get to callborate with this institution that's been

(10:02):
around forever, does Conan get does he get to say
how hard they're going to press the wicked pedal versus
say some of the other pedals that he could press.
I'm super curious about that.

Speaker 2 (10:13):
After I let Mike go, I went upstairs to grab
an iced coffee with caramel mil because you know, and
I realized I didn't answer his question about the production
of it all, and I do want to just address
that because I feel like I have something to say
about it. I've produced a few things in my life,
nothing on the scale of the Oscars, but I've produced
a few things. As for Conan's involvement with the rest
of the show, in my experience as somebody who's produced

(10:34):
things on and off for thirty years, what would happen is, uh,
so you've got a host lined up and then on
the suits end, So I'll put myself on the suit's end.
I would grab my team and start spitballing. Okay, what
could we do with host who's got some ideas? And
we would come up with a million ideas, and then
the leader of the project, me would contact the talents

(10:58):
principal person. So in this case, if I'm producing the Oscars,
I've got my team, We're bouncing some ideas, and now
I'm going to whoever Conan's guy or gal is and saying, hey,
do you think Conan would be into any of this?
That person, having the position of being Conan's guy or gal,
knows how Conan thinks and is like, no, he would
never do that. He might be into that, let me

(11:19):
bounce it off him. And then then that person would
go to the host, get some feedback, and then come
back to my team and tell us the yeah, no,
he doesn't want to do the thing with the pony.
I thought the thing with the basketball was kind of fun,
and there's no way he wants to do the thing
about geopolitics. And then from there you would shape the
show together. But that's my experience. Anyway, back into Mike.

Speaker 3 (11:40):
Does Conan get does he get to say how hard
they're going to press the wicked pedal versus say some
of the other pedals that he could press. I'm super
curious about that. Me and Robert Morton are gonna be
talking about this. I was Mexicano, no great messaging him
throughout the telecats. I said, if you've been talking to
Jeff Ross and he said all day? And I was like,
oh gosh, I want to know more about those conversations

(12:01):
because I really want to know how much input these
guys had into the substance of the show, rather than
just the acides between the substance that was there. I
want to know how much collaboration was there.

Speaker 2 (12:10):
You know, you get better, guess I get you.

Speaker 3 (12:16):
I don't know if I don't know if we're gonna
make it a letter in podcast or now we're doing
a phone call and we're gonna talk about it. But
he may he may be coming on for that. But yeah,
Jeff Rock Spigel all over this thing. Well, yeah, the
chronological thing I think is a good idea. But I
want to go back to that the film that they
did trying to teach people that the communal streaming service
going to the movie theater. I loved that video so much.
I didn't know if that was the Smigel piece. I

(12:37):
felt like it might have been, but again, feels like
a cone and piece, but elevated and pop culturized for
that audience. I love that segment.

Speaker 2 (12:45):
No, everything just fantastic. All right, So going down my
chronological so at some point he prancis the stage. Yeah,
we've covered that. I felt when he started bantering with
Timothy Shalla may is when he got comfortable, and then physically,
I felt like Conan knew he had the room, now
that the room had his back, that this wasn't going
to be Letterman two or whatever other oscars we want

(13:06):
to talk about. He knew he had the room. So
now he's more confident and he's now he's just throwing fastballs.

Speaker 3 (13:12):
Yeah, and again keeping it very very One of the
things that I loved about this is that Conan has
clearly interacted with these stars and these megastars forever, because
he's got this level of comfort with these people, whether
it's perceived and it's just because of how professional he is,
or because he actually has a relationship with some of
these people. Like it was seamless going from the opening

(13:35):
Hullabaloo to then bringing out Robert Downey Junior. Again, they
really started this thing by throwing fastballs somewhere over the rainbow,
but then the main song Unlimited, from which it was
just absolutely like, how do you top that? She came
in and they absolutely belted it out. It was perfect.
Conan does his opening, he lands it, and then he

(13:55):
brings out Robert Downey Junior. I love the best supporting
act way that he did, the best supporting actor. How
he get to monologue about every single one of the performances.
And again, this is arguably you talk about pop culture
in the modern times, one of the coolest guys out
there generationally. And this is where, again I want to
know how much input there was, because it was just

(14:17):
a perfect thing to do. It was like follow this, now,
follow this. They started at a very high level.

