Inside Conan: An Important Hollywood Podcast - Pete Holmes Revisits His Foray Into Late Night Television
Episode Date: May 31, 2023Actor, comedian, and author Pete Holmes joins Mike and Jessie to discuss Conan plucking him from obscurity and donning him with a his own Late Night talk show, much like Lorne Michaels did for Conan i...n 1993 and how that opportunity led to his meeting of Judd Apatow and the eventual hit HBO series Crashing. Got a question for Inside Conan? Call our voicemail: (323) 209-1079 or e-mail us at insideconanpod@gmail.com.Â
Transcript
Discussion (0)
And now, it's time for Inside Conan, an important Hollywood podcast.
Hi, and welcome to Inside Conan, colon, an important Hollywood podcast.
I'm one of your hosts. I'm Jesse Gaskell
here with Mike Sweeney.
I'm one of the other hosts.
That's me.
Yeah, that's you.
Right.
And yeah,
and we're co-hosts.
Yes.
Where two people
do the work of one
or half a person,
a quarter person,
but we do it, damn it.
Yes, we do it.
We do it in style.
Yeah, we sure do. I mean,
if you could see how we're dressed right now, that style is the word. We're allowed to wear
whatever we want because we are on strike. Right. But you're not allowed to point it out.
That's. We are on strike. And what a segue into. Yes. Our current state of affairs yeah yeah yeah we're on strike
yeah the writers guild that is have you been in unions prior to this prior to the wga no no no
yeah in in your work history okay no i've been in unions but i never yeah you were in the mailman's
union i was in the mailman's union i was in the amalgamated Meat Cutters Union. Really? What is that? I was a deli worker at A&P.
Oh, my God.
There's a union?
Of course.
Amalgamated Meat.
It's called the Amalgamated Meat Cutters Union, which I just love that name.
Is the meat amalgamated or the union is amalgamated?
Head cheese.
Okay.
It qualifies.
Yeah.
And then when I was a stand-up comic, they tried to unionize.
Oh, my God.
In New York.
And they formed.
Oh, that's kind of hilarious.
And they had a meeting.
I went to the meeting.
It was just bad comics trying out their material.
And that's when I learned.
I literally was like, I will never go to another meeting.
Yeah.
A union meeting.
So, yeah, we're hoping this strike gets wrapped up quickly
and in our favor of course yes whatever that whatever that means i i think wrapping it up
would be in our favor yeah i think we'll get to that point sure pretty quickly yeah um do you
write i don't write slogans on my signs oh god i. I don't. I did. I did end up writing one, but I really, I stressed about it because I, you know, it's,
it's basically your calling card and people have been Instagramming all the funny signs.
And I've seen a lot of funny ones that made me laugh.
Yeah.
So I just felt a lot of pressure to be hilarious.
But then I thought there's nothing worse than trying to be funny and coming up short.
So I ended up not really going
with a funny one.
Yeah, yeah, yeah.
More poignant one.
Oh, very nice.
Yeah.
Good for you.
If you see me out there,
you'll see my sign.
Do you write up a new one every time?
No.
Do you take it with you?
But I might have.
Yeah, I took it with me.
Is that true?
I like it.
Okay. Yeah. Just to have it because otherwise you end up with you? But I might have. Yeah, I took it with me. Is that true? I like it. Okay.
Yeah.
Just to have it
because otherwise you end up,
you start the day
and you have to look for a sign
that someone else has written
and you have to decide.
You could spend hours
just looking through all the signs.
That's what I did.
I like, I'm going through.
I feel like it's a bargain bin of like.
Yeah.
And they're there.
Yeah.
Road records.
Yeah.
There's some bad ones.
And yeah,
and you don't want to, you don't want to hold a sign that's not you no no i i feel like a bad sign is only
going to prolong the strike they're going to be like hey wait a minute oh this is the kind of
writing you're doing exactly i know uh anyway this season yeah we if you're still with us
we are covering conan on Road. And that means Conan,
that's outside Conan. Anytime Conan stepped away from the desk to go on a remote or do a travel
show. Bathroom break, anything. Anything. We are discussing. We've got it. And today we're joined
by the hilarious, this is extremely outside Conan, Pete Holmes. Pete Holmes is hilarious.
And he had a really funny talk show.
He did.
On TBS.
That was filmed in the Conan studio, but it was not Conan.
So I feel like that counts.
Yeah, it was shot right next door.
And it was produced by Conan and Jeff Ross.
Yeah.
So a lot of people from our show helped get that show up on its feet.
Yeah.
So here's Pete Holmes.
Here's your cold open.
Okay.
Okay.
Thank God.
For three seasons, we've been looking for one.
I feel great about being Conan O'Brien.
Good, good, good.
Oh, no, that's not the
podcaster.
Oh, I'm so sorry.
I know Mike White. Did you think
Conan was going to be here?
I never heard that on a podcast. I know Mike White!
I was on The Amazing Race with him.
Who says that? I meant not Mike White.
Who's in The White Stripes?
Oh, Jack White.
There's a Jack White, there's a Jack Black,
and there's a Mike White.
You clearly don't know Jack. You don't even know Jack White's name.
I don't know my whites.
I don't know my whites.
I don't see color.
They have their time.
Yes.
They have their time.
It's over.
And I'm into the...
Say the three white people
talking together.
Talking about nothing
and being recorded.
We're like Hitler
in his bunker.
It's the last days. It does feel true. For these three white people. Yes. Oh, we are recording. Yeah, like Hitler in his bunker at Celestis.
It does feel true.
For these three white people.
Yes.
Oh, we are recording.
Yeah, yeah, yeah.
Oh, yeah.
We're not ashamed
of anything we're saying.
I, I, I, I.
Yeah.
Here's a cold open.
Yes.
What's our podcast?
You've never brought in
Leon the Professional.
That's me.
And you guys are
Natalie Portman
and you're 12.
Is it appropriate
that I'm a hitman
and I took you under my wing?
In the 90s, it was fine.
It was fine.
Absolutely cool.
It was fine.
It's called mentoring.
It's called older mentoring.
Yeah.
But look at her now.
Nothing is okay.
That was okay in the 90s?
Yeah.
Yeah.
Finished your sandwich.
Right.
When did we all start saying we finish each other's sandwiches and we're like, but now
it's the new phrase.
Oh, is it?
It was a joke.
It was on Arrested Development, wasn't it?
It was on Arrested Development.
And so were a lot of things.
You're saying it's not a new phrase.
But it's bled into the vernac.
Here's your cold open.
My father, if you give him a gift, he takes it as an assault.
Like if you, because he will be like he doesn't.
Even on his birthday?
You give him,
give me these lentils
and I'll be my father.
Pete, can I offer you?
No, Pete's dad.
Okay.
How do I know
you're not Pete Jr.?
I don't know
your fucking dad's name.
My name is Jay.
Oh, Jay.
Okay.
All right.
All right.
Jay,
I went out on a limb
and got you a bag of lentils.
Half-eaten lentils.
I just assumed you were Jay. got you a bag of lentils. Half-eaten lentils.
I just assumed you were going to-
Oh, just exactly what I wanted.
He has to immediately put it down and cut your legs out.
Yeah.
Because it's too vulnerable.
He's so old school that if he was like-
Thank you.
Sweetie, I love pink Himalayan salt.
Like, that would be too much vulnerability.
It would.
Pretty gay.
Also, he doesn't know me.
He doesn't accept a gift.
He knows you.
Well, that's our cold open.
He reads the credits.
Are you mocking?
No!
It was a fine cold open.
Thank you.
It's cold.
Oh, a cold open.
It's cold.
Pete, just what I was hoping for.
It's cold.
Thanks, Pete. A great cold open. It's cold. Oh, a cold open. It's cold. Pete, just what I was hoping for. It's cold. Thanks, Pete.
A great cold open.
It was a good, it was a, it wasn't.
Roll that theme music.
It was a good cold open.
We should do cold opens from now on.
Do you not do a cold open?
You don't do like a little taste?
Do you do a cold open on your podcast?
Yeah.
We just started doing a little taste.
Just a little taste.
Yeah, what prompted that?
Was that a note or you just.
A note.
I listen to other people's podcast,
just like all of show business.
I just heard it on someone else's podcast
and I was like,
that gives a little taste of where it's going.
A little teaser.
I listen to someone else's podcast today
to prep for that person being on my podcast.
Sure.
The whole world is just podcast, podcast, podcast.
It's a verb, it's a noun, it's a place, it's, podcast. It's a verb. It's a noun.
It's a place.
It's a job.
It's a calling.
It's a passion.
Soon a building.
A state of mind.
And now it's a building.
Right, right, right.
But I was listening to you on their cold open.
Oh, I should tell you what show it was because that would be nice to them.
Yeah, let's get them on.
Let's get another podcast.
Now we're plugging other podcasts.
It was called the DOAC podcast, Diary of a CEO.
Oh.
Oh.
He does a cold open.
This motherfucker.
No wonder he's a CEO.
He opens with four minutes of cold open.
What?
Just the best snippets of the entire episode.
That you're about to hear.
Before any ad.
There was no ad.
Before any welcome to SiriusXM, nothing.
Just pow, pow, pow, pow, pow,
pow, pow, pow. And I was like,
that was incredible.
You know when you see someone else doing what you do
but with like effort? Professionally.
And a
plum. And you're like,
oh, like you're embarrassed.
Like you're suddenly,
you widen at the buffet.
I'm in a wet bathing suit at the buffet.
You widen and there's chandeliers
and white tuxedos
and everyone's like,
I'm a woman with a monocle goes,
he can't, you know?
And I'm just like,
what?
I swam up.
Or if you're like me,
you just assume he's doing it to show me up.
It's like this motherfucker.
Ah, you're like my dad. What are show me up. It's like this motherfucker. Ah, you like my dad.
What are you thinking about?
That's exactly what I wanted.
Is that his name? Jay.
John. John. John Holmes.
John Holmes. John. In our family, we
called him Shorty. Ah.
Sorry, John Holmes. See, you're too
pure
or young. Oh, I thought that was a John Holmes
of porno actor. Oh, he's a porno actor. Oh. Does he have a short penis? No, I thought there was a John Holmes porno actor.
Oh, he's a porno actor. Oh.
Does he have a short penis?
No, he has a huge,
huge ding-dong.
Huge but short?
No, no, no.
We go,
growing up in my family,
so my dad's name is John Holmes.
Yeah.
My brother's name is John Holmes.
