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September 5, 2026 • 50 mins

In this episode, Wayne Federman joins the guys to explore the rise of legendary comedian Dick Gregory, who began life as a boundary-breaking stand-up comic. Tune in as the gang explore's Gregory's evolution, his association with Hugh Hefner, and his later calling as a full-time civil rights activist.

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Speaker 1 (00:00):
Fellow Ridiculous Historians, this week's classic episode is something that
really stood out to us. We had an interview years
ago with the legendary Wayne Fetterman. Noel, you remember this one?

Speaker 2 (00:16):
Of course, man. Love that guy. Hold on a second.
I almost want to say that he was involved in
a sketch or a scene in Curb Your Enthusiasm involving tipping.
Larry David loved to joke about the politics of tipping,
but maybe I'm wrong. But he was definitely on an
episode of Curb. He taught classes about the history of

(00:37):
comedy in Los Angeles, and he was kind enough to
talk to us about the progressive politics and scandalous stand-up
of Dick Gregory.

Speaker 1 (00:47):
So let's roll the tape. Welcome to the show, Ridiculous Historians.

(01:22):
Thank you so much for tuning in. Now, you know, also, additionally,
maybe it's just me. I want to thank everyone who
has bothered to chuckle, laugh, snort, laugh through their nose
or occasionally laugh. guffaw at our jokes because comedy is tough.

Speaker 2 (01:38):
Hi, I'm Ben. Hey, I'm Noel, and I've never fancied
myself a comedian. I always say I'm a purveyor of
dad jokes, and I am absolutely fine with that. But
straight seahorse teeth seems to be taking off online like wildfire, Ben.

Speaker 1 (01:51):
It's true, Noel.

Speaker 2 (01:51):
Did you already say your name?

Speaker 3 (01:52):
Yes.

Speaker 2 (01:53):
Sorry. I said, hey, second time's a charm.

Speaker 1 (01:56):
Comedy's all about listening, you know what I mean?

Speaker 4 (01:58):
Oh, Ben.

Speaker 3 (01:59):
Wow.

Speaker 1 (02:00):
It's true.

Speaker 2 (02:00):
Shaming me.

Speaker 1 (02:01):
You know what is pretty cool, though? It's the official
return of can we get a drum roll, please? He
has to do his own drum. Let's go. Super producer
Casey Labouche-Pagram.

Speaker 2 (02:17):
I know. Casey, when you were away, did you hear
that we kind of developed a mythology for you based
on our knowledge of your French goings-ons?

Speaker 5 (02:28):
I caught wind of this, yeah. My sources back here
in the States were keeping me informed of all relevant information.

Speaker 2 (02:36):
You're very tied in, very connected.

Speaker 5 (02:38):
Spycraft, you know, you got to have your feelers out there, so.

Speaker 1 (02:42):
I have a question, and please do not feel obligated
to answer this, Casey. First off, I say this with
great affection. There was a Casey-shaped hole in my heart
when you were gone. Now that you are aware, along
with all of our fellow listeners, about how your alleged

(03:03):
double life in France was portrayed, would you say that
this is accurate, inaccurate? A seed of truth?

Speaker 2 (03:13):
I don't know.

Speaker 5 (03:14):
I don't really want to blow up my own spot
like that. But, you know, I'd say if it's maybe
not true to the letter, it's certainly true to the spirit.

Speaker 1 (03:22):
All right. Okay. I can accept that. Well played. You've
passed the test, my friend. We have, in honor of
your return, we have not a surprise for you, but
a gift for you and hopefully for all of our
fellow listeners today. A while back, I think it was
episode 108 or 109. We did a two-part show on

(03:46):
the history of stand-up with our pal Wayne Fetterman, who
has an encyclopedic knowledge of the history of comedy. And Casey,
we waited until you returned with your U.S. identity to
the studio to have Wayne Fetterman on the show today

(04:07):
for you, dude.

Speaker 5 (04:08):
I know, and I'm so psyched about this because, yeah,
it was like a year ago that I was out
and he was on, and it was driving me up
the wall because, yeah, I'm a big fan of the
guy and a big fan of the history of comedy
and everything else. So, yeah, it's great to be here
for this.

Speaker 2 (04:22):
Well, Wayne is an encyclopedic font of comedy knowledge. His podcast,
The History of Stand-Up, on the Podglomerate Network with his co-host,
Andrew Stephen. It's just a delight. And last time we
had him on, we talked about Lenny Bruce and kind
of some more inflammatory comics that sort of pushed the
envelope of free speech.

Speaker 1 (04:43):
George Carlin.

Speaker 2 (04:43):
George Carlin, however many filthy words, unarable words there are.
I think those are the only two explicit episodes of
the show we've ever had because we needed to be
able to unbleep those words because they were very important.

Speaker 1 (04:56):
To the story. It was about censorship. Luckily, however we
did with that episode, Wayne was a charitable enough guy
that he came back to hang out with us today.

Speaker 2 (05:06):
Not to mention that my mic was cut for like
half of one of the episodes and we still salvaged
it with our crack forensic audio team and made it
at least somewhat listenable. And also Wayne didn't think we
were a bunch of hacks and agreed to come back on,
which I really appreciate. And this episode is fantastic. Another
exploration of some envelope pushing comedy, but in a slightly

(05:27):
different way.

Speaker 1 (05:28):
So without having deep dive demographics on how many of
us are stand-up history buffs, we'd like to introduce you
to a man named Dick Gregory, a pioneer, not just
in the world of stand-up comedy, though he very much was,
but also in the world of civil rights and activism.

(05:51):
So we hope that you enjoy our conversation here with
Wayne about not just comedy and but about progressive actions
in the United States, about civil rights in the 60s,
about the oddly heartwarming actions of the often controversial Hugh Hefner.

Speaker 2 (06:10):
Let's get right to it.

Speaker 1 (06:15):
The rumors are true, ridiculous historians. We are joined once
again with a friend of the show and host of
the History of Stand-Up podcast, Wayne Fetterman.

Speaker 2 (06:27):
Friend of the American people, Wayne Fetterman.