Speaker 2 (14:22):
All right, well, come back and we'll talk about my
friend and yours. Adam Sandler.

Speaker 3 (14:26):
Oh, I'm cool. I can't wait to talk to you
about this. Yeah, very much a Conan bit. By the way, again,
just like lift goal, very much a Conan bit with
one of Conan's people. I know you're not a huge
out of Sadler bit, and I saw your reaction to
it last night, so I'm the happy, optimistic Canadian up here.
I was charmed by it, I really was. I thought
it was borderline brave to do what they did with

(14:50):
Sandler in the audience with the hoodie and the microphone
and allowing him to just be Adam Sandler. You didn't
think it landed.

Speaker 2 (14:56):
I know that I'm in the minority here. I understand
the guy has a ton of money. We were supposed
to take a break here, hold on, we'll be right back. Okay,
all right, Mike's got the giggles here. He apparently really
likes Adam Sandler. Look, I'm obviously wrong. Adam Sandler has
more money than anybody. He has all these successful films.
In whatever Hall of Fame we're going to make, he's

(15:16):
going to be in it. I just I think he's
a fantastic dramatic actor.

Speaker 3 (15:21):
Uncut.

Speaker 2 (15:21):
Jebs is a great film, and he did that to
show off that he can act. So please do more
of that. The recent thing, I don't know what was called,
the thing where he was in the spaceship with the alien.
He's really good in that. That was really good. Do
more of that, please, But that bit last night where
he's in the audience and he's dressed like quote unquote
Adam Sandler and Conan's giving him the business, it wasn't funny.

(15:42):
Now the rest of the Internet found it funny. The
rest of the Internet is gonna go see Happy Gilmore
and say it was the funniest thing. I obviously just
don't get it, but you liked it.

Speaker 3 (15:51):
To me, it was very much a Conan bit and
Adam Sandler, like him or don't like him, A lister
like he's in. He's one of these. He's one of
these A listers that in previous Oscars hosts have fun
with some of these people. You know, growing up with
Jack Nicholson many times is in the front road, he's
smiling with the sunglasses or whatever. This is Conan's version
of that. In my opinion, not saying that Adam Sandler

(16:11):
is Jack Nicholson, but he's an A list star and
it's very much on Brent. It's a mashup of the
Oscars in Conan O'Brien's sensibility and friends. As far as
I'm concerned.

Speaker 2 (16:21):
Somebody mentioned I think also on Threads Sandler would be
a good choice to host the Oscars. He's got the chops.
We've seen he can do the sentimental again. The guy's talented.
I just don't find some of the artistic choices he
makes to be funny. But he's got a toolbox. I
just wish he would use different tools. I think he'd
be fantastic hosting the Oscars.

Speaker 3 (16:42):
Oh, Adam Sandler could absolutely knock the ball out of
the park when it comes to that. He's got again
the collaboration that he has at his fingertips with people.
I think would be really special for something like that
to pivot a little bit again, staying in the vein
of Conan and his friends and people he admires and whatnot.
What point did you notice that Nick Offerman was the
announcer for the Oscars. I thought that was I don't

(17:05):
know if it was after the first commercial break or whatever.
I'm like, I think that's I said to Candy, I
think that's Nick Offferman. And then of course he comes
in later for a bit even better. But what a bold,
fantastic choice for the announcer for the Oscars having Nick
Goferman there.