We got a lot of crank calls.
Back in the day,
you crank the call
and you'd just go
in the phone book
looking for names
of porn stars.
Yeah, yeah. You'd call Mrs. Whitehead and she'd be like, yeah, when are you gonna pop? You crank the call and you just go in the phone book looking for names of porn stars.
You call Mrs. Whitehead.
Yeah, when are you going to pop?
We call Bruce Wayne and we go, Wayne, it's the Joker.
And if you want to see Robin again, we've got him down at the warehouse.
And they were like, yeah, yeah, yeah.
Oh, boy.
Let me put you on hold.
I'm on another Bruce Wayne prank call.
Thank you so much for this humorous prank call.
Well, we appreciate the attempt at levity.
We also ask you to respect
our residential...
My mother has lupus.
That's the whole thing.
The phone frightens the dog.
And while, yes,
your take was unique
and refreshing.
Now you have to text them,
you know?
It's not the same
texting Bruce Wayans. No, you have to bet they're hard know? It's not the same texting Bruce Wayne.
No, you have to bet they're hard to track
down as well. What was I saying?
John, you're growing up. Oh, so they're both
named this huge wiener
porn star.
Boogie Nights
is based on John Holmes.
So we would get these phone calls
and they'd ask for John Holmes and they'd be snickering
and laughing. So the family joke was that my father,
who would sometimes take these calls,
would go like,
in our family, we call him Shorty.
So the joke that I grew up in
from like six years old was like,
we have bigger dicks than John Holmes.
Yeah.
Which I'm not complaining.
No.
Like you'd think I'd be like, that's weird.
I was like, my family to this day
even though I grew up religious
and a little bit uptight in certain areas
like jokes were always okay
here's an example
my mom
she's like
your father called me a bitch and I go were you being a bitch
and she laughs so hard
my dad morbid jokes.
Like you can be like,
well, I'll see you next time.
And he'll be like, well,
and I'm like, yeah, unless you die.
And like, everybody's like,
I'm just like,
I wouldn't say I talk shit about my family.
I'm just, I'm one of those mopey.
Like I like feelings.
I like going into the dark corners of my psyche.
I'm going to say something
very positive about my family.
We love jokes.
And like way before it was cool or like normal, I'm going to say something very positive about my family. We love jokes.
And like way before it was cool or like normal,
we had the like, if it's funny, it's okay.
And even on crashing the show I did,
I had them sign a release because the lawyers wanted me to sign,
get them to sign a release.
And they didn't care at all.
They were honored to be mocked on our show.
I know, yeah.
So you don't have,
because I know a lot of comedians,
especially that have a thing
where they're like,
I have to wait until my family's dead
to be able to talk about certain things.
A lot of people.
Yeah.
I know a lot of people.
I know a lot of,
I feel like that's too dark,
but there are a lot of people
that are waiting for sexual revelations.
Oh, yeah.
And that's a tragedy.
That's a tragedy.
But my family would,
I don't know how that'd be if I was gay,
but they would have to fucking deal with it.
I'll tell you right now.
Yeah.
I would love to break their hearts.
Not break their hearts,
but I'd love to just rock their boat.
Just say anything.
Yeah, you could do it.
I know.
You could do it.
I know.
I wonder how they would take it.
Just for fun.
My dad would be like,
come on, get out of here.
Just exactly what I want.
It's a bit, right?
It's a bit?
You call them bits?
He knows the bits knows you're doing this
just to spite me
he knows the bits
so when you were six
yeah
big dick joke
did you
did they explain
about who
John Holmes was
and
yeah I don't
or you just
understood it
instinctively
yeah you heard it
he also died of HIV
right
HIV
oh
so I knew that too.
Wow.
So when it was explained to me,
there was a big ding-dong porno star
who was very coked up
and tried to break into the mainstream of movies.
And he was also one of the first,
I think, notable or known people.
Yes.
He'd get HIV.
And that sort of began the thing.
But I also think that didn't help the,
I don't know if it was part of the stigma.
It probably ruined the prank calls.
It's helping the podcast.
It's helping the podcast.
HIV, AIDS, people want to hear about this.
Sure, they do.
On a college podcast.
We usually always segue into 9-11.
Yeah, we do.
But it's kind of-
Hitler in the bunker.
Yeah.
Why was he in the bunker, sweetie?
What had just happened?
Oh, it's okay to skate on the thin ice, but I can't jump in the water?
I think an army was invading his beloved Berlin.
So he went under Berlin.
Well, hey, Pete, I hate to lay tracks for this train.
Lay tracks.
I'm so sorry.
Because I honestly don't know.
How did you come to be in the Conan cinematic universe?
How did you get your... I don't know that either.
Your talk show.
You actually caught the UV blocking umbrella that he keeps his whole staff under.
He goes, we'll be safe under here.
Okay.
I was doing stand-up
comedy and I wanted
to be on Conan by the time I was 30.
That was my goal. Oh, that was actually, you
had kind of written that out. I had,
what if I ruined the podcast?
I manifested it.
Just everything sucks. The whole rest
of this thing sucks.
I believe in positive vibes
and I believe in setting intentions.
I like to say,
you don't get everything you manifest,
but you did manifest everything you get,
if that makes sense.
Meaning, you do hit what you aim for.
You don't always hit it,
but if you hit it,
good chance you were probably aiming for it
on some level.
Yeah.
So I did set my sights on doing Conan.
Cool.
I didn't really watch him very much
until I moved to Chicago, which is when I started doing stand- Cool. I didn't really watch him very much until I moved to Chicago,
which is when I started
doing stand-up
when I was 22.
I had been doing it
for a couple years,
but I got serious
when I was 22.
Okay.
I'm just curious.
What year is it?
No, I don't care
how old you are.
It's your favorite year,
2001.
Any riffs on 2001?
A clear Tuesday?
Not a cloud in the sky?
Are we getting warm?
You knew exactly what I meant.
Where were you doing stand-up for two years prior to moving to Chicago?
Barely in Boston.
Okay.
Barely.
I imagine that's a hard time to break in.
It was. And I just didn't know what I imagine that's a hard time to break in. It was.
And I didn't know, I just didn't know what cocaine was.
And you didn't talk fast enough.
I'm not even kidding.
I mean, it's just.
Hilarious.
And I don't mean that in a bad way.
No, I'm not saying like hilarious, like some tough guys are like, that's hilarious.
But they want to fight you.
I mean it like that's hilarious.
I was just so, I was religious and I was sweet.
It's like, just picture Jack McBrayer and I'm going into comedy clubs.
I'd rather not.
Me too.
That guy's a, he's a knife wielding savage.
Also very tan though.
Is he?
I don't care for that.
Okay.
So you're in Boston.
And so what made you move to Chicago?
Did you have friends who were comics who were there
or did you feel like it was suited,
would suit you better or something?
Well, I'd never felt like Boston was going to let me be a grown-up inside of it.
I'm one of those prophet in his hometown people.
Like, I still feel like a child when I go to Boston.
I don't like the feeling it gives me.
If you're not from Boston and you're not from Boston, go to Boston.
You will love it.
I go to Boston and my penis goes inside my body.
I hate it. Like, I can't go back to my high school. It I go to Boston my penis goes inside my body I hate it
like I can't go back
to my high school
it's terrifying to me
even
yeah
so Chicago
but I got a sense
but I wanted to be on SNL
so I was like
what did Chris Farley do
and this is like
very early internet
pre-internet basically
so I'd read books
about Second City
and it basically
sounded like
truth and comedy
all of that.
Yes.
And actually,
Truth in Comedy was a big one
because that was like...
In Truth in Comedy,
it says,
it's very...
In fact,
I call such hard bullshit on this,
but Sharna Halpern is like,
stand-up comedians are like
sad, lonely Arthur Miller salesmen.
They go around and hawk their gags
for pathetic laughs
and then go cry in a holiday inn.
Improvisers.
Not like improv.
They were like, behold the improv.
They made it sound like, let's talk about good mental health.
They made it sound like Mormonism.
They were like, it's a community.
There's game night.
There's free beverages and everyone's yes-anding and it's corporate and communal and beautiful.
Nobody gets paid.
But I totally, exactly.
It's basically, it's a beer drinking group
with an improv habit.
Yeah.
I believe that was an Onion headline.
But I was like, I just needed some guidance
and that's all I had to go on.
And what Farley did was he lived in Madison.
He went to Chicago.
Mike Myers was in Toronto, I believe.
Went to Chicago.
Or maybe he did Second City in Toronto. It doesn't matter. Everybody was doing Second City. Yeah. I was like, I believe went to Chicago like or maybe he did Second City
in Toronto
it doesn't matter
everybody was doing
Second City
yeah
I was like I'm gonna do
Second City
I'm gonna get an SNL
because in college
everybody was like
you should be on SNL
because nobody knows anything
but you're the funny guy
so you're like
you should be on SNL
and I was
the tall
lumbering
improv
not celebrity
but like
the
I'm gonna to own.
I was the standout of my college.
Yeah.
Yeah.
Says the professional comedian of 22 years hesitantly.
You know, I did sort of, I did well.
I did well.
Well, we looked up every member of your college improv team.
They're here now.
That's why these screens are here.
I wasn't the most beloved though. That's why these students are here. I wasn't the most beloved, though.
That's why I hesitated.
It wasn't that I wasn't liked, but some people were just like the favorites socially.
And then the game would start and I'd be like, scoreboard!
But nobody likes that guy.
I wasn't cocky about it.
They were better at being everybody's friend.
And I was very like hyper focused.
Yes.
I was very loud.
And then I got to Chicago and I realized,
like I'd go to a Second City audition or something
and everybody looked like me.
It was all six foot five.
They're all six foot six.
Oh, you know what?
There's a lot of giants.
There are a lot of giants.
Actually, now that you mention it.
Yes.
And we all like looked at each other.
In your same plaid flannel.
We just had different hats.
Like some were cowboy hats,
some were trucker hats,
some were fedoras,
but we were all the same guy.
And we're like, there's only one slot.
So then I realized very quickly,
I moved to an improv city to do improv
and ended up doing standup.
I worked at Bennigan's on 150 South Michigan
in San Juan Walgreens.
But I would walk,
my stop was Irving Park,
Irving Park Brown Line.
So I'd walk past a place
called the Lion's Den
every day on the way
to the train.
And there was a sign,
all it said was Monday comedy.
And then Tuesday,
other things.
But you know,
Monday comedy.