Speaker 1 (06:31):
Friend to our producer, Casey Peck from Wayne Fetterman.

Speaker 4 (06:34):
How you doing, Wayne?

Speaker 6 (06:35):
I really would rather be speaking to Casey. That guy's incredible.

Speaker 2 (06:39):
He may chime in, but you won't be able to
hear him because he's not piped into the phone. But
we will relay any words of wisdom that he provides
on his behalf.

Speaker 7 (06:46):
All right. Is he beaming right now because I'm talking
about him?

Speaker 8 (06:49):
I am.

Speaker 3 (06:50):
He is.

Speaker 2 (06:51):
He says that he is. His face is obscured by
a giant computer monitor, so I can't speak to that person.
But his voice in my ears says that he is.

Speaker 1 (06:58):
Okay.

Speaker 2 (06:58):
And he just leaned in and gave a big smile.

Speaker 1 (06:59):
Fun story before we get started. And this is a
true story, Wayne. When we were putting together this episode,
Casey actually asked us to hold and he traveled all
the way back from Paris, France to be here today.

Speaker 2 (07:13):
Very special trip.

Speaker 1 (07:14):
It's true.

Speaker 2 (07:15):
It's all true.

Speaker 3 (07:15):
Yeah.

Speaker 7 (07:15):
Let me just say that it's very much on brand
for Casey.

Speaker 1 (07:20):
So when we previously spoke together, we looked at the
history of what we call stand up today, not just
as the craft or the actual performance that we think
of with somebody standing with a microphone and an audience
that hopefully loves them, but not always. We also talked

(07:41):
about some of the bigger social questions that stand-up brings
to the forefront and sometimes Those can be uncomfortable questions
that people don't typically explore. Now they laugh at it too,
but sometimes they leave thinking. In our earlier conversations leading
up to today's episode, you started telling us about someone

(08:05):
that was, I think maybe vaguely familiar to us, but
someone we weren't super well acquainted with, which is the
comedian and activist Dick Gregory. Wayne, could you tell us
a little bit about just for our audience, who Dick
Gregory is?

Speaker 6 (08:22):
Well, Dick Gregory is famous in the history of stand-up
for one specific thing, and that is he became the
first major, and there's a caveat, we can go into it, comedian,
African-American comedian, to play white nightclubs. And how that happened,
we will tell you in a moment, I'm sure. But

(08:43):
he was just a You know, he was a funny kid.
He was an athlete. He went to college. He was
in the service. And then he moved from St. Louis
to Chicago to pursue his dream of becoming a stand-up
comedian and could only play the black clubs in and
around Chicago and was really struggling. Actually had a day job.

(09:04):
He worked at the post office. He washed cars, all
trying to subsidize this career of his.

Speaker 7 (09:11):
And at this point, he's married. He has a lot
of responsibilities.

Speaker 2 (09:14):
So leading up to this big moment that we're going
to get into that involves another kind of historical luminary
and controversial figure, Dick Gregory was kind of doing his
best to get into the kind of Chicago stand-up nightclub scene.
And as you said, it wasn't a very welcoming scene
for people of color. And I want to play this
clip from American Masters on PBS where Gregory kind of

(09:37):
describes this moment. where he had to disarm a white
audience at a club, I want to say in Alabama
or something like that, where someone calls him a racial slur.
And he has to take that opportunity to diffuse the
situation rather than make a scene and, you know, put
his career in jeopardy because these were ultimately his clients

(09:57):
So he was there to entertain. So I think this
really is a very teachable moment about the kind of
climate that he was dealing with.

Speaker 4 (10:03):
So I go down there and I'm not thinking of anything.

Speaker 8 (10:07):
I didn't know at the time that a Negro is
not permitted to work a white nightclub.

Speaker 4 (10:12):
That's in all of America. And I remember not knowing that.

Speaker 8 (10:17):
I used to practice, what do you do when some
white person yells something negative out or embarrass you? And
so I used to practice with my wife, but it
didn't work because she was too nice and kind. And
then one night, I don't know how I got this
little job in this little hick town, little Mishawaka, Indiana.

Speaker 4 (10:38):
You don't have to say no more.

Speaker 8 (10:40):
So I'm in Mishawaka, Indiana, and somebody said, Get that
nigga off the stage.

Speaker 2 (10:49):
Now, I was ready for it.

Speaker 4 (10:52):
And everybody just froze. And I said, yeah, white boy,
call me, call me. All Rangers hearts, call me Trigger.
And everybody laughed. I'm out of it. There's no way
you can feel sorry for me or embarrassed and laugh.

(11:13):
So now I got them back. Now I'm off. You know,
and the guy walks up and says, whew, thank you.
Jesus Christ. I wanted to hit him myself. And then
the guy walks up and says he's sorry.

Speaker 3 (11:26):
Sorry?

Speaker 4 (11:27):
I almost paid you, man. I've been trying to figure
out how to get through this.

Speaker 2 (11:30):
So, Wayne, I wanted to know if you thought that
maybe this was kind of– he would have had to
deal with similar situations like this leading up to this moment.
And he almost describes it as like an aha moment
where it's like, aha, this is how I can deal
with this kind of heckling. Right.

Speaker 6 (11:46):
Well, I feel like Dick Gregory, especially at that time,
had a very high emotional and comedic IQ on how
to handle crowds. And it's remarkable considering he's not that
experienced other than basically playing these black clubs. But I
just think he had an innate sense of, one, how

(12:07):
to perform in front of white audiences, and two, how
to diffuse these very volatile situations that I'm sure would
come up all the time.

Speaker 3 (12:16):
Right.

Speaker 1 (12:16):
Because as, as you had mentioned before, he was, he
was working, let's see, his comedic career began in what
the mid to late 1950s. Is that correct?

Speaker 3 (12:27):
Yes.

Speaker 1 (12:27):
Yes.

Speaker 3 (12:27):
Yes.

Speaker 7 (12:28):
That's exactly correct.