Speaker 2 (17:19):
I think I had the same timeline as you around
the second commercial break, because I was like, wait, I
know that voice. That's Nick Offerman, because I recognized his
particular delivery as the character of the president from the
movie Civil War. He was doing that kind of read
and then I couldn't get that out of my head.
I kept picturing that very serious Nick Offerman president doing
the VOS so yeah, around the same time, I did

(17:40):
Google just to make sure before they did the one
minute bit. I'll play that here for people who missed it.

Speaker 1 (17:45):
This is Conan O'Brien's first time hosting the Oscars.

Speaker 2 (17:52):
That is true in a culture, it is all about.

Speaker 1 (17:56):
A lot of pressure.

Speaker 2 (18:00):
Not really, I've hosted a lot of shows, Emmy Awards,
Music Awards.

Speaker 1 (18:03):
Well nothing this big, Nick, do me a favorite.

Speaker 2 (18:08):
Please stop interrupting.

Speaker 1 (18:09):
Okay, okay, guy, just trying to help, all.

Speaker 2 (18:12):
Right, Fine, the movies we honor tonight, explore the.

Speaker 1 (18:15):
Challenge this big, coming so late in one's career, must
weigh on a man's soul.

Speaker 3 (18:22):
That's enough.

Speaker 2 (18:22):
Just write the script I gave you.

Speaker 1 (18:25):
He's one of the great comedians of our time.

Speaker 2 (18:28):
Conan O'Brien, perfect, Thank you our OSCAR announcer, Nick Offerman,
Thank you, Nick. Fantastic clip.

Speaker 3 (18:40):
Just so much fun.

Speaker 2 (18:41):
Right, it was great that.

Speaker 3 (18:43):
And little nuds throughout the night. Again, I'm a huge
Amy Poehler fan, and the idea that Nick got to
have a little bit of fun with Amy Pohler was there.
Just yeah, again, this is that collaboration I was talking about.
Conan brought our version, that the audience's version of his people.
You think about some of these people that he you
would have say with Conan O'Brien. All over the show.

Speaker 2 (19:02):
People on the internet were losing their mind that the
announcer got Amy Poehler's name wrong, which was doubly funny
to me, Just so good. What things you gotta be
in on the joke?

Speaker 3 (19:11):
Yep? All right.

Speaker 2 (19:12):
So at the end of the monologue he goes into
a musical piece called I won't waste time. I'll throw
the ball to you.

Speaker 3 (19:19):
I think anybody who's been a long time Conan O'Brien
fan knows his experience with The Simpsons and the idea
of the mono rail song, and I think a lot
of people were hoping that Conan would get his monorail
song moment he did. I don't think it was too long.
I think it felt fairly short to me, and I
thought that he did a very good job of it,
and to me, that itch for a mono rail song

(19:41):
type presentation was completely scratched at that moment, and I
was grinning ear to ear.

Speaker 2 (19:45):
I think I suffered from Montareel syndrome that especially because
he had some sort of stick cane something in his hands,
and my brain was just like Montoreil, Montoreel, and I
needed mono rail level and this song was not montail
level or boy, that's a high bar. So I came
away from the song a little disappointed. It might be
one of those things if I rewatched the Oscars seven times,

(20:07):
that it might grow on me over time. But last night,
in the moment, I was like, but it was good.

Speaker 3 (20:13):
Yeah, oh yeah, but to me necessary it's again mashing
up that cone in sensibility with this time honored tradition.
In my viewpoint, the ouscers typically have a presentation like this.
Sometimes it lands, sometimes it doesn't. If you're gonna stay
with the traditional and you're gonna make that happen, this
is a Conan way to do it. And again, I
gotta be very like, I liked the length of it.

(20:34):
It felt short to me, and I think that's very
important because it could have been a one note joke.
There were a lot of things that could have been
one note jokes that surprised me because they flower, they
had a blooming and then a second blooming and it
actually came out that one actually did for me. It
held my attention the whole time.