The too much detail guy.
Taco Tuesday.
Wine Wednesday.
Totally unnecessary.
I can't remember for the life
of me what Wednesday was.
Because all you cared about was that
stand-up night on Monday. Tell us
what happened. Yes, can we talk to him?
The guy that saw that side. So I was
so, I was scared. I think I had
a sense that it was a standup night, but I just went in the back just to see the room. Yeah. Not
on a Monday, just to see where it was. And it was this little box. It was actually perfect,
but I didn't know anything about comedy rooms, but I was like, it wasn't very big. I was like,
okay. And I left. And then the smartest thing I did
and sort of the best advice I have
for people that want to do standup.
And then I die.
There's your cold open.
Cold closed.
Cold open number three.
I went and watched.
And that's the best advice I can give
is you're so scared.
You think everyone's going to be so good.
And I was raised by an overloving mother and a withholding father.
And that's a recipe for talent.
That is a recipe.
So I went in.
I was ready to be a comedian, but I was still very scared.
And I went in and I watched.
And I'm not being cocky.
I feel like a lot of people would feel this way.
I was like, I could smoke
all of these fools.
It was terrible.
You said AA meeting.
It is a little bit like
a lot of these people are unstable
or just in a rough spot.
They're just kind of getting up.
And going back to my earlier
point, stand-up wasn't like
I'm not saying it was for dorks or anything but it was a fringe activity. And like going back to my earlier point, stand-up wasn't like, I'm not saying it was for dorks or anything,
but it was a fringe activity.
So like,
we weren't,
you wouldn't watch and go like,
oh, he's doing Seinfeld,
or maybe Seinfeld,
but he didn't have the lexicon that we have now.
So it's just a bunch of people doing bullshit,
some funny people.
And that was the smartest thing I did
because the next week I went and I signed up
and I started doing it. And I had done it in Boston, but that really felt like my start.
Oh, that's great.
Yeah.
And, and so.
And you were immediately good at it and that's the end.
One week later, you had your own show. The trouble with social media and YouTube and all these things, there's that great line in Inside Llewyn Davis where they're like,
Oscar Isaac goes, I never released the early stuff.
It kills the mystique.
And I really think there's a killing of the mystique that happens now.
It's because you start and you start posting your clips immediately.
You don't have that whole learning curve.
You need to be underground for a little bit.
And that's what was awesome about Chicago.
I'm not saying it's underground necessarily anymore.
But before you moved either to New York or LA.
Exactly.
And it was just to be the best person in the scene.
And not even necessarily to make it.
I definitely was like, I'm going to be a comedian.
Full stop.
No joke.
That's what's happening.
And plus there's less pressure probably being there.
There was.
Yeah.
There's other details in the story.
I got very lucky when I was in Chicago.
The few times I opened for somebody,
it was Bill Burr and Jim Gaffigan.
Oh, wow.
Literally the two times my friend Dan Kaufman.
So you really had a community already of people
who either were already doing well.
Yes.
And when I moved to New York,
I got a phone call from Jim Gaffigan
and he was calling to ask me to open for him in Indiana. And I was like And when I moved to New York, I got a phone call from Jim Gaffigan and he was calling
to ask me to open
for him in Indiana.
And I was like,
I just moved to New York.
And he was like,
well, I can't fly you out.
I was like, okay.
So I was like,
ah, fuck,
but at least we were in touch.
I have so many stories.
But that was the other,
the other thing I tell people
that are doing stand-up
is I was like,
don't try to be funnier
than Kevin Hart.
Try to be
one of the funniest people just on the show.
Right.
Just try to shine on just that show.
Yeah.
And that's your mark.
And if you're doing an open mic,
and those days at the Lions,
and 50 people would sign up, it would take hours.
Yeah.
So, you know, if you could be in the top five of those people.
Right.
And you know, what will really give you a leg up
is if you have a coherent
beginning, middle, and end.
If you write your set.
Yeah.
You'll be...
Cold open.
Yeah, if you do a cold open
and a 9-11 and a Holocaust
and an AIDS,
you're in business.
Smooth sailing.
You got bingo.
It's just mop up after that.
If you're not drunk
and if you're not just trying
to say things
you're not allowed to say,
you're way ahead. Yeah. And if you write a beginning and if you're not just trying to say things you're not allowed to say, you're way ahead.
And if you write a beginning and if you study comedy, I don't mean to make it about this,
but like even when I wasn't that funny and I wasn't, nobody is,
I had a beginning and in what I thought might be around the four minute mark,
I'd try to do a callback.
You came back to something.
I'd try because I saw the pros doing that.
And I remember my parents came and told me,
this was actually in Boston.
I can't believe I was okay with them coming to see me.
I still get terrified of that.
But they came in and they watched me and they still talk about this,
that the host of the open mic at the Comedy Connection,
I didn't do that well.
I did okay.
I still remember the routine.
It started talking about free samples
at the food court in the mall.
I remember this is a joke.
I remember I go, food court?
I was a big Seinfeld guy.
What is this?
Where rebel foods go on trial?
Wait for the tag.
I go, you're going to fry for what you did, chicken.
It's terrible.
But I talked about the free samples.
And it was this whole like-
This is the reason you had to move to Chicago.
Oh my God.
I had to run from my past.
After that.
The routine was,
I don't think I've ever really talked about this.
Not that it's hot take,
but when you do your own podcast,
you get excited when you're like,
I think I found something.
Something I've never said out loud before.
Something new.
You guys know.
You guys know the thrill I'm talking about.
But I,
it was talking about
that you would
take a free sample
it was always general
in Boston you call it
general gow's chicken
general so's chicken
I believe
most of the world calls it
one drunk guy
at a Red Sox game
said gow's
and you're like
I think it's
what the fuck
you're saying to me
and it was just gow's
it's now gow's
oh are you from China
yeah
oh you're from China you you from China? Yeah.
Oh, you're from China.
You're from China.
And you come right to Fenway.
Like, where do you get the G in that word?
It's TSO.
Anyway, I got to go through gal pre-check.
Gal.
That was a stretch.
That was a stretch.
I know what you were doing.
And I love, that's all I need.
In comedy, if you know what I was going for,
still a B minus.
I talked about how you would take a sample.
You just have nothing to talk about.
I'm 20, 21 years old.
You have nothing to talk about.
You just need something. I haven't been in a bar yet.
Exactly.
You just need something.
Maybe I was 20.
And I was like, just talking about,
you'd eat some of the General Gals chicken.
You don't want it, but it's so good.
You buy a plate of the chicken.
And I think I started, it's called a false premise.
You go, how do they afford to give away the free chicken?
That's a false premise.
The chicken costs two cents.
Like that's, I didn't know anything,
but I'm arguing circular logic
to prove the stupid point. How do they afford the free chicken? Then I thought about it. This is so
stupid. You eat the chicken, then you order the plate. You don't even want it. You leave it. You
walk away. They come by, put in a couple of toothpicks, right? And like, that's the punchline
is an ellipses. Yeah. They put in a couple of toothpicks.
You're just hanging out.
I threw that one over.
You guys, I think I'll wait.
I'll leave this here.
You can finish my sandwich on that one.
That was my ellipses.
That development is not a rest.
I like the way you were kind of doing your early.
You were kind of doing.
Yeah.
My Seinfeld-eld-esque back then.
You put it, well, you had to.
See, what Seinfeld is a master of is he figured out that there's how you say it.
Right.
It's an attitude.
Like, what's the deal is an attitude.
And most people, the mistake they're making, and I'm sorry, I don't mean to turn this into a stand-up tutorial.
No.
Most new comedians, I want to pull them off stage and go, how do you feel about what you
are saying? Yeah. How do you feel? Because there's a lot of autism. There's a lot of like brilliance
and there's a lot of heavy stuff. And someone needs to go like, where in your body is that joke?
You know what I mean? I'm not saying you need to be doing this, but you need to be going.
You said that is Seinfeld. Where in your body is that joke? Where are these jokes in your body? And people like Seinfeld that figure that out,
that aren't naturally embodied and not, I wouldn't even say I can't prove this, but I have to think
he taught himself to emote on command to get a better response. That was the only motivation to learn how to talk like a human
was to get better laughs.
Because I'm sure he's even more of a weirdo.
And some comedians amplify like their personality.
Oh, yeah, of course.
So I'll give you an example that you don't care about
and you won't enjoy.
I'm just kidding.
When I was starting out, I wrote this joke where I go,
unicorn, How about
unicorn? It has no corn. Right. Then I did on my HBO special and I yell it. I go, I, it opens like
this. And first of all, the first joke of benign violation is a joke, right? The first joke is
that out of nowhere, I go unicorn, unicorn, but I'm yelling right how about unicorn that's a
joke yeah because the joke isn't just the word it's the joke is actually not to dissect the bird
but the joke is that that's what you're getting upset about right and that can be canned and
overused and fake and bad but it it went from something that's embarrassing,
never say that again,
to one of my most quoted jokes.
And it's a stupid joke.
And by the way,
my social person just posted that clip on social media.
The other risk,
the comments are full of people telling me about Latin.
And I don't know why I looked at the comments.
But I was like,
you're never too old to learn.
Yeah,
that's right.
This is also the enemy of comedy.
Some,
some new comedian would post that.
Somebody called the joke lazy.
I don't,
I really don't know why I looked at the comments.
I never do.
Someone was like,
look,
I don't mean to,
but I just got to call out this lazy joke.
Like it's uni and a eunuch.
And I was like,
you fucking,
like I'll burn down a whole,
like a reenactment village.
And that's their livelihood.
Just to spite this person.
Like I'll burn Plymouth plantation to the ground.
Do you do that digitally?
Do you get into it with people online?
Oh no,
I'll never do that.
Yeah.
I won't give the says.
You have like a fake troll account. I will say it here and they'll never hear it, but I like that. No one will ever, no, I'll never do it. Yeah, yeah. I won't give this as a... You have like a fake
troll account.
I will say it here
and they'll never hear it,
but I like that.
Yes, no one will ever hear it.
They'll never know.
No, no, I don't mean that.
Oh, that's our guarantee.
Yeah, yeah.
Cold open or no.
So let me speed forward.
I do stand up.
Two weeks later.
I get good.
I moved to Chicago.
Yeah.
Like after doing stand up
for very short, I moved to Chicago. So like six after doing standup for very short,
I moved to Chicago.
So like six,
maybe did it six times in Boston.
Moved to Chicago to do improv.