Speaker 6 (12:29):
And at that time there wasn't a lot of, uh,
you know, African-American comedians on television or on the Ed
Sullivan show.

Speaker 7 (12:36):
It was just a few.

Speaker 6 (12:38):
And once in a while he'd see somebody and there
really wasn't a, A big circuit to play. There was
big white nightclubs, which we called nightclubs at that time.
But they wouldn't use African-American comedians. Once in a while,
they would. But as a rule, they'd have an act.
Sammy Davis could play there or something like that. Or

(13:00):
a team or a singer like Pearl Bailey or something
like that all the time.

Speaker 7 (13:06):
But not a stand-up.

Speaker 2 (13:08):
I saw a really interesting clip with the comedian Paul Mooney,
who was another very outspoken comic, a contemporary, maybe a
little younger than Gregory, but still kind of very much
like in the same scene as Richard Pryor. So maybe
like the next generation. But he talked about how in Hollywood,
nothing could ever be too white, but it was very
easy for something to be too black. Um, and I

(13:29):
think that's a really interesting distinction where like you talk
about Sammy Davis juniors and like performers of that caliber,
they were a little more palatable to a white audience,
but a comic like Gregory who wasn't pulling any punches,
that would be a little harder to take for these
folks who maybe weren't used to seeing things like that.
Is that, would you say that's accurate?

Speaker 3 (13:45):
Yes.

Speaker 6 (13:46):
Mooney is a hundred percent on, on like people would go, okay,
this is, this is too much for us. But again,
Dick Gregory, I think really learned how to thread the
needle almost like in a, um, Jackie Robinson kind of
way that he was like able to like take white
audiences expectations of what a black guy would talk about.

(14:07):
And he talked about racial stuff all the time. That
was the centerpiece of his act, but he did it
in a very non-threatening, very human way, as opposed to
an angry way in that same NPR or PBS clip
that we just heard later on. He talks about that
he was always respectful and that he wasn't bitter and

(14:27):
that he wasn't angry. And this was all, I'm sure, underneath.
But again, I just feel like his emotional IQ was
through the roof on how to handle these situations. So
he wasn't like Paul Mooney, who would not, you know,
I can't imagine Paul Mooney handling that situation in that
club the same way.

Speaker 7 (14:48):
It would be way more confrontational.

Speaker 1 (14:50):
Yeah, absolutely. I agree 100% with that statement about emotional IQ. Recently,
this is not a plug. I actually do listen to
the history of stand-up.

Speaker 3 (15:01):
Oh.

Speaker 1 (15:02):
Yeah, as season two started. And in season two, you
guys just had an episode come out recently about the
Playboy circuit. And this was something that I didn't recognize.
This episode, for anybody listening, is available now when our
episode comes out. So give it a listen. This brings
us to something that we'd love for you to explore

(15:24):
with us here, which is the interactions between Dick Gregory
and Hugh Hefner, the mastermind behind Playboy Magazine, later the
Playboy Empire. Noel, this is something you were alluding to
in the beginning, right?

Speaker 2 (15:38):
Yeah, for sure. And this Playboy Club, I didn't realize,
was a big source of, you know, entertainment.

Speaker 3 (15:45):
Huge.

Speaker 2 (15:45):
And, like, massive, you know, opportunity for working comics.

Speaker 1 (15:49):
Yeah.

Speaker 2 (15:50):
If you got a regular gig at the Playboy Club,
which was in Chicago at the time, that was a
massive break for you. Can you tell us a little
bit about how Dick Gregory literally kind of stumbled his
way into this massive break? The story is fantastic.

Speaker 6 (16:04):
Well, this is I assume this is why I'm talking
to you guys. This moment is very important in the
big history of stand up. And we covered it briefly
in our first season and then went a little closer.
And thank you for the kind words about the Playboy. Episode.
I appreciate it. For anyone, it's the eight of us
that are interested in the history of stand-up.

Speaker 7 (16:25):
So this is what happened.

Speaker 6 (16:27):
February 29th, 1960, the first Playboy Club opens.

Speaker 7 (16:31):
You're like, what does that mean, a Playboy Club?

Speaker 6 (16:33):
Well, in 53, real quickly, Hefner publishes this magazine, December 53,
called Playboy. Marilyn Monroe's on the cover. There's no date
stamped on it because it might have been the last one.
And it basically has nudie pictures in it, but nothing
too graphic.

Speaker 7 (16:51):
I hope that's clear what that means.

Speaker 1 (16:54):
Yes. Yeah.

Speaker 6 (16:55):
And then like articles and he was into literature. And
so anyway, this magazine out of Chicago, this kid who
had this dream becomes this runaway success in the 50s.
So he is like printing money by.

Speaker 3 (17:09):
57, 50.

Speaker 6 (17:09):
It's outselling Time Magazine. It's outselling Esquire. It's like this incredible,
and has a big female readership as well. So he,
three things happen around this time. One, he does this
huge indoor jazz festival called the Playboy Jazz Festival. Two,
he buys a mansion in Chicago and they call it

(17:32):
the Playboy Mansion, which is like this party house. And three,
he opens the Playboy Club. And also four, there's another
thing I'm forgetting. He starts this syndicated television show called
Playboy's Penthouse, which is this black and white in the
first two years. And you kind of get, it sort
of presents like this party that you're invited to. So

(17:54):
people are sitting around and they're drinking and they're smoking.
And there's a guy playing piano and suddenly Sammy Davis
comes in and sings. And then Lenny Bruce does some comedy.
It's just a very incredible like insight into like the
world he wants to create.

Speaker 2 (18:09):
Hefner.

Speaker 1 (18:10):
And that was kind of like a variety show for him, right?
Is that where we get that idea of him with
the pipe and the smoking jacket and the whole nine?

Speaker 3 (18:16):
Yes.

Speaker 7 (18:16):
Yeah, yeah, yeah.