Speaker 2 (20:50):
Can you bring Conan back and stay with me here?
So if you went back to say, Jimmy Kimmel, now
you're going down the middle straight host, he does a
fine job. Nobody complains that Jimmy Kimmel hostly. Somebody can
about everything, but for the most part, Jimmy Kimo hosted
the Oscars. People aren't like, what that's crazy. If you
go back to the Conan, well, now we kind of
know what it does. Okay, he's gonna come out and
he's gonna do some quirky stuff. I wonder if he'll

(21:11):
do a song. Does the conanness of it wear off
if he hosts it two, three, five times? Do you
need more of a traditional Kimmel style host?

Speaker 3 (21:21):
And I wasn't sure if we were going to jump
around or not, but we have a little bit like
the when he brought out Billy Crystal and Meg Ryan
at the end and he reminded the audience about Billy
Crystal's dominance hosting this show. You talk with these people
who are at the tippy top. Billy Crystal at the
very tippy top of Oscar hosts, and how Billy would

(21:41):
reinvent himself when he would do it, and he would
do it, maybe take a year off and Letterman comes
in and then Billy comes back. I think that's how
it went. I think Billy had done it before and
after Letterman and the idea that Conan could come back
and he's surrounded with Mike Sweetey and Robert Smigel and
all of these collaborators. That's the beauty of having a
late night host do this, somebody who literally did the

(22:05):
same thing every night, and their charge was to make
it original and fresh and funny as much as they
possibly could. If you got a year in between, with
all of the comedy goal that comes from the year
of those movies that were there, I think absolutely there's
no question that Conan could come back and keep it
fresh as early as next year. Could he do six

(22:27):
or seven in a row. It might be like the
Billy Crystal thing where he takes a year or two
often then comes back. But I think he could do
two more years of this, just using the movies of
the day as the backdrop for the new comedy that
comes out with that same framework. That we've been talking about.
I absolutely think he could do it again.

Speaker 2 (22:46):
Do you think we're at a peak Conan moment right now?
And there's been a few over the decades, but I
think today, on this Monday as a peak Conan moment.
Could you see Netflix or more likely in HBO Max
taking the millennium route and going pretty good at TV?
You want to be way of these here's some cash?
Or is the guy in the sixties, he's got a podcast,
He's got enough money. You're just gonna be competing against

(23:09):
your past selves. The same question we had about Dave.
Is there even a reason to do it at this point?

Speaker 3 (23:13):
I remember when he talked about leaving the Late Night
Show as not the franchise itself, but actually the genre
and what he was gonna do, and the deal that
he had signed with HBO or Max whatever it was.
The idea of the travel show made so much sense
Conan without borders. Yeah, let's keep doing those. If we
get a few of those a year, we're satisfied. But
then the other thing was the idea of the sketch show.
And I mean, that's been very quiet about that. That

(23:36):
to me would be I was so curious about what
that was gonna look like. Would it be you know,
Lauren Michael's new show, or would it be something that
is entirely Conan to me and Canadian think the kids
in the hall, Like, the kids in the hall are perfect,
and they're so quirky, and there aren't that many of
them compared to say something like Saturday Night Live. I
wanted to see Conan do that. And if you're gonna
talk about backing up a brinkstruck and giving him free

(23:59):
rein to do something, I love that idea. But once
a year to do the Oscars too. Oh my, you
could tell that the Again, I talk about the idea
that my wife cooks with love and that's our intangible ingredient.
This show was made with a lot of comedy love.

Speaker 2 (24:14):
Oh yeah. So I think part of the matrix here
is and I'm projecting like in my own career and
I'm obviously not at all famous. I'm just some dude,
but I've had points in my career between gigs where
i would feel like, oh, I used to be John McDermott.
People used to take John McDermott's calls. But being entertainment
adjacent when you have a big fancy title. People take

(24:35):
your calls and when you were a dude in the
basement podcasting, some people take your calls because they were
true friends. And some people have no use for you anymore,
so they don't take your calls. So, for Conan, is
the podcast enough or is it at?

Speaker 3 (24:48):
Oh?