Walked by the thing.
Monday nights.
Comedy Monday.
Didn't get into anything I auditioned,
except I got an improv team,
but there wasn't enough action.
I need,
you know,
it's like late night.
I like that.
I want to turn and
burn i want a new joke new monologue new laugh let's go let's go fucking improv look i love
improv but this fucking get your 10 idiot friends together to rehearse once a week to perform once
a month i'm like you guys are not snorting the same powder I am. I've never done cocaine. I'm just saying I'm in this.
I want it.
I actually need it as an anxiety reduction.
So I was like, look, we either need to rehearse every day
and do a show four times a week
or I need to start doing standup.
I'm really glad I started doing standup
because that is all the thrill and all the pain.
It's all the risk and all the reward.
And I preferred that.
I was like, I'll eat shit and want to like cry.
You bombed so badly.
If it means maybe in three weeks, I'll kill so hard.
And also the bad ones are like pulling the bow string back.
And then the next one's amazing because you're fighting.
Like you're exactly like, it's no wonder we call it killing or dying.
It's like, it really is like a little battle.
And when you get your ass kicked, you train harder.
This is why I don't like, Swin, you're a writer.
I know you see your things on their feet, but like writers that are just sitting around
thinking about a novel, I'm like, how do you, how do you motivate that?
Yeah.
I write because if I don't write, I die.
You don't write, you get to jerk off and eat some Oreos.
Like, you win if you don't write.
I'm on a treadmill.
You're going for a walk in Madison County.
Like, I don't understand how they do it.
And yet I envy them.
I envy them as well.
I love that.
I wouldn't trade it for the world,
but if you could just kind of like
find your dad's critical voice in you
and be like, tickety-tickety, tickety-tickety.
There's like, I have shows coming up.
I have to, I have to get that joke right.
Well, and that thing you're describing,
I think you had to have that to be successful.
I don't think that you, I mean, doing, performing once a month, you're not going to get the experience that you need.
It just wasn't working for me.
You need the reps.
But wait, so after three years, you looked elsewhere and where did you end up?
Well, speaking of Seinfeld, I saw the movie Comedian.
It's a very fond memory.
I went and saw it
with Kumail. You know, Kumail
Nanjiani.
The most Italian Pakistani.
Nanjiani.
Kumail Nanjiani and I had a big bowl of pasta.
He had a unibrow and smoked parliaments
at the time. This was not...
Pre-Marvel. Yeah, pre-Marvel.
And we went to the movie theater
like where... I wouldn't even call it the movie theater. We went to the movie theater, like where,
I wouldn't even call it the movie theater.
We went to a movie theater where a comedian was playing,
but it wasn't on a lot of screens.
But we went to opening day matinee.
And we sat down,
the theater was already dark.
We watched the movie.
Of course, it changed my life.
By the time the movie ended,
I was like, I am moving to New York.
And when the lights came up,
we looked around and it was every comedian. It was all stand-up comedy. But we didn't know. We didn't And when the lights came up, we looked around and it was every comedian.
It was all stand-up comedy.
But we didn't know.
We didn't know
until the lights came up.
It looked like...
Especially the matinee.
And you all immediately
moved to New York together.
Well, you know,
it's an interesting...
It's for the bus.
To me, obviously,
because what I did
ended up working for me.
It was a really important moment.
And I wonder how many
of those guys were like, I should move to moment. And I wonder how many of those guys
were like,
I should move to New York.
I wonder how many did.
And the answer isn't a lot.
Kumail did.
Yeah.
And I did.
And look,
and a lot of brilliant ones stayed.
But what I wanted to do
was go to New York.
And I did.
And because of that movie,
almost single-handedly,
I told my wife at the time,
we're moving to New York,
like just like that.
Wow.
And not like,
like cutting a steak,
black and white.
We're moving to New York.
It wasn't like that.
Pack up the kids.
I was very sweet and very meek.
I probably just was like,
what do you think?
Next thing I know,
we're faxing.
She was a teacher,
her resume to schools
that we just found on a map.
Wow.
Having a wife where it's like,
we're moving together, that's...
Well, yeah.
I mean, this is my ex-wife
and she ended up being the impetus for crashing.
But again, to say something lovely about her,
she was very supportive and believed in me.
And when we broke up, actually,
she was like, you know, she had an affair
and she regretted the way that it happened.
But she was like, the nicest thing she said was like, I believe in you.
She's like, I think you're going to be.
Oh, that's great.
She said, I think I could cry.
I think you're going to be one of the greats.
I'm not leaving you because I think you stink.
I'm leaving you.
I'm leaving because I'm jealous.
I'm leaving.
She said, I'm not attracted to you.
She said her truth, which was, I don't, I'm not interested in being a famous comedian.
Yeah.
And that was great.
Before,
like years before I was famous.
Oh,
she got out at the right time.
That's not for me.
Yeah.
I've also joked that she also left like the year I started making good money.
I was making nothing.
Like she might have liked it a little more.
She's holding you back.
How do you like it in a mink?
Yeah.
But yeah, so no, she was supportive
and she did move to New York.
And she was working and I wasn't breaking in
and I wasn't going to start doing enough $50 spots.
I wasn't getting any $50 spots.
I was making no money.
But then Jessie Klein, you know, Jessie Klein,
she hosted a show on Wednesday night
at a place called Rafifi,
which we also rebuilt for Crashing.
It was just on East 11th, between 1st and 2nd.
And it was this alt haven.
It was like really like…
I almost always show up at things right when they're ending or falling apart.
I happened to show up at this right when it was fucking sweet.
Three Conan writers talked about it.
Todd, Levin, Dan Cronin, and Andre Dubichet.
Oh, yeah.
Andre Dubichet.
I think they all became friends and met there.
Yes.
So many wonderful people.
A.D. Miles, Eugene Merman, Bobby Tisdale.
I mean, it was incredible.
And they were all like one of a kind.
Nobody was doing the same thing as anyone else.
Did you feel like you were somewhere special when you were there?
I did.
This time in my life, I met Demetri Martin, another Conan writer,
and I made a fake newspaper.
I came home and I was so adrenalized just from meeting Demetri.
And I made a fake newspaper. I came home and I was so adrenalized just from meeting Dimitri that I made a fake newspaper in Microsoft Word and put a picture of him in it. This is truly embarrassing.
And wrote, I think my wife called me Pums. Well, let's hear the whole story first.
I know. It said, anti-Semite crashes Boston Comedy Club. No, it said, Pums meets Dimitri
Martin. And I wrote the story
of how I met him
because I left it out
for my wife to read
in the morning.
Right.
Called like the Peter,
the Peter Times
or something.
But this is how
like single focus
I was.
I know you didn't mean it,
but I looked at you
and you were kind of like,
just like a slight like,
are you sure you want
to tell this story publicly?
Indicating Joe, our engineer.
No, no, no.
Her name is Joy?
Joe.
Oh, that's more fitting.
I'm just kidding.
JK, JK, JK.
So let me, I'll try to speed it up.
But Jesse Klein had that show Wednesday.
She and Nick Kroll had a show called Welcome to Our Week.
I read about it in the Village Voice.
And the way they described it, it sounded like it was a talk show,
which is a show in the back of a bar.
But I got there and it might as well have been a talk show.
And she worked for Best Week Ever.
She was on Best Week Ever.
And I think she was a writer.
But no, I don't know what she did.
But she was an executive at Comedy Central.
And she was on think she was a writer, but no, I don't know what she did, but she was an executive at comedy central and she was on best week ever. And I, again, set the intention. I had Conan by 30, but I was like, I want to do that show. I won't tell you all the, uh, other shows I did.
Hopefully like literally like a training montage, trying to get people to notice me so I could finally meet Nick Kroll at UCB,
which I did,
and finally ask him,
can I do your show?
And finally get booked on it.
Nick's not there that night,
but Jessie is.
I do the show.
I do well.
That's important.
That's key.
It's not just networking.
It was like,
I was ready for her to see me.
Preparation needs luck.
Yeah.
I emailed her.
I don't even know how I got her email.
I must've asked her.
And I just said, I thank you so much for having me. I've always wanted to be on Best Week Ever.
It's like a goal of mine. And I've always wanted to do Premium Blend because that was a Comedy
Central show. She didn't reply. Instead, I got an email from Fred Graver, who is the executive
producer of Best Week Ever saying, Jesse Klein told me that you'd like to do Best Week Ever.
Just like that.
One of the coolest moves.
That's pretty good.
She didn't even reply.
Yeah, yeah, yeah.
She just forwarded it.
She just did it.
Right.
And he reads out, next week I'm on.
Now I'm making $400 a week doing Best Week Ever.
It was fucking incredible.
It became a regular gig.
Yeah.
It was a regular thing.
That's great.
I learned so much doing Best Week Ever that everyone here takes for granted.
It's like attitude, rephrase the question,
that say, what was it about Chuck D's response
that made you laugh?
And you'd go, the crazy thing about Chuck D's response is
like you learn those things
that when you interview like a college intern,
you go like, oh, like you don't know what you're doing.
You don't know how to talk showbiz talk don't know what you're doing. You don't
know how to talk showbiz. You don't know how to talk in soundbites. So I did that show. Then again,
I moved to LA. It's boring. I wrote a writing sample. I did Montreal. I got my agent,
Zach Drucker and Doug Luttrehan at WME. They still are my manager, blah, blah.
I wrote a modern family spec
yes
I submitted it
haven't we all
haven't we all
literally
I think it was
I have one too
the year before
they started saying
no more modern family scripts
yeah yeah
but I'm very proud
of this story too
because I had never
written the spec
I just
they sent me a sample
of a script
and I had never seen the show
and they sent me DVDs.
This is how long ago it was.
I watched a couple episodes.
I looked at the scripts.
I was like, the first scene is four pages.
There's a second scene.
Exact cold open.
The second scene is,
and that scene comes back here.
And I swear, I just, a beautiful mind did that.
I just went like, uh-huh.
Like it took a weekend. There's math involved, uh-huh. Like it took a weekend.
There's math involved.
It is.
I wrote it in a weekend.
Wow.
Because I really only did that.
Right.
And there is math involved.
Yeah.
It's like there's a musicality and there's a pattern.
Sure.
And then I was like, this guy is a corny dad.
I'm like a corny dad.
I still remember some of the jokes I had him say as Arnold Schwarzenegger.