Speaker 6 (18:17):
But it's not, it is a variety show, but not
on a proscenium stage in like a living room. And
then we, let's go over to the dining room and
then let's get some cocktails made over here. And let's
listen to Cy Coleman play witchcraft. And then it's, it's
just a great like promotional tool for the Playboy brand,
which was, and we talk about it in the podcast
that he was going for sophistication like that was his

(18:42):
like he thought, God, if I could make nudie picture,
you know, this part of a sophisticated lifestyle with high
fidelity and sports cars and jazz music and great literature
that and that's what worked.

Speaker 7 (18:56):
You know what I mean?

Speaker 6 (18:57):
So it was like suddenly not a smutty behind the
counter kind of embarrassing thing if you wanted to see
pictures of beautiful women. So that was another genius, Hugh Hefner.
So he's killing it, killing it during Eisenhower's administration. So
he opens this Playboy Club, February 29th, 1960. And the

(19:18):
Playboy Club was this, you had to pay $ 25 and
you got a key, literally a metal key. It later
became a card. And that gave you access to the
Playboy Club. You were like a key member. And to
serve these men, it was a men's only club, but
you could bring women. They created the Playboy Bunny, which

(19:38):
is different than the Playboy Playmate, which were in the magazine.
And the bunny, how would you describe it? I'm going
to throw it to you because I feel like I'm
talking too much.

Speaker 4 (19:47):
Yeah.

Speaker 2 (19:50):
Were kind of hostesses. They would receive... the gentlemen and
their dates when they'd come in, speak to them by name,
make them feel very welcome and kind of cater to
their needs.

Speaker 1 (19:59):
It was similar to the idea, I guess, we would,
an analog would be a hostess club in Japan. You know,
these people are not necessarily what we would call sex workers.
They hang out with you. They laugh at your jokes.
They converse with you. There were also, there was also
a uniform that changed over time.

Speaker 3 (20:17):
Of course, yeah.

Speaker 1 (20:18):
But that was like, from what I remember- Thanks again, Dad.
I'll admit if you're listening to the show that I
did steal some of your Playboys.

Speaker 3 (20:26):
Vintage.

Speaker 1 (20:26):
From what I remember with the advertisements they used to
have in the magazine for the Bunnies, there was, it
was like, there were even ears at some point.

Speaker 2 (20:35):
A little cotton tail.

Speaker 1 (20:36):
Yeah, and then maybe, I feel like I'm remembering some
kind of collar thing.

Speaker 7 (20:41):
I think there was a collar with a bow tie.

Speaker 2 (20:43):
That's correct. And an off-the-shoulder, almost kind of like bustier
leotard kind of onesie thing.

Speaker 1 (20:49):
Yep.

Speaker 2 (20:50):
And I believe they're wearing stockings and high heels. Some
of them would have those cigarette carts that they would
carry and, you know, sell cigarettes and get people's drink
orders and stuff.

Speaker 1 (20:58):
Oh, and themed. Sometimes they would change it up a
little bit for the holidays.

Speaker 2 (21:02):
That makes sense.

Speaker 3 (21:03):
Yep.

Speaker 7 (21:03):
You did great. You did great.

Speaker 3 (21:05):
You did great.

Speaker 6 (21:05):
Again, I was never at the Chicago club, so I
only know from the pictures and such. But, yes, so
that was the vibe of this club. Again, with the
bow tie, I guessed. And I'm using quotes around it
because these were just young women. But the rule was

(21:25):
you weren't allowed to touch or date these women. He
was very careful to make it not a quasi strip
club or a quasi like, you know, you're going to
hook up with these girls or anything like that. And
also they wanted to make it, you know. Get as
many women customers in there as well.

Speaker 3 (21:41):
Oh, sure.

Speaker 6 (21:41):
So part of this, and this is interesting. We didn't
go into it. The guy who ran the food and
drink concession for this club and then eventually it became
a circuit was Arnie Morton, who eventually has these famous
steakhouses all across the country.

Speaker 1 (21:56):
Wait, the Morton Steakhouse guy? Yes.

Speaker 3 (21:59):
Yeah.

Speaker 7 (21:59):
Same guy. Same guy. So this is one of his
earliest gigs.

Speaker 6 (22:04):
And they had this crazy pricing plan, which was everything was,
this is when it opened, everything was $ 1.

Speaker 3 (22:10):
50.

Speaker 6 (22:10):
A drink was $ 1.

Speaker 7 (22:12):
50. Your meal was $ 1.

Speaker 3 (22:14):
50.

Speaker 6 (22:14):
A pack of cigarettes and a lighter with the Playboy
logo on it was $ 1.

Speaker 7 (22:19):
50.

Speaker 6 (22:20):
Like that was their kind of thing. And it's like, again,
with Hef, it's a runaway success. Like thousands and thousands
of people are pouring or paying 25 bucks to be
a member. Everyone kind of got accepted. And then could
get part of this sophisticated lifestyle surrounded by these beautiful women.

(22:41):
And part of the experience was there was always two
rooms for show business. And those were usually a singer
and a comic. So this is where Dick Gregory.

Speaker 7 (22:50):
Comes into the picture. Now, at the time.

Speaker 6 (22:59):
It's, you know, Chicago has this big nightclub called the
Chez Paris, which is run by the mob and is
a white nightclub. That was like the big place you
could play in Chicago. So acts from the Chez Paris,
but also play the Playboy Club. And one of these
acts in January 1961, so it's, I guess, 11 months later,

(23:19):
is named Professor Irwin Corey.

Speaker 7 (23:23):
Does that name ring a bell to either of you?

Speaker 1 (23:26):
That's, I gotta be honest.

Speaker 2 (23:27):
Not right off now.

Speaker 1 (23:28):
Not to me. Not right now. Okay.

Speaker 6 (23:30):
He was a very curious kind of almost experimental avant-garde
comedian who pretended to be professor and then would give
lectures on different topics in a very crazed kind of,
do you remember like the way Einstein had his hair
all crazy?

Speaker 1 (23:46):
Yeah. Yeah.