Speaker 2 (24:48):
At some point I used to be Conan O'Brien. At
some point I used to be David Letterman. Now Johnny
Carson was fine being its. I used to be Johnny
Carson and went away. Dave seems good. Does Conan need it?
Or is once a year enough? Is the podcast enough
or never again enough? Or would a Netflix thing be intrigued?

Speaker 1 (25:05):
Oh?

Speaker 3 (25:05):
Look at the name of his documentary, outlining the period
between when he lost the Tonight Show and when he
started the TVs show. What's the title of it? ConA.
Brian can't stop. And I truly believe that he can't stop.
I think he's at the place now where he's lucky
enough to say, this is what I'm going to do,
These are the things that I'm going to be a
part of in my infinite energy for these things. To me,

(25:26):
that was a guy who was energized, did not need
to my as a fanboy, like, oh, wouldn't it be
cool if Kimmel or Letterman or some of these other
people who hosted in the past were there were not
you know, he could reference some of these things and
make that's the fanboy and me coming out. But then
I see the presentation of him going up there and going, oh, no, no, no, no, no,
he is I said it. I think I might have

(25:47):
said it on this show too. When he went back
to The Tonight Show earlier this year or in twenty
twenty four, he came back as a guest of The
Tonight Show, and my first response was he seems way
bigger than the show. Conan seems way bigger, and his
podcasting dominance, I think is one of those things where
people will continually pick up the phone because, yeah, you
do want to be on Conan's podcast, like you wanted

(26:09):
to be on the late night shows before the dilution
of the audience the way that they did. I think
people want to be on his podcast for that reason,
and that keeps him relevant right there. But I do
believe the Conan O'Brien name is big enough that he
will always be relevant. Now he is, He's a giant
he really is. Last night was for many people. I
think just like the Emmy's back in the day. I

(26:31):
think that the Emmy's back in the day when he
hosted that surprised a lot of people. I felt like
that same level of surprise might be happening to a
lot of people out there, going, Oh, Conan's still around.
For those of us who still love this stuff and
listen to his podcast, we're like he never left and
he's only getting better with age.

Speaker 2 (26:49):
It's interesting that you go from being underground and an
acquired taste to a day like today as mainstream as
it gets.

Speaker 3 (26:57):
Absolutely absolutely something else. I want to note there was
a moment when Kimmel hosted I think it was last year,
where he made a real time Donald Trump joke. It
was during the performance, and it was something that had
happened during and he made a reaction a joke, a
reaction joke during the actual Oscars, and I forget the
joke whatever. I was wondering if Conan was going to

(27:18):
have any real time type moments where there would be
stuff that would carry through the show, and the idea
of when the Latvian crew for Flow won their first
Oscar they talked about that and Cona's response, your Move Estonia,
and then he called back that your Move Estonia a
couple of times throughout the show, which I thought kept
it fresh. To go back to that point, the idea

(27:39):
that it wasn't just a canned performance, that it was
a live thing where he could also show his improvisation
chops as the show moved flowed through. I thought that
was a really neat addition to the program as well.

Speaker 2 (27:51):
It's hard to make those editorial choices. You want to
live in the real world. You have to deal with
things that are obvious, for example, the La wildfire. Yes,
if you start getting into American politics these days, you're
going to lose half the audience whichever direction you steer
that conversation. If you get into the Middle East, you're
going to lose half the people, depending on which way

(28:12):
you steer that conversation. We can get into the ridiculous
relationship America and Canada have right now. I'm glad you
and I are still getting along. These are just places,
much like the Michael Jackson reference, let's just not go
there and do something else. And I've gotten into this
in my career. That's not censorship. That's choosing differently. I'm
going to choose to not ask you about the fifty

(28:34):
first state today. It's not why you're here. We're here
to talk about Conan O'Brien. Maybe some other time I'll
ask you about that topic, but it's not why you're here.
So I don't need to go there. You possibly have
some views on geopolitics, it's not why you're here, so
I don't need my audience going. You know, I really
like that Mike from the Letterman podcast. He was really cool,