He was playing Mr. Freeze at the time
I went
I used to see you
so I put in
parentheses
as Schwarzenegger
I used to see you
and I was like
I think I'm getting this job
and I did
oh shit
I got it
first back
first thing
on Modern Family
not on Modern Family
I got a job on a show
called Outsource
oh okay
for NBC
but that moved me to LA oh yeah now we're getting closer to Not on Water Family. I got a job on a show called Outsource. Oh, okay. For NBC.
But that moved me to LA.
Oh, yeah.
Now we're getting closer to what we're supposed to talk about.
Who cares?
Who cares?
Now I'm doing more standup and I'm 31 years old now.
So I'm a year off my cone.
Oh, wow.
Yeah. I'm a little-
The clock is ticking.
I didn't see this wrinkle coming.
I assumed.
I'm so used to- Yeah. It's like see this wrinkle coming. I assumed. I'm so used to, it's like when, you know, on my 30th birthday.
Yeah, yeah.
But you're 31 now.
Oh, my God.
31.
And you're a fucking failure.
And I had already done Fallon.
I broke my seal doing Fallon, which was okay.
I did okay on it.
But then I really was like, I'm going to get on Conan.
So I really want to, at this point I had been submitting tapes or links probably by this point
to JP Buck. Yeah. Wasn't working though. But I happened to be at the improv one night when JP
was watching someone else run their set and I was closing out. So I did like 20 minutes at the end. I did the joke, the Google joke. I had just written the joke about, believe it or not,
this was cutting edge at the time, was I have Google on my phone and it's ruining everything.
It almost sounds like a chat GPT joke because I say it's like a calculator that you can cheat
at every subject, which is what chat GPT is. But so is Google. ChatGPT is just like a very sexy Google.
It's like, let me,
not only will I tell you,
I'll write it for you.
You can also be married to me.
Yeah, exactly.
Now you can marry pornography.
I never leave the house.
It's like pornography
that also makes you a huge meal.
So he did the joke about Google.
Yes.
And JP,
and this was great.
He was like,
I want that joke to premiere on Conan.
Oh,
cool.
I've never even heard of.
We want that joke exclusively.
Yes.
And I just,
how old are you?
31.
Oh,
sorry.
And I just taped it on.
I don't know if it was John Oliver's New York standup show
or some other show,
but it wasn't going to air for a couple months.
Yeah, yeah.
But this is what you want.
You want to manufacture urgency.
So I had urgency.
Yes.
And he saw me live.
Huge synchronous.
You could just say it's a mitzvah. It was like a gift. Yeah.. Or you could just say it.
It's a mitzvah.
It was like a gift.
Now I'm going to do Conan.
I'm 31.
I do it.
Then I'm writing on the other show.
I had a breakup.
I lost 50 pounds
and I did Conan a second time.
I left my writing job.
It was on the Warner Brothers lot.
And I walked to Conan.
Oh, funny.
Literally was in the writer's room.
I was like, I'll be right back.
I got to go do a set real fast.
You know what?
I hope you took a moment to enjoy that.
Nobody gave it to me.
What?
Nobody.
They seemed to put it off.
They were so jealous.
They were kind of like, how was it?
How was it?
I'm like.
Oh, how was your little taping?
My makeup?
Yeah.
Why am I wearing makeup?
And my favorite shirt,
you know,
my favorite.
So the second time,
the first time I didn't,
the first time I'm,
I'm two 85 and I'm wearing a smock.
Oh,
wow.
Like,
uh,
like I had never won the shirt.
You really lost.
I lost 50 pounds in between my first corner and my second corner.
Bad, bad relationship. And I did a
juice cleanse, and you can tell because my skin
could cook bacon in the second one.
Radiating kale juice
the second one. And it was that
one that I didn't know that they were looking
for the
follow-up to the Conan show.
Oh, wow. And so I didn't know,
which I'm glad. Thank God.
Yeah.
Thank God.
I mean,
although you might be
really good at that stuff.
A little pressure,
I guess,
but I was already
swinging for the fences.
It's nice not to know.
But Conan was really effusive
and I remember,
I think it was Jeff Ross
was like,
he never does that.
Yeah.
Like he came up
and talked to me
for like 10 minutes
and I was like,
that was nice.
And they were like,
he doesn't normally do that.
And I was like,
really, Mr. Ross?
It's true.
Oh, really?
It is true.
You say that to all the girls.
It was very sweet.
And we bonded about being from Boston.
I was going to say,
I feel like you have a lot in common.
You're both really tall.
Irish.
Yeah.
Exactly.
Spent time in Chicago.
I went to Harvard.
I've been to Harvard.
Harvard Westlake.
But this is where I think it gets pretty interesting is that I, I,
I didn't,
I knew they were looking for somebody and I missed this naivety,
this sort of purity that I had because my manager day was like,
they're,
they're looking for someone to host a half hour talk show after Conan.
And I was like, great.
And they were like, so Conan wants to meet.
And I was just so happy that I got to meet Conan.
Like I had a meeting in his old office.
And I remember I sat down and I was nervous,
but I was also like oddly confident.
And I was like, can I sit here?
I don't want to fuck up your shit.
And I don't know why I said that. Like it was one of those like, like the first thing I sit here? I don't want to fuck up your shit. And I don't know why I said that.
Like it was one of those,
like the first thing I'm saying is I don't want to.
And he goes,
you can sit there.
You won't fuck up my shit.
And I was like,
oh, okay.
Game on.
That's when I knew we were good.
And we just talked.
I didn't know any,
I swear I was so green in show business.
I was like,
aren't we going to like talk about the show?
I didn't know.
I wonder if I had a pitch or something.
I didn't, but I was just kind of like,
and we just chatted about our families
and all that stuff.
But that was the interview.
Yeah, it was.
This is very sweet.
This is so saccharine.
But he said, I don't,
this is the last thing he said.
He goes, I don't know what it is about you,
but when I'm with you,
my funny tuning fork vibrates.
It's a weird phrasing, I suppose.
So I had my little Warner Brothers parking pass
and I framed it and I drew a tuning fork on it.
It's still in my office,
but I remember being like, that's what I got from that.
I got a parking pass and a tuning fork.
Next thing I know, we go back to the TBS, which
probably means six months.
But next thing I know, we get
another call. You're going to meet with Jeff
Ross, not the roastmaster,
Conan O'Brien
at his office. And this is
how it went down. I'm sitting
in Jeff's office,
which used to be much bigger.
Yikes.
And, uh,
You weren't supposed to go up there.
And I'm sitting next to Conan
and he's wearing his Indiana Jones
light brown leather,
which I was like,
it was so weird to see
Conan in the wild.
I like,
that was so kind of,
again, I still get excited when I see Conan,
don't get me wrong,
but it was really like,
he wears leather?
Like what?
He doesn't seem like a leather guy.
Like I didn't know he's leather.
This deal is off.
I walk.
I draw the line.
And in the meeting he says,
well, we're going to go to TBS,
tell them we want to do a talk show and we're
going to tell him that we found the host. And I swear to you, I thought, who is it? I did. I went,
who is it? I didn't say it. I knew well enough to shut up. But I was like, and it slowly dawned on
me that he meant me. And it was like And it was like fireworks went off in my body.
But I was just sitting there like.
And he knew how to deliver that news to you too.
Do you know what I mean?
Like kind of.
He did it.
It's still that way.
Because he's one of the few people who's been in those shoes.
I never thought about it, of getting that kind of news.
He did say, look, I would say this if he was in the room.
He's like, we're going to tell TBS you have to be on the air for a year.
Oh, wow.
We're going to tell them you pick us up.
You have to be on for a year.
Yeah.
It didn't happen.
But that's not his fault.
You did do a couple seasons, though, didn't you?
Here's what happened.
It's a little more spicy than that.
And then I died.
We shot the pilot on the Conan, yeah.
On the Conan set, which was a thrill.
And the guests were Nick Offerman for one,
Bill Burr for one.
That's the one we used and TJ Miller for another.
So these-
That's good.
How much time went into getting ready to do that pilot?
What was great was for the monologue,
I did my closer,
which was one of my best closers of all time.
And it just so happened to be clean.
Okay.
And I just did the story.
Great.
And it was like some fake way in.
So you had that done.
I was like, I'm doing this new thing.
I'm not always the most comfortable guy.
And then I tell a story.
Oh, great.
But we knew that was going to murder.
And it did.
And we did it again when we shot the proper pilot.
And then we were most worried about the guests.
And the moment that it's hindsight being like,
I knew we were going to get picked up.
I knew I did a good job.
Because Bill Burr was the guest.
And this is sort of before Bill became like the most legendary Conan guest of all time.
Right.
Yeah.
Who always comes on in 20 Slays.
12?
I'm bad with time, but that sounds right.
Okay.
And he was doing a bit.
And it was perfect because it was just getting a little tense.
Just a little tense.
A little Burr tense.
You know, you get a little Burr on your sock.
Yeah, yeah. You get a little Burr on your sock. You went through the meadows, you got a
burr on you. And he's, he's talking about Hitler, your favorite. And he's going, he's been going for
a while and I'm, I'm the host. I'm supposed to shine. He's doing great. He's doing what he's
supposed to do, but I'm kind of going like, what, how do I score and help him score? And he's going to Hitler, giving these speeches. He goes, how did he, how did he convince all
those people? I've seen the speeches. And he goes, well, what was he saying? What was he,
I mean, what is he saying up there? And I go, and the joke came to me, sorry to, you know,
my own war story, but I lean in and I go, probably a lot of hear me outs.
And the crowd goes wild.
And I had gotten the card to wrap.
Oh my God.
And I closed it.
Yeah.
And I go, when we come back a little bit more with Bill,
just like my dream, I'm throwing a commercial.
And as everyone's clapping, Bill goes,
that's very funny.
And I was like, and this is the guy
that I opened.
That's right.
In Chicago.
And he,
and it's part of why he did it.
He was like,
oh,
that guy that I opened for.
I literally opened for him
in Peoria,
which is where Richard Pryor's from.
Oh, yeah.
Where the birthplace
of the expression,
will it play in Peoria?
Right.
Meaning,
will regular people get it?
And I ate shit
most of the time,
but Bill liked me and it all
came back. What is this?
The movie Big Fish? Like, what the fuck
is happening in this tale?
But it's so charmed
and it's such a pleasure to remember. So we shot
it. Here's where it gets kind of interesting. TBS
went ahead and told us they had no intention
of picking it up. Here's why
I know that. And then I die.