Speaker 6 (23:47):
That was, that was, so Erwin Corey, for some reason
is like, you know, I don't want to work seven
days a week. I don't want to work Monday through Sunday.
Can I get Sunday off? You know, I appreciate this
gig you're giving me here at the Playboy Club, but
I don't want to do it. So Hef, who had
seen Dick Gregory, he was the host of this club

(24:10):
called the Robert Show Club, which is a black club
in Chicago, and said, well, why don't we give this
kid a chance for $ 50? So we hired him that night,
and there were some Southern people in the crowd and
Dick Gregory got there late.

Speaker 7 (24:25):
It was snowing, gets on stage and just kills it.

Speaker 6 (24:28):
Like all of his instincts are 100% correct on how
to handle these crowds, how to talk about race, how
to talk about the fact that he had been in
the South and he did the joke, you know, I
spent four weeks there, one night or that kind of
thing and kills it.

Speaker 7 (24:45):
And then immediately like, oh, let's hire this guy.

Speaker 6 (24:48):
And in a way, that's the first time African-American comedian
had been hired in a white nightclub with a couple exceptions.
But that, yeah, but that was a big thing. But
there's more to the story. Can I keep going?

Speaker 7 (25:00):
Oh, please, please.

Speaker 1 (25:01):
We're on the edge of our seat here, actually.

Speaker 6 (25:04):
So Dick Gregory starts, you know, he had never heard
of making $ 50 a night times seven. Like that was
like out of the, it was mind blowing to him
that he could be making this much money doing comedy.
And word spreads quickly about this kid who, who is
doing great at the Playboy Club. So the New York
Times luckily writes a review of it and then Time Magazine.

(25:28):
And this is where the story gets really interesting to me.
Dick Gregory's dream was to be on The Tonight Show
with Jack Parr. That was the big break, that he
was the Carson before Carson.

Speaker 2 (25:41):
Of course.

Speaker 6 (25:42):
So he was friends with this singer named Billy Eckstein,
another guy you're not going to know.

Speaker 1 (25:48):
But- All right.

Speaker 6 (25:50):
A famous 40s, 50s singer. And Billy was like, I
don't know if you noticed this. Whenever there's a black
comedian on Jack Parr, he lets them do their act.
And that would usually be like an impression. It's like
he had George Kirby on that kind of thing. But
he would never bring him over to the couch to
sit down like he's just a normal American comedian.

Speaker 2 (26:13):
Well, in general, getting brought over to the couch is
the dream of any comic doing the late show, doing
a late show like that. Yeah, yeah.

Speaker 7 (26:19):
No question. No question. No question.

Speaker 6 (26:21):
But when this Time magazine article hits, Jack Parr, producer,
calls Dick Gregory and is like, we'd love to have
you on the show. And he's like, I'm not going
to do the show unless you let me sit down
and talk to Jack Parr.

Speaker 7 (26:35):
Because he had never even thought of this.

Speaker 6 (26:38):
He never realized until Billy Eckstein pointed it out to him.
that this was a thing that Jack Parr was doing,
whether consciously or unconsciously. So the producer was like, well,
you know, that's not the way it works.

Speaker 7 (26:51):
You do a set.

Speaker 6 (26:51):
If it goes well, you might come back and do
another set. He's like, well, then I'm not doing your show.
And then apparently a couple, a day later, the producer's like, fine,
you can do the show and we'll talk to you.
And so, Again, I keep going back to this emotional
IQ of how to handle this situation and parlaying what little–

(27:11):
I mean, you can imagine. He's just playing the Playboy Club.
What little power he had to get what he wanted,
and that was also a breakthrough moment. And then he
became like a hero, and that's the moment. That's why
we're talking to you right now, like that moment. And
then everything changed from there.

Speaker 1 (27:31):
I have a question before because, yes, everything changes from there.
But there's one question I wanted to clarify here, especially
with the tonight show with Jack Parr. It sounds like
there was an emotional calculation on his part or at
least some very clever diplomacy because didn't they invite him

(27:53):
more than once and eventually like, parr finally called him
right that's that's the thing that got me about it because.

Speaker 6 (28:00):
Oh is there more to that that might be right
you're saying that that before like parr just wanting him
on the show eventually parr calls him personally and he
says to jack parr who we idolized i'm not going
to do the show unless you have me on is
that correct.

Speaker 1 (28:13):
That's what that's what uh that's what i had heard
i wanted to see that source because to me if
that's if that's what happens what's fascinating about that is
that it gets to a point where it's kind of
leveraging maybe the ego of the host of the show,
because they're like, you know, I'm this huge show. What
this guy's too good. What gives, you know?

Speaker 7 (28:35):
Yeah. I, I, you know, I will look into that.

Speaker 6 (28:37):
Cause I did, we didn't go into, we just more,
we're talking about the club, but, and I do know
that he turned down the show. I don't remember the
jackpot himself call, but that could be absolutely correct. And
if that is, I mean, there's also, if you think
about it, there was like this thing about black people

(28:58):
and being pushy and uppity and all like that was
like a way to like marginalize a lot of those guys.
So I like that he was willing to risk that,
all of that to sit.

Speaker 7 (29:11):
Down on the couch with Paul.

Speaker 6 (29:12):
And Paul ended up loving him and having on the
show numerous times. And that, as we like to say
on our show, blew open the gates to- having African-Americans
not only on the show, but older African-Americans finally getting
a shot on television and stuff.

Speaker 2 (29:30):
Well, we've heard Dick Gregory later in his life describing
this period, but we haven't heard any of his comedy.
And I think we should hear a little moment of
one of the bits. that might have been something he
would have performed on the Jack Parr show.

Speaker 3 (29:44):
You know, I feel so sorry for Willie. I hate
to see any baseball player having troubles, but that's a great.

Speaker 4 (29:50):
Sport for my people.

Speaker 3 (29:51):
That is the only sport in the world where a
Negro can shake a stick at a white man and
won't start no ride. LAUGHTER Of course, now, don't get
me wrong now.

Speaker 2 (30:03):
We're doing all right.

Speaker 3 (30:05):
Now, at the rate we're going 10 years from now,
you might have to be my color to get a job.
If you get me right, I'll get in there and
raise taxes on you. I mean, now, don't get me wrong.
I wouldn't mind paying my income tax if I knew
it was going to a friendly country. And we have
a lot of racial prejudice up north, but we're so
clever with it. Take my hometown, Chicago. I mean, you

(30:28):
can't see it just.