(28:54):
but I totally disagree with his take on X and
now everyone or half the people dislike you because it's
not what the show is. So I think it was
a smart decision, yep, not to do it now. As
for the speeches, if you get up there and you
get your time I like when people get up there
and use their time to you know, you get a platform,
use it. I think that's a good thing. And I

(29:15):
don't think that's contradictory to what I just said. One
of the questions I have from the production standpoint is
rushing people off the stage. What are we rushing to?
Are we we just rushing to the American Idol Special
or the eleven fifteen PM News. Let people have their moments,
like at some point, okay, you gotta stop, but like
forty five second clocks, especially when multiple people have won

(29:37):
an award. Let people have their moment. It's why we're here.

Speaker 3 (29:41):
I the more I see him do things, the more
I enjoy Adrian Brody and some of his antics. He
does have antics, the infamous snl antic when he introduced
the musical guest addressed in Rastafarian with a Jamaican accent,
and things like that. During his acceptance speech, the idea
where I've done this before, I'm gonna keep talking here,
do not play me off, and then after the thingk

(30:03):
he did actually give what I thought to be Sometimes
these socially conscious messages are out of touch. I thought
his was actually really good. It was universal. I don't
think it was walking Phoenix talking about private jets. I
didn't think it was like that. I thought he did
a good job with it. Some of the people who
would come up and be out of sorts, like it

(30:25):
was the winners for Flow. I think that had the
phone and they read the speech and it was Yeah.
I like allowing moments like that to unfold and to
breathe because they can then become something else, and if
they run the ship so tight that it can't. I
don't even know how over the telecast went. I know
we always record the next show on the DVR as well,

(30:45):
and I think we watched maybe ten minutes into the
American Idol show. I think that was if there was
an overrun there. I think it was only about ten
to fifteen minutes. I don't think it was that long,
but they were making fun of themselves all night for
it being so long, so I didn't care. I didn't mind.
They acknowledged it. And when you allow moments like that
to happen, to me, that's a better trade off and
it feels like you're getting something special rather than something canned.

Speaker 2 (31:07):
As part of the leadup, Conan actually said he was
hoping something would go sideways because that's where the magic is.

Speaker 3 (31:12):
He's so right every time. Why do we love Letterman
so much? Because whenever something went sideways, Now it's a
new show. Now it's something else where, uncharted territory, and
nobody knows where it's going to go, including the producers
of the show themselves, And to me, that's one of
the magical feelings that that Letterman brought to us and Conan.
That was one of the ingredients the bones that Conan

(31:33):
continued with the Late Night with Conan O'Brien franchise that
they took from Late Night with David Letterman, And sometimes
they would plan these moments again to go back to
a Conan bit, a very Conan bit, the dune sandworm
funny the first time, as a Conan bit funny the
second time. Because it's like that thing was so expensive,
we had to use it twice and I just, oh,

(31:53):
what a perfect Conan bit. And it wasn't unpredictable necessarily,
but at the same time, it was a little bit.
It was the him out of Pewe's Playhouse, I guess
I would say, yeah.

Speaker 2 (32:02):
And it just shows you the when things go sideways,
the value of a quarterback, whether it's Conan or Dave
in his element or a Kimmel. I was speaking with
my wife over the weekend about the Will Smith incident
and a few years later here in everyone's mind, I
think everybody thinks Chris Rock hosted the Oscars that year.
He didn't. He just happened to be there when things

(32:23):
went sideways. And recovered pretty nicely. And I don't think
the trio of hosts that year really stood out when
things went sideways. There's another situation where the slap happens
and now we throw the ball back to Conan. That
gets handled a lot differently.

Speaker 3 (32:39):
I think I could not agree more. That's somebody that
you want to be the host of that show. I
remember Chris Rock hosting the MTV Video Awards when I
was growing up. I consider Chris Rocker host that the
year of the slab was that was that Amy Schumer?
That that was Amy Humor that hosted it.