I know because the deal
that we wrote out,
if this goes to series,
here's what Pete gets,
here's what the writers get,
money-wise, budget-wise.
They were like,
look, we want to pick it up.
We can't honor that contract.
That was,
and Conan knows this,
that was to placate Conan. He's our
guy. He wanted to do this. We said, yes. Oh, wow. We gave you like a fake contract. Like,
like, uh, yeah, we'll give you, uh, it wasn't a ton of money, but it was like, I don't know.
I don't even remember what I made for that show, but it wasn't, it wasn't a ton of money and I'm
not complaining, but they, the contract was more generous and they're like, we want to do it.
We didn't expect it to be this good. So good news, bad news. We want to do it,
but we want to renegotiate this because we can't afford to do this.
That's insane.
Isn't that wild? Yeah. This is like old showbiz.
That's literally like a bait and switch.
I know.
Yeah.
Good news, bad news.
Good news, bad news.
Yeah.
And again, it wasn't necessarily framed like that.
Like I'm saying it very directly.
Right.
Yeah, yeah.
That's my recollection of how that happened.
Nobody was like,
smoke a beer for a while.
Man, I called Bob.
Man, I called Bob.
Nobody was like that.
They were just like,
my manager was like,
they want to make the show.
That's all I heard.
There's just one sticking point.
I was so thrilled.
No, I was on the toilet
when they got canceled.
Anyway,
I was doing Elvis
when it got canceled.
But the way that we
justified the budget
or whatever,
because it was a very low budget,
was we would shoot
six episodes a week.
And it was non-topical.
So there we are
like shooting in the summer
and I'm like,
Valentine's Day is around the corner.
Like literally.
That's a classic thing.
And was that to air
every night or to air once a week?
Four times a week.
Just like you guys.
Monday, Tuesday, Wednesday, Thursday.
And we would bank episodes.
But here's,
it never would have worked.
Not,
I consider the show a great success.
I actually, believe it or not,
have a lot of fans.
And because of,
thank you,
that means a lot from you.
And from Instagram and TikTok,
for real.
But Instagram and TikTok,
no, but my compliment,
I'm sincere,
is giving it this whole second life.
And YouTube gave it this whole second life.
Is TBS in this weird pre,
for once the artists benefited from like a,
we didn't know what to do with streaming stuff.
They let us have it on my YouTube.
Oh, that's great.
That was like in the deal.
Yeah.
You can host it on your YouTube.
This is before anyone knew what YouTube was
so before you know it
they could monetize it
yeah
there's like
we should have monetized it
by the way
yeah yeah
like that would have been
incredible
but I can't
because I didn't pay for it
but they could have
that was kind of dumb
sorry
I'm just in my brain
counting the money
I know
I'm sorry
I went to a taping once
and you had on a
new material.
Was it new material Seinfeld?
That made me laugh
really hard.
Who did that voice?
Joe DeRosa.
Okay.
My dear friend.
Oh, yeah, yeah.
New material Seinfeld
was something I used to do
just to make people laugh.
It is very funny.
I was like,
well, what's a cup?
Glass bowl,
but it's tall,
tall bowl.
Tall bowl.
Hollywood bowl. Why is it a bowl? It's not a bowl. It's a shell. Shell gasoline. glass ball but it's tall tall ball tall ball Hollywood ball
why is it a ball
it's not a ball
it's a shell
shell gasoline
it's not gas
it's a shell
what's a dinosaur
fossil
fossil jeans
jeans
you put on jeans
diesel
Vin Diesel
does he wear diesel jeans
and like you just work
and do a thing
and then you go
is that anything
that's my favorite
you have a pad and a pen.
That's it.
This is how I know.
Do you feel he did it justice?
He did do it justice.
He was great.
What were you going to say in Tripped?
I was going to compliment and say a true comedian, you, knows that the joke is, is that anything?
Yeah, yeah.
Like someone watching is like, I like the part.
No, the audience, that would kill when he goes,
is that anything?
Is that anything?
That's the punchline.
But Nate Fernald,
one of our writers,
I remember he wrote this joke.
It was so Seinfeld.
It was so good.
It's really a testament
to how clear Seinfeld's voice is.
I'm not saying that
just to kiss his ass,
but I'm kissing his ass a little bit.
But he's like,
he's like,
macaroni. They always have the clear, he was like, uh, macaroni.
They always have the,
uh,
the clear window.
Then you can see the macaroni in the box.
Yeah.
He goes,
meanwhile,
cereal's over here in the dark.
Why is macaroni getting rid of you?
I was like,
that is a great,
that's a great joke.
It's ready to go.
That is a great joke.
You could give it to Seinfeld.
It's so ready to go. So cut to me You couldn't give it to Seinfeld I was like It's so ready to go Yeah
So cut to me
This is actually kind of a synchronicity
Because I went to the Palm restaurant
For the first time yesterday
First time since this happened
The first time I went to the Palm restaurant
Which is like a famous
Yeah
Hollywood restaurant
Like very sceny
The faces of famous people
On the wall
Yeah, yeah
And they bring you a prime rib and a martini
at 11am
on a Sunday
so I went to the Palm
and I was telling this story
that I was like
the first time
I was there
was Jerry
Judd Apatow
my dear friend
and I mean that
like we're actually
very close
I love him very much
and we talk
all the time
and I don't know
why I'm getting sweaty
about that
I just mean like
he's just a like he's just a comic.
He's just like a new balance.
He wears this shirt every day.
I'm dressed like him.
Regular guy.
And I love that we can be pals.
And he invited me to this thing that Jessica Seinfeld,
so Jerry's wife, was having a fundraiser.
And I was laughing with Val,
looking back that I was like,
that had to be like a five,
maybe $10,000 seat.
And Judd, like classic rich guy thing,
didn't have anyone to go with me.
I'm sure Conan's been like,
Sweeney, do you want to come to Mick Jagger?
He's never asked.
No, Mick Jagger's having an Easter egg hunt.
Yeah, yeah.
To raise money.
Gotta show my face.
Anyway, but I don't really eat meat.
Even though I ate steak yesterday,
I still don't consider myself a red meat eater.
So they're bringing out these steaks,
these incredible steaks.
Jason Bateman is there.
Judd is there.
And then I'm like, I don't even,
they bring me the saddest mushroom
I've ever seen in my life.
It was a $10,000 portobello.
And I was just thinking
about Judd being like,
uh-huh,
I paid for this.
I invited the wrong motherfucker.
So that was to redeem that.
Here's why I bring it up.
Okay.
I'm counting it as a synchronicity.
Jerry Seinfeld is there,
of course.
This is the man
who changed my life.
I saw his movie.
Right.
Yeah.
And I moved to New York
and everything changed.
He comes up to me.
I have no stories like this.
I'm in a dumb blazer like a Sunday school student.
He looks amazing.
He walks up to me and he goes,
What's with the mushroom?
He goes, what's with the mushroom?
I'm sorry.
Why is it a mushroom cap?
It's not a hat.
It's like, it's a shade.
It's not graduating.
It's not graduating?
Move the tassel?
Move the fungi? I'm a fungi. She it's a shade. It's not graduating? It's not graduating. Move the tassel. Move the fungi.
I'm a fungi.
Mitochondria.
Psilocybin.
He says, but I also blow it in this story, I think.
He goes, I, he goes, I just want to say.
He doesn't do it.
He's a regular boy.
I just want to say.
You can't help it. That's better. He's doing it doesn't do it he's a regular boy I just want to sign you can't help it that's better
he's doing it as a puppet
that's him regular
he goes
I saw that new material
sign
oh god
wow
and I loved it
oh that's
and I
this is where I think
I blew it
but it was honest
I couldn't stop myself
if I tried
to quote your friend
Mick Jagger from the Easter egg
thank you
wild horses
couldn't have stopped this
I went like this.
I went,
and I,
and I immediately cut to him later.
Pete just did a mind blowing mind blow with the two hands,
like pans,
labyrinth and my eye pop.
And I just,
you know,
he,
he rolled with it,
but I was like,
that's exactly like an episode of Seinfeld
where he cuts in a diner.
He did the mind blow.
You don't do the mind blow.
A legend of comedy comes to your chair,
you don't do mind blow.
Because it took up too much space.
Yeah.
Well, if your hand hits him in the eyes on its way out.
My wingspan is just too great.
It's like the conversation.
I think I did manage to squeak out,
thank you for making me do it.
I'm sure you did.
Yeah.
I think you're over.
I think you're being,
that seems like a totally normal.
I appreciate it.
Nice response.
I mean, what are the chances?
You're narrating the moment in the moment,
which is what's funny about it.
How could he have seen it?
Yeah.
How could he have seen it?
Somebody probably sent him the YouTube clip, to be honest.
But like, it was a highlight for sure.
That's so cool.
So we did the show and we got two seasons
and there was like six months in between the seasons.
But here's the, it even worked out,
getting canceled when we did worked out
because the way we were doing it was evergreen.
It was never supposed to be that way.
So we're not interviewing celebrities when we're,
I'm talking to Adam Scott when he has nothing to say,
which was so hard.
It was actually kind of pre podcast though.
It was like,
just what's up.
Tell me about your family.
That's true.
Yeah.
And then we did all of these sketches and Batman sketches and Doctor sketches.
And we just had access to like Conan's toy box and your art department and your talent booker.
I was wondering, was it sort of...
It was incredible.
It was produced by some of the same people, but then you had your own writers.
It was all the same people.
We had our own writers, but we felt
incredibly resourced.
But we had Billy Balatino
directed most of them.
A lot of the same
camera people,
Peter,
I'm trying to remember
the camera guys,
but Peter's one of them.
Same cue card guy.
Right.
And it was just like,
looking back,
boy, I'm going to be
in a good mood
the rest of the week
because I'm just like,
I really was handed the keys and Conan really was like, do whatever you want. Here's
how, and this is also what's great about it. That's nice to have someone like that behind you
too. And he was behind us and we felt that and TBS and I'm grateful to TBS. It's all different.
Everybody at TBS isn't the same people. Oh yeah yeah, yeah. But here's how not watching us they were.
In the pilot, the first episode,
I said, fuck, and they didn't believe me.
Oh, wow.
That's how unwatched we were.
And when we, there was like a real,
almost like Lampoon-y revelation
where we realized there was like a moment of sadness
where we're like, no one's watching.
And then we were like, like a movie,
it'd be like pushing in, no one's watching.