Speaker 2 (30:29):
Going in there.

Speaker 3 (30:30):
When Negroes in Chicago move into one large area and
it looks like we might control the votes, they don't
say anything to us. They have a slum clearance. You
do the same thing on the West Coast, but you
call it freeways.

Speaker 1 (30:46):
So what we've done here so far is trace this
guy's evolution to the gates. And then when they were
blown open, as you said, he could have, if we
want to speculate— he could have done what some people
decide to do when they're successful in entertainment and just
stayed in that lane and just, you know, worked on
comedy and honed his craft and then eventually, you know,

(31:08):
retired or just exclusively gone on to do Comedy Central
roast or something. But he took it a step further.
And you mentioned this earlier, Wayne, when you say everything changed.
So what changed exactly? What was Dick Gregory's next phase
in life?

Speaker 7 (31:26):
Well, Two things.

Speaker 6 (31:27):
When I say that everything changed, I meant that everything
changed in stand up in that now Americans, club owners,
TV bookers were interested in the voices of African-American comedians.
That's what I meant by everything changed. So you now
had like suddenly Nipsey Russell is on television a lot

(31:48):
more and, you know, Slappy White and these older comedians
like Moms Mabley and Pig Meat Markham. like suddenly they
have a resurgence because people are kind of curious about
this world of comedy. And there's, you know, this underground
world of dirty records with, you know, Red Fox and
Lawanda Page and all of those people.

Speaker 7 (32:09):
So it's just, it's.

Speaker 6 (32:10):
Like kind of like if you go to the African-American
Museum at the Smithsonian and they show you the clips
of the comedians from that era, they're all post-1960. Like
they're all post-1961 when he broke through. Like they're all,
and a lot of people were getting sets and jobs.
So it was just a, it was a bit of a,

(32:30):
a great kind of resurgence. And then through those doors
walks Flip Wilson and Bill Cosby. And then Richard Pryor,
Richard Pryor makes his television debut in 1964. That's only
three years after this moment. It's like, it's a real like, okay,
now we're on, everything's changed and comedians and audiences are

(32:52):
ready to accept as Dick Gregory liked to say, Just
one person talking flat footed on stage to a white crowd.

Speaker 1 (33:02):
And then what were like he continued to work as
a comic, right? To great acclaim.

Speaker 6 (33:08):
He was suddenly making a lot of money. He hired
a couple of writers to help him create more material
because he was really in demand. He put out records.
He's like he's a thing. Dick Gregory is a thing.
And then he gets very involved with the civil rights movement. movement,
which don't forget, I mean, this is before the Voting

(33:28):
Rights Act and before the Housing Act and all of that.
So this is before Martin Luther King in 1963 makes
the big speech. So he starts marching with Martin Luther
King and making speeches and raising money. And what happens
is he starts canceling nightclub dates and basically says, like, look,

(33:51):
I can do these jokes and I can do these
jokes these guys wrote for me and this is all great,
but there's a bigger wave that I'm involved with now.
And that basically kind of like marginalized his standup act
and made him this civil rights icon at the time.
So we basically canceled tens of thousands of dollars worth

(34:11):
of gigs so he could be involved with this movement
and would talk about it. And then he became sort
of identified with that and Because he was doing that,
opened the door again for like the Cosbys and Flip
Wilson and, you.

Speaker 7 (34:27):
Know, Pryor and all of those gentlemen.

Speaker 2 (34:29):
But then he essentially, you know, so those floodgates were open.
All those folks stepped in to kind of fill that vacuum.
And then he kind of walked away from this career
in a lot of ways. I mean, maybe not entirely,
but he clearly had bigger fish to fry. He had
higher priorities, a higher calling, you could say.

Speaker 7 (34:46):
No question. No question.

Speaker 6 (34:47):
And that really motivated him very much. And then I
think in a way it hurt his career, his standup career.

Speaker 7 (34:53):
And I also, for some reason, I just don't.

Speaker 6 (34:56):
Know if he was that dedicated to standup once he
had sort of cracked this code and was like, okay,
I can do this and I can release these albums.
I can make hundreds of thousands of dollars a year
and where I used to make, you know, $ 5.

Speaker 7 (35:12):
Doing this, this gig.

Speaker 6 (35:14):
And yeah, He just– he was very much motivated in
racial equality, which is– I could understand that, which I'm
sure what he had to endure growing up in that
time period.

Speaker 1 (35:30):
We followed some of his work in this field, in
the civil rights movement. He also was advocating for the
rights of Native Americans and for gender equality, which We
found a couple of stories. One that really stood out
was he even got the attention of J. Edgar Hoover

(35:52):
at one point when he ran for president in 1968,
which I had no idea he actually ran for president.
But the rumor is from documents that came out later
that J. Edgar Hoover considered Dick Gregory such a threat
that he ordered the Chicago office of the FBI to

(36:12):
contact the mob to neutralize.

Speaker 2 (36:16):
Yeah, quote-unquote neutralize, whatever that means.

Speaker 1 (36:20):
Yeah, maybe it's something less sinister, to neutralize him during
that race. And I guess I wanted to ask you,
given what you said earlier about the biggest comedy club
or white nightclub in Chicago being run by the mob,
was the mob still really active in Chicago and the

(36:40):
comedy scene in the 60s?

Speaker 4 (36:43):
Yeah.

Speaker 6 (36:43):
I mean, it was starting to fade away a little
bit as these other rooms opened up. But basically, the
nightclub era, which started right after the end of Prohibition
and vaudeville dropping, a lot of nightclubs across the United States, South, North, Southwest, Northwest,
were mob-run organizations. One of the most famous in New

(37:04):
York was a room called the Copacabana, which you see
in these– Scorsese movies all the time but that was
they had the biggest headliners Martin Lewis and those guys
would perform there Sammy Davis with the Wilmaston trio and
those dudes were all mob run and then mob ran
obviously Las Vegas and then had their hooks deeply into

(37:29):
uh Miami which was also this big scene I mean
I guess the only place the mob didn't really run
too much was the uh the Borscht Belt up in
the mountains of the Adirondacks, upstate New York, where kind
of like Jewish comedians were performed there during the summers.