Speaker 2 (32:54):
Which which again my audience. So we've been talking about
Amy a lot lately. If I walked up to you
and I said, Hey, who's hosting the twenty twenty sis
Oscars is Amy Schumer? Wouldn't you think?

Speaker 3 (33:02):
What?

Speaker 1 (33:03):
What?

Speaker 3 (33:04):
Yep? Yeah, one hundred percent? And you're right, that's a
good example of a show being on rails, never mind
how the host has reaction reacted. All that show was
so on rails that Will Smith Gott could could slap
Chris Rock and then be celebrated like an hour later
when he went up at That show was very on
rails compared to last Night's did not seem that way.
It did seem fresh and unpredictable. And yes we're acknowledging

(33:26):
that it's long. Conan made a Stockholm joke, a Stockholm
syndrome joke about that. It felt unpredictable, and I think
that the late night hosts many times bringing I think
Kimmel brought that feeling when he hosted as well. I
think Billy Crystal when he hosted the show back in
the day and did it such a masterful job of it,
brought a little bit of that. But the late night
hosts bring a special version of that because that's their brand,

(33:47):
that's what they do.

Speaker 2 (33:48):
So last thought for me, I'm gonna hop in the
time machine. I'm going to go back to the Wednesday
of Conan's first week as the host of Late Night,
and I'm going to tell everybody in thirty years, this
guy's going to the Oscars and crush it.

Speaker 3 (34:01):
I think would not be surprised by that. Some of
the people who I was just talking to George Meyer
this week, and George is a legend comedy legendary comedy writer.
We were talking about the Lauren Michael's book. He talked
about the moment that Conan was vying for Late Night,
and originally the idea was that he would be might
be a head writer, one of the head honchos for it,

(34:24):
and nobody considered him host. George was one of the
guys that said to him, hold out for the host job.
This is when Conan O'Brian was a writer for The Simpsons.
They've got the Harvard Alum National Lampoon background together just
from different eras a little bit. George saw it because
he would see Conan putting on these shows for the
other Simpsons writers and how special of a talent he was.

(34:47):
The idea of replacing David Letterman. Yeah, I'm gonna be
on part of Late Night, this new this franchise that
David Letterman built, and we're going to be continued at NBC.
Somebody actually says to this, not to put any pun
into this show, but a complete unknown and saying no
hold out for the host job. That's a ridiculous thing
to say to someone like that. But George and people

(35:09):
who were around Conan on a small scale back then,
I think could say thirty years from now, this guy
could be hosting the Oscars. I think that there were
elements of him. Again, I think the Conan who was
at Late Night that signed the five year deal. The
reason the five year deal existed was because of the
Conan we saw last night. That was the Conan that
did host the Emmys. Back then, that holding deal that

(35:29):
NBC signed with him was because they did not want
to lose this giant talent. And how many years later
are we go ash he signed that deal and what
five twenty years ago? He was that big and people
saw it that much twenty years later. Conan's a smart investment.

Speaker 2 (35:44):
Such a bolds pick back in the day. Why not
just hands twelve thirty to Gary Shandling or somebody like that.
And just kudos to everybody involved in making that decision
for being able to recognize the talent he is.

Speaker 3 (35:56):
And again he's that. I listened to his podcast all
the time. It's so natural to me to listen to
that show. I enjoyed watching Conan. My golden age for
late night television was when Late Show was on, then
Late Show with Craig Ferguson and Conan either at the
Tonight Show or his TBS show. He transitioned over to
podcasting so seamlessly and can do these things. The Travel

(36:17):
Show again a very different kind of a show, so
seamlessly and again hosting the Oscars things. I am not
surprised that it went that well. I'm just so happy
that it went that well. It was a delight to watch.
Sometimes these things are a pain in the ass to watch.
Not last night. This was a delight to watch.