And we started doing just like, you know,
I flatter myself putting us up
with like the Ben Stiller show and stuff,
but we had our own smaller version of like,
we can do whatever we want. We swore so much. We were doing
like, it was very dirty at times. I'm drawing dicks and stuff. It's not getting blurred. Just
very adolescent. And it was this time in my life, I was single. And my brother actually loves the
monologues because he's like, it's a, it's a snapshot of a single man figuring out how to be
alone in the world. Not alone, bad alone. Yeah. But like we did a monologue like called have a
morning and it was the most earnest, like, don't just set your alarm before you have to go get up
early, read the paper, make some coffee. But it was like the most earnest. Like I had
just figured that out. You're just becoming human.
Yes. And I would think of
the monologues driving in. I lived in
Los Feliz and I'd drive through
Griffith Park and I'd have all
of these monologues. We'd write a monologue.
I saw a guy, yes, I saw a guy
on a motorcycle, but like
one of those fat motorcycles with like
compartments on the back. We just did a whole,
the three wheelers.
Saddle bags.
A whole monologue about how
not all motorcycles are cool.
Yeah.
And would put it on its feet
that day.
That's amazing.
And you get into that like
white hot mania.
It's not bad mania.
Like Charlie Sheen,
I'm not trying to make
fundamental illness.
I'm just saying,
wasn't bad.
It was like,
it was like drinking from a waterfall.
You're like,
think it,
do it.
And,
and I'm really,
really proud of it.
And,
and,
and Jamie Lee and Nate and Joe DeRosa was one of the writers as well.
Adam,
I'm forgetting.
I'm always Nate from,
I'm going to forget some of them,
but really incredible people.
And of course,
Oren Brimmer,
who directed all the sketches and wrote.
Oh, great.
And we still work together.
And Matt McCarthy.
Oh, I love Matt.
Who was in everything.
He's such a great performer.
Our lives have been so long that Matt and I and Oren are working together again.
I'm not promoting anything.
We just started going like, you know, what are we doing? We have different
projects. All of us have different projects from time to time, but we're like, let's just go back
to the basics. Let's scrap together some money, get a space. This would be a great space, you
fucking assholes. I think it might be available after this. Actually, I'm a hundred percent
getting when I call you assholes, I'm like, maybe available after this. Actually, I'm 100% getting
when I call you assholes,
I'm like,
maybe you guys could
let us use this room
because
it's those clicks away.
We shot,
we're about to release
Batman Fires the Justice League,
which is me as Batman
just letting everyone go.
Yeah.
We did that with X-Men
for the Pete Holmes show.
Yeah.
And now, you guys know, it's like when
your career is long enough to have these phases where you're not together and you kind of miss
each other and it's sad. And then you get back together. You know what was the best was when we
were just making stuff. Yeah. You're just doing it for its own sake. And then it becomes like,
because you can, I say this in a great way, not a slimy
way. You can monetize it. You can hopefully get enough views that these guys can get work out of
it now. And now everyone's like benefiting from a legacy that we created together. And then it'll,
it'll branch out into this. So if, if you see those, please watch them. Yeah. That's great.
I love that you're going to be sketch comedy it's really yeah it's exciting
I will say
this is the last little
so this is a sweet nug
oh please yes
I'll tell you
two sweet nugs to close
bring it home
two nugs
we did one of the most popular videos
in the hardest bit
that killed the hardest
we ever did on the Pete Holmes show
was called Romano Duets
I did a video called Romano Sings
we just shot it in Oren Brimmer's apartment in New York.
And this is before you even said it went viral.
It was popular.
And it got back to us that Ray Romano had seen it
and we were unbelievably thrilled.
Cut to years later, I'm doing a talk show.
A lot of the things we did on the Pete Holmes show
were things that I had already done very low budget.
So we did the X-Men series where someone's firing Vega because you can't.
Oh, the Street Fighter series.
He's firing Vega because you can't bring a claw into a street fight.
I mean, the joke is right there.
But I didn't have any friends or cameras.
So I just shot it in photo.
I made Photoshop stills.
Oh my God.
And this is kind of before that was a thing,
like lo-fi, not animated,
just cutting back and forth A and B.
And I had Premiere.
I stole Adobe Premiere off a Torrent site.
And I just made it
and I just voice acted it in my little room.
And of course, I love this story.
Then we later shot it with Thomas
Middleditch and it's one of our most popular videos. And we did Romano sings with a literally
a felt green screen and it did well. And then we got to reshoot it for the Pete Holmes show.
And now it's beautiful and it's looks a lot better. Then someone's like, do you think we
could get Ray Romano to do it? And we'd do Romano duets? So we did do it and you can watch it.
And I stand by it.
It's very funny.
But the best part was we're on the lot, stage nine, I believe.
And I'm standing in the dark and, you know, there's a proper green screen.
And I'm just kind of doing my part before Ray gets there.
So I'm at the mic and I'm like, hip hop hooray.
Oh, hey, you know, doing that. And the door.
It's a little Kermit-y.
Oh, it's very Kermit-y. Yeah. We used to do it. It's like Ray Romano's like, yeah.
Then like Kermit is like, hey, hey, hey.
Oh yeah.
And Ross Perot is, ah, and Aziz is, wow. It's like, they're all sort of like.
They're all on the same spectrum.
They're all a blend.
So I'm doing it and I'm really,
I'm wearing, my hair is dyed black and I'm wearing his style of shirt.
But it's like kind of like making fun of him a little bit.
Having fun with him.
Yes.
But I hear a door open and it's dark
and I just hear in the distance, he goes,
my poor wife.
If that's what I sound like.
And he walked in and he did it.
Oh,
that's great.
One of my fans.
Then we played it on the stage and it murdered.
Yeah.
Like standup level,
like rolling.
I was like,
this is the greatest thing we've ever done.
I missed a good one with Jeff Ross.
When Conan auditioned on 30 Rock, he was filming like a test pilot and he was very green and he
didn't know what he was doing. And I told Conan how much it meant to me and Jeff that in the,
between acts one and like two and three, like before, after the desk bit, before the guest,
Jeff handed very nervous
green Conan
a note that said,
you're killing.
And that's in
The War for Late Night.
And I just mentioned offhand
how much that meant to me.
And before Bill Burr,
before I interviewed him,
he handed me a note
that said, you're killing.
Oh, that is nice.
The other framed thing I have.
Oh.
That's in my office.
And I,
it's a treasure.
So,
then the show gets canceled and
this'll just lead into the next chapter, but, uh, we don't have to go into it. I mean, this'll be
okay to close. I'm on the toilet. They call me Elvis style and they're like, the show is not
getting picked up. You know, when all your reps are on the call, it's either bad news or good
news. And this was, this was bad news. But we had done 80 shows, 80 shows.
And we had literally done as many shows as we could have done before it started getting bad.
Like for real.
I'm a good spin doctor, but I was like-
You got out on top.
How many St. Patrick's Day monologues can you do?
Were you just-
You've gone through-
29.
Yeah.
You've gone through a full year of holidays.
Hilarious.
But at least you also had what was going on.
Yeah, yeah.
29.
You've been waiting for someone to ask that question.
So we got out when the getting was good.
And then just to tell you,
again, out of gratitude,
what it did was Judd was a fan of the show.
He did a sketch on the show.
On the show that this aired, the joke was that I would pitch.
Everybody has this pitch for Judd, by the way.
If you're doing a sketch with Judd, come up with another idea.
But we didn't know that, which is I'll pitch you bad movies.
It's the stupidest idea.
You know, we had a lot to learn.
But I remember pitching him a movie called Beargician and Froggician.
And but then Jed's a great improviser and he goes off script and he like completely deadpan
is like, what's your real idea?
Like, what's your real idea?
And I'm like, that's actually terrifying.
Like now thinking about it, who cares?
At that moment, I was like, Jesus.
Like, it's almost like, it's almost not fair.
Yeah.
You know what I mean?
It's like Bono is like, but if you did open for me, what would you play?
Yeah.
You know, and you're like, gotta go.
So in that moment, I go, well,
uh, I was married when I was 22.
My wife left me when I was 28.
I was very religious and I got very sad,
but I ended up falling really hard into the standup comedy scene.
That was not pre-planned.
But on the top of your head,
that was your pitch.
Yeah.
I was just like my life.
And he goes,
that just sounds really sad.
And that was the joke. It made the sketch was that he was like, your life sounds better. That would just make
people want to kill themselves. I was like, okay. So the show's canceled. I'm on the toilet.
And I love sharing the story just because like, hopefully it can give people hope. So it's this
low moment and you know, what are you going to do? Like, is that it? And I called Oren and we were in that rhythm.
We were making stuff.
We were doing stuff.
Yeah, you had momentum.
And we believed in ourselves.
There's nothing like when you, I don't know much about sports,
but when a basketball player is in the pocket or on fire
and they're just hitting shots, get the ball to him because he's in.
It's unconscious. Yeah, you're in the flow. Right. And that's how I felt. So I was like,
okay, I'm lean. I don't mean physically. I just mean like I'm ready to go. Let's not mope while
the show is still airing because it was going to air for like six more weeks after it was canceled.
You had that many in the can. Maybe it was, I'm making that up.
It might have been three weeks at least.
That's amazing.
That's a real hit of steam.
Yeah, exactly.
Totally.
I was like, let's go to Comedy Central
and we'll pitch them a sketch show
because our favorite part of the Pete Holmes show
was the sketch show.
So we go and Kent Alterman was the head
of Comedy Central at the time.
I like, he's a good guy.
He's great.
I love Kent very much. And like, he's a good guy. He's great. I love Kent very much.
And we were not in a Hollywood way.
Like I just for a second
caught myself sounding like a phony.
Oh yeah, love him, love him.
Yeah.
We've had drinks and like opened up.
It's been beautiful.
But we had this meeting
and it's a warm room
and they knew the show
and they were fans.
And before the pitch,
they said, Kent said, well well one thing's for sure we don't want another fucking sketch oh my god and me and oran are sitting there like like wallflowers
we're like oh god yeah oh god no neither do we i wish we had the i I bet we did like, oh, are you kidding me?
Schumer, Key and Peele, get out of here.
So we just, we literally pivoted and acted like we were just there to touch base.
Yeah, yeah. Okay.
Yeah.
But the frustration of that, again, I want action.
I want to go.
It's like the standup improv thing.
I'm like, I've had a taste.
I don't mean of fame and I don't mean of money.
Certainly not.
I just mean like I've been making comedy.
This is what I wanted to do since I was fucking six years old with the big dick jokes.