Speaker 2 (37:46):
Let's move on really quickly to a very important event
in the Freedom Summer or the 1964 Freedom Summer in Mississippi,
where all these marches took place. This is a very
big kind of high watermark point for the civil rights movement.
There is a bombing of a church called the Mount
Zion Church, and three young men are sent to investigate it. Goodman, Cheney,

(38:09):
and Schwerner, and they do not come back alive. They
are murdered by members of the Ku Klux Klan and
Deputy Sheriff Cecil Ray Price. This is all proven, who
is also a Klansman. And basically, Dick Gregory goes there,
confronts the sheriff, and sticks his finger in his face
and says, I know you did this, and we're going

(38:29):
to pin it on you. And he reaches out to
Hugh Hefner, who puts up $ 25, 000 of 1964 money which
is no chump change for a reward for anyone that
can lead to the arrest or proof that these men
had something to do with it and to find the bodies.
There is conjecture that the FBI already knew where the

(38:51):
bodies were. They just didn't want to create a giant storm.
And so they kept quiet. And essentially, Gregory, with the
help of his friend Hugh Hefner, took these men to
task and everyone essentially, I mean, the degrees to which
they were punished, you could kind of argue were not
nearly fitting the crime, but they were exposed. And that

(39:13):
brings us around to Hefner kind of, I don't know,
you think of him as this kind of impresario of
smut or something like that. But as you said, he
was very interested. He was very progressive. He was all
about literature and good writing. And people joke about, oh,
I only read Playboy for the articles. But there's... a
lot of truth to that. I mean some of the
greatest writers of all time have gotten their start writing

(39:35):
shorts for Playboy or articles or having short stories published.
So it absolutely has a place in that kind of canon. And–
More recently, Dick Gregory, unfortunately, we lost several years ago,
but near the end of his life, he participated in
a roast of Hugh Hefner, and he had a really
interesting quote.

Speaker 1 (39:56):
In 2001, right, during the roast of Hugh Hefner, he
actually went beyond the typical insult stuff, right? And I
think this is what you had mentioned earlier, Wayne, where
he says, You had a courage when no one was
bringing in blacks and minorities and let you stand flat
footed in America and just talk. You brought me in.

(40:18):
You didn't give me a lecture. You gave me no instructions.
I come here tonight not to roast you, but to
say that had you not had the guts back then,
we black comics that the world has been able to
look at and understand our genius, we would be in
some pot roasting in debt, knowing we were never going
to make it. And I have to ask because that's

(40:38):
such a powerful statement.

Speaker 7 (40:40):
It is to this day.

Speaker 1 (40:42):
Yeah. Were they like friends past the business stuff, past
like the giving the start? Because that's a very personal,
sincere statement. Did they interact throughout his career in activism
as well as comedy?

Speaker 7 (40:58):
Well, I know this.

Speaker 6 (41:00):
I know in 1962– When Lenny Bruce got arrested at
the Gate of Horn, which was this little club also
in Chicago that Hef put up his bail money and
just felt like what Bruce is trying to do with language,
I'm trying to do with, you know, with literature here.
Like show, use satire and language and cartoons to sort

(41:25):
of elevate this art, not only the humor, but the
conversation about America in general. So I know he's always
been an activist in that. I don't know how close
they were through the years. I know that there's dozens
of Dick Gregory interviews where he thanks Hugh Hefner for
having the courage to put him on that stage and

(41:47):
or the foresight to put him on that stage. So
I know he was like extremely grateful. Obviously, what happens is,
I hate to say this, the Playboy clubs were basically
like Dick Gregory immediately got bigger than the Playboy clubs,
which became this circuit. There was like 20 of them
all over the United States.

Speaker 7 (42:06):
Phoenix, St. Louis, you know.

Speaker 6 (42:08):
So Miami, New Orleans, Boston, New York. So he was
already too big to play the Playboy circuit. So I
don't know if that was a thing between the two
of them.

Speaker 7 (42:20):
I'm not sure.

Speaker 6 (42:21):
But I've heard Dick Gregory numerous times thank Hugh Hefner
for that moment.

Speaker 2 (42:28):
Yeah, absolutely. I mean, he really did kind of go
out on a limb when he, you know, he did
kind of have the world, you know, on a platter
at that point because of, like you said, the Playboy
magazine just printing money and kind of having a sense
that he was untouchable. And that's really important. But also
any other person could have done something completely different with
that kind of success and that kind of power. And
he instead took a chance and went out on a

(42:49):
limb when he didn't have to. And without that moment,
Dick Gregory wouldn't have had the platform to affect such
social change that he did, not to mention blowing the
doors wide open for black comics, you know, around the world.

Speaker 1 (43:02):
Yeah.

Speaker 6 (43:02):
It's a, it's an incredible story and it all happens
in this, you know, in this little club in Chicago,
in the middle of winter, January, 1961, there's a snow
storm and these takes a bus to the gig and
he gets off on the wrong stop. The whole story
is just crap. So he's running through the snow and
he's slipping and he's never been to the playboy club.

(43:24):
So he doesn't know exactly where it is. And then
he gets there and yeah, he gets on stage and
does his thing. As you just reflect on like his
use of language and the casualness of his performance. And
he is just like, this is his moment.

Speaker 7 (43:43):
And he absolutely embraces it.

Speaker 1 (43:47):
And speaking of speaking of thanking and speaking of moments,
you know, we can we can thank Hugh Hefner the
way that Dick Gregory did. But we also have to admit,
you know, this wouldn't have been near as big a
moment had Dick Gregory not been such a talented writer,
performer and comic. So I don't want to get away

(44:08):
from how just objectively good the guy is.