Speaker 2 (36:34):
All Right, if I'm going to work an extra hour,
let me take one more break so I can make
twenty more backs. Get back with Mike Chisholm from The
Letterman Podcast. All right, Mike, thank you for taking the
extra time here with me today. What's coming up on
the Letterman Podcast. We've got a couple of it's up
in the air a little bit. I'll tell you something
that's coming along that. So there's a I look at
him as a legendary Letterman writer. His name Steve Weiner.

Speaker 3 (36:55):
Steve wrote for the first year of Late Night with
David Letterman, and he is responding for some of the
bones of that show. The idea of Dave throwing something
behind him, whether it's a card or a pencil, going
through the window and having the glass break. That was
Steve's joke. The other thing that Steve, I would say,
and Steve added a couple of things that went the
entire run, but one of them was a guy by

(37:15):
the name of Calvert DeForest. Larry bud Melman, Steve and
his writing partner actually are the ones that discovered him,
and they had him in their NYU film called King
of the Z's. There's a version of King of the
Z's that's actually really clean. Steve's gonna come on the show.
We're gonna talk about the Oscars. Our good friend Rick
Scheckman passed away two years ago this week, so we're

(37:36):
gonna talk about him as well. But then also we're
going to talk about King of the Z's and we're
gonna do a separate episode where we actually go through
Calvert to Forest's one of his inaugural performances. Together. We're
gonna do I don't know if it's gonna be a
commentary or mystery science theater, how we're gonna do it,
but that's gonna be coming out here soon. So that's
pretty exciting. I think Mordy is coming back on the
show again soon. We're gonna start celebrating the ten year

(37:58):
anniversary of Dave leaving show with David Letterman. So lots
of good stuff coming up on the Letterman Podcast, and
we're gonna have you back too, because you're one of
my favorite guests.

Speaker 2 (38:07):
I appreciate that you're one of my favorite guests and
one of the two people that can book if you
have you and Larry the Cable Guy, if you have
access to Smigel. I'm trying to get to Smiggle for real.
I want to find out about Night of Too Many Stars.
I want to learn more about what the cause is.
And I explain this on my show that I don't
mean it and a like, so where does the money go?
I mean, like, where's the money go? Like, you guys

(38:27):
are doing a cool thing here, tell me more about it.
So if you could put a bug in somebody's ear,
I would appreciate that. I like doing these crossovers with you.
I know from seeing on Facebook we've both picked up
people who didn't know about the opposite show. So I
think this is a good thing. You're always a great guest.
And as soon as I put it together, we were
texting about something else that I was like, Oh, I
should probably just ask you. Now I'm gonna wind up

(38:49):
wanting to talk to you about Codin, so we actually
booked it in advance for one So thank you for
coming on today anytime.

Speaker 3 (38:53):
I couldn't agree more. I love the crossover shows as well.
I do have people who are like, we're one degree
away from Robert for sure. I'll definitely see if we
can get something going there. And yeah, thanks for everything
that you do. Thanks for this show. Actually, I was
just talking to the Late Nighter dot com founder about
you and your show, and I just I cannot endorse
it enough. The idea of catching up with all of

(39:14):
the major events within comedy and doing it in a
very concise way. It's so easy to digest your show,
unlike mine. So thank you very much for everything that
you guys do.

Speaker 2 (39:23):
Thanks for coming on. That is a bonus episode. Tomorrow
another normal episode, a lot of stuff that got bumped
from Monday. South By Southwest chose to announce their comedy
lineup in the middle of a weekend of Shane Gillis
hosting SNL and Conan hosting the Oscars. A lot to
talk about tomorrow, See you then,

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Conan O'Brien Stuns as Oscars Host - with guest Mike Chisholm from The Letterman Podcast

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.css-14f5ked{margin:0;word-break:break-word;display:-webkit-box;-webkit-box-orient:vertical;box-orient:vertical;-webkit-line-clamp:2;overflow:hidden;}Conan O'Brien Stuns as Oscars Host - with guest Mike Chisholm from The Letterman Podcast