Speaker 2 (44:11):
And also so savvy. I think it's not to be
overlooked that he wasn't rolling over when he kind of
did these maybe a little bit more palatable performances for
white audiences. he was being smart. He was reading the
room in a way that was able to like keep
him in the game. And, you know, as his comedy progressed,

(44:32):
I guess, or as his career progressed and he was
able to take more risks, you know, he was very
outspoken about race and politics and all of that, even
in his acts.

Speaker 7 (44:41):
No question.

Speaker 6 (44:42):
Again, it goes back to what we were speaking about
earlier about you said savvy. I said, you know, emotional IQ.
Like he just, I felt like he had a, a
really heightened level of like how to play these situations.
And he had seen, if I'm not mistaken, sometimes they
would have like, I don't know if it was Sammy
Davis at this Robert Show Club, and he watched Nipsey

(45:06):
Russell play a crowd. And sometimes they would get white
crowds coming into the Robert Show Club, which was a
black club, but they would let white people in, obviously.
So I think he had seen some other black comedians
like work the room. And he's like, okay, I think
I know how to crack this, this code. I think
I know the combination, uh, that, that'll, that'll make it work.

Speaker 1 (45:30):
So this, this is a watershed pivotal moment, uh, in,
in comedy and in American society overall, uh, you know,
longtime listeners know one thing that, uh, that I never
shy away from a Noel. I don't think you shy
away from it either. is admitting when we need to

(45:52):
know more about something. So thank you so much, Wayne Fetterman,
for introducing not just us, but our audience to Dick
Gregory and talking to us, even though you established pretty
early on in today's episode that you would always rather
be talking to Casey.

Speaker 2 (46:09):
That's fair. We feel the same way. Trust me. I
want to really quick, I just tell a very, very
short story. I, uh, had an interesting privilege to– I
was a reporter for public radio when I lived in Augusta, Georgia,
and I got to cover the funeral of James Brown.
And Dick Gregory actually spoke and gave a eulogy at

(46:29):
James Brown's funeral, and I was not aware of him,
and that was the very first time I had ever
heard of this man. And I really thought of him
much more– all the research I did, which wasn't much,
that he was much more of an activist. So hearing
this completed part of his story– It's really fascinating. But
he gave a really powerful speech at James Brown's funeral.
It was really interesting to see him kind of in

(46:50):
the flesh and a really fascinating man. Very, very glad
to know more about him. So thank you, Wayne, for
hipping us to this story.

Speaker 7 (46:58):
Well, you know, I'm just– you're welcome.

Speaker 1 (47:03):
So, Wayne, at this point, people have heard us mention
your podcast that you do with your co-host, Andrew Stephen.
I just want to let everybody know that the history
of Stand Up Season 2 is coming out now as
we speak. It hasn't all been released yet, though, right?

Speaker 7 (47:24):
That is correct.

Speaker 6 (47:25):
We are still editing, interviewing people, putting things together for
this season.

Speaker 1 (47:31):
So the last episode I listened to, if you're interested
in hearing more about the Playboy circuit, is Season 2,
Episode 2, which came out just a few days ago.
as we record this, and it explores the story of
Hugh Hefner and Playboy magazine and how they became, this

(47:52):
is a quote here from your show, Wayne, how they
became unlikely champions for an era of comedy between nightclubs
and the comedy boom.

Speaker 7 (48:00):
That's exactly, I can't believe I came up with something
that articulate.

Speaker 3 (48:03):
That's great.

Speaker 7 (48:04):
That's very succinct.

Speaker 1 (48:05):
You've done good.

Speaker 2 (48:06):
You've done good, Wayne. It's a great show. Where can
folks find that? What's the best way to pull that up? I.

Speaker 6 (48:13):
The classic, wherever you get your podcast, whether it's, you know,
on iTunes or Stitcher.

Speaker 7 (48:20):
I'm not sure, whatever. It's, it's everywhere.

Speaker 2 (48:22):
It's there. It's out there.

Speaker 7 (48:24):
Yeah. Yeah. It's easy to get. It's easy to get.

Speaker 6 (48:27):
And thank you very much for, listening to it. I, um,
you know, I, this is a, I'm passionate about this,
but I, I just don't know how many people are
really interested in the history of standup as opposed to
standups now, you know, that, you know, talk about their
careers and stuff.

Speaker 1 (48:43):
I've actually, I've been keeping note here. I'll, I'll confess
there were a couple of older comics that you had
mentioned in the course of today's episode where I was
writing them down. I was like, Oh wait, I've got
to look that guy up. I got to see if
I can hear something. So I've got some homework today
and I'll probably be posting some stuff about this on

(49:04):
our own Ridiculous History Facebook page or Instagram. You can
find us there. You can also find us on Twitter. Wayne,
I'm going to volunteer you. It looks like you are
also available on Twitter at Fetterman.

Speaker 3 (49:17):
Correct.

Speaker 2 (49:18):
And if you want to find me, and Ben individually,
we keep up a pretty decent Instagram profile. I am
at HowNowNoelBrown.

Speaker 1 (49:26):
And you can see me getting kicked into and out
of various countries at Ben Bolin. Yeah, that's true. That's true.
Don't make fun of me.

Speaker 7 (49:33):
I love it.

Speaker 4 (49:33):
I love it.

Speaker 1 (49:35):
So that is our show, everyone. Thank you so much
for tuning in. We'd love to hear your take in
some of your favorite comics throughout history, right?

Speaker 2 (49:44):
Absolutely. Thanks to super producer Casey Pegram. Thanks to Alex Williams,
who composed our theme. Big thanks to Christopher Haciotis, who
is here in spirit. and Jonathan Strickland, who, you know,
he can take a long walk off a short pier.

Speaker 1 (49:58):
Big thanks to Jonathan Strickland, a.k.a. The Quizster. I know
you and I don't see eye to eye on that.
And big thanks to Wayne, and thank you so much, folks,
for listening.

Speaker 2 (50:07):
We'll see you next time. For more podcasts from iHeart Radio,
visit the iHeart Radio app, Apple Podcasts, or wherever you
listen to your favorite shows.

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