Got to stay in the forbidden city like George.
George Costanza.
So I'm in my car outside of Comedy Central
and in this moment of frustration,
like kind of feeling down,
like, well, that was the plan.
I asked that question,
which I feel like people need to,
this is the swelling YouTube violins,
you know, when people appropriate your content
and get millions of views and put ads on it.
Pete Holmes blows me away with an
inspirational speech. But I had the courage and the vulnerability to go, no, really, if you could
do anything, what would you do? And that's a vulnerable thing because if you really admit
that to yourself and it doesn't happen, you're the guy in the wet bathing suit at the buffet, right? And I said, I would do a show like Girls with Judd Apatow on HBO.
And I was like, okay, what would that show be?
And I was like, well, it would be about me being married.
Okay, that's, I'm slowly, believe it or not, at this time in my life, I'm almost 33.
I'm finally putting together what's unique about me.
Thanks to the talk show. Like, oh, I didn't know that was weird. Religious. I did. Married so early. Divorced.
And then I was like, and then I thought of the engine of the show, which was, oh, every episode,
I'll stay on a different comedian's couch. And I was like, oh, and I'll call it crashing. So I literally, that was on a Tuesday, booked a flight.
I asked Judd's office if I could pitch him something.
Because he had been on the show, he said yes, but he was shooting train wreck.
So I flew on that Wednesday to fly to New York,
spent the night Thursday morning at like 6 a.m. on a couch.
That was the pilot.
We shot it on an iPhone.
Pitched him the show and it just went from there. Thursday morning at like 6 a.m. on a couch. That was the pilot. We shot it on an iPhone.
Pitched in the show.
And it just went from there.
So the Pete Holmes show even bled into that.
So how long after that Comedy Central non-meeting? That was Tuesday.
I pitched to Judd that Thursday or Friday.
Wow.
You really were amazing. I have a Wow. I literally have like a Delta.
I have a Delta.
I wish I still had it.
Like cocktail napkin where I wrote out the show.
Wow.
Oh my God.
And it fucking, and this is key
because that could just be mania or momentum.
He was like, write the pilot.
And just like my modern family,
I wrote it in two days, turned it in.
And I've seen Jed work with a lot of people
and the number one thing that happens,
and I can have this too,
sometimes the whole table is set.
Yeah.
The meal is there,
the fork is there,
and you can't eat it.
I see this happen.
Like it's imposter syndrome,
it's fear.
Yeah.
Self-sabotage.
Fear of success,
self-sabotage,
unworthiness, all this sort of stuff. But because the Pete
Holmes show had me at like an Olympic, like my body fat was zero. He said, write it. I wrote it.
Yeah. Because you're doing six shows a week. But it was, this is helping me realize again,
how grateful I am to the Pete Holmes show and to Conan and to Jeff and to everybody and to TBS,
even though I shit on them.
It's okay.
All those people.
You pled ignorance about TBS.
That's right.
Which is different.
That's true.
It was like running with weights
or like running underwater.
Yes, absolutely.
And then he said, write it.
And I wrote it.
And he said, rewrite it.
And I rewrote it.
And he said, rewrite it.
And I rewrote it.
I was like, and Judd, like minds like that, minds like Conan and
Judd, they want that. That's their dream too, is to find someone who's like young and hungry and
ready to go. And this is stupid to be like, and the rest is history. And that, it was like swinging
from a vine to another vine. And it was incredible. No, that's right. It's so cool. And that, it was like swinging from a vine to another vine.
And it was incredible.
No, that's right.
It's so cool to look back at it in that way
and have those things that at the time
probably just felt to you like,
this is, I'm partly running on just instinct
and following these leads
and kind of like trusting my gut on things.
But then you look back and you're like,
no, this path makes sense when you look at it in this way.
Yeah, yeah, yeah.
I have fantasized about winning an award later in my career.
Okay. So I was wondering what your next manifestation was going to be.
Yeah, yeah. Here it is. And by what birthday?
I say one behind me. Yeah, yeah.
40. So there are these gratitudes, but here's the one that I can't wait for. And it's not for
the award. It's for the speech.
In the speech, I've laid awake many nights
being like, how fucking great.
Let's say I'm on some show.
I win an award and I go up and I accept it.
And I go, I'd like to thank Conan, Jeff Ross,
and JP Buck, and Nick Bernstein.
And thank, it's absurd.
It's not, it's like somebody with a cigar go,
it's not done.
You know what I mean?
But like, and then take that to Judd
and Judah Miller and Oren Brimmer and Matt McCarthy
and then lead up to the show that I'm on.
But like, I'd love specifically,
even more than crashing,
to give that,
that first break,
the thanks.
And so that's been my fantasy.
Not to thumb my nose at Hollywood
or the future,
you know,
hypothetical show,
but just to like,
how long did it take me to say,
I want to thank Conan O'Brien,
Jeff Ross,
and J.P. Buck
for giving me my first break
on the P-Dome show.
Because it clearly was this incredible push down the mountain.
But that is a better look.
I mean, every award is really almost more of a lifetime.
I mean, you know, occasionally an actor will win something at 22 or something,
but usually this is a culmination.
Which also reminds me, this isn't to...
I guess there is a certain defensiveness
where you want to be like, it wasn't just,
I didn't win in like a lottery.
Yeah.
It was a show where you do monologues,
interviews, and sketches.
I was doing standup monologues.
I was doing podcasting early on.
So I was doing interviews.
That's how they knew I could interview.
Yeah.
And I was doing sketches. That's how they knew I could interview. Yeah. And I was doing sketches.
That's how they knew.
Right.
But that's, again,
swell the violins
and the YouTube misappropriated clip.
That,
it was like I was doing the Pete Holmes show
and then they gave me the Pete Holmes show.
Yes, exactly.
It was the easiest yes in the world.
Yeah.
So, you know,
it was my version of
dress for the job you want.
We were doing these sketches in,
if we could find a corner, we would go, that kind of looks like a doctor's office.
And we'd film 10 sketches.
And you do a podcast way before you were like, and this will pay my mortgage.
You were like, this will be something I upload.
Like, I think people will listen to it.
So there was a purity to that too.
I just don't want anyone hearing this and being like,
oh, all I need to do is be tapped.
I get the job and then I start doing the work.
No, you do the work and then you get the job.
And there is obviously luck and timing
and all of these things that are completely out of my control.
And, you know, they say like enlightenment is a gift.
This is a weird parable to say,
but somebody goes to a Zen master and they're like,
if enlightenment is grace,
meaning it happens to you like an accident,
you know, like it's just given to you by the universe.
Why do we do all this practice?
And the master says to be as accident prone as possible.
And that's how I feel.
It's like making it, making it, getting tapped,
getting this,
getting that,
is grace,
is an accident,
is luck,
or whatever you want to say.
You can put yourself,
stand in the hallway
where people keep getting lucky
or whatever,
you know,
it might help.
You should,
I'm fascinated by
all the bits you did before
that you got to redo with a bigger budget on the Pete Holmes show.
Might be fun to do like a little behind the scenes.
Side by side.
And show the original and then how you did it.
That's cool.
Yeah, and you talking about it.
That's a fun idea.
I think that would be cool to watch.
Yeah, with a little director's commentary.
Yeah, yeah, yeah.
I think we could do that.
Yeah, yeah, yeah.
That's a great idea. But anyway, I think that would be fun. I'm going to write a little director's commentary. Yeah, yeah, yeah. Yeah, I think we could do that. Yeah, yeah, yeah. That's a great idea.
But anyway,
I think that'd be fun.
I'm going to write it down.
Executive producer Mike Sweeney.
I'd like to see it.
Yeah.
And I'd like you to thank me
when you win that award.
And for the guy
who had me do
the behind the scenes videos.
Well, this is great.
Yeah, this is so great.
Thank you, Pete, so much.
Thank you, Pete.
Here's the longest
Inside Conan.
It is.
In our family, we call it shorty.
Fucking circle.
Thank you to Pete Holmes.
Yeah.
And guess what?
Pete has his own podcast.
What?
I knew you thought he was a little too comfortable in front of a microphone.
He did seem like he didn't seem to be in a rush to leave.
Very comfortable.
And his podcast is called You Made It Weird.
Right.
It's a great podcast.
It is.
Be sure to check it out.
And we have a listener question.
Ooh.
I don't know if Pete does that.
I don't know if he's got the guts.
He doesn't have time. But we take our listeners head on. We have plenty of time. We have time to fill.
Here's our question. It's from someone named Tara. Hi, Jesse and Mike. I was just listening to your
recent podcast intro where Jesse stated that since she was born in Panama, the country, she cannot be president
of the United States. This is actually false. If you are born to two parents with US citizenship,
you are considered a natural born US citizen and are in fact eligible to run for president.
And she quotes the law. Wow.
Yeah, so there you go.
And so this,
I don't think really is a question.
It's more of a correction, I guess.
It's a correction.
Which I appreciate.
Maybe we'll segue into
just have corrections every week.
That would really fill up.
That would fill a lot of time.
So, Jesse, you can do it.
Jesse for president.
Yes. Oh, boy. I would love it. Jesse for president. Yes. Oh, boy.
I would love it if
you were president of our country.
Oh, God.
I would hate to do it. I would
absolutely hate it. My favorite
part of it would be you still
carving out time to co-host
Inside Conan,
an important Hollywood podcast.
You got to do it. Sorry, under contract. You gotta do it.
Sorry, security counsel.
I'm actually disappointed because my whole life
I've been using this excuse
of not being allowed to run for president.
Right.
And I thought, okay, I'm off the hook.
Yeah, no, yeah.
She's absolutely right.
You can run.
Too bad you're not old enough.
You have to be 35.
Do I know how to butter up the ladies?
I still got it. I would never want to run for president. And we've talked about this before,
that I feel like running for president should disqualify you from being president.
Oh, yes, yes, yes, yes. Even just the desire to be president
tells me you have no business being president. You have a serious mental defect.
Yeah.
Anyone, yes, you'd really truly want to lead.
There should be like a bucket of names of people who want to be president.
And then you immediately just put a red flag by all those people's names.
Burn.
Never allowed.
Pour gasoline in the bucket and set it on fire.
And then the rest of the people, there's a lottery and each of those people have to serve
for one year.
They have to do it.
Yeah.
I think that's a great plan.
You can winnow down that group, like get people who everyone actually is like, wow, they're
really.
Yeah.
Yeah.
They're good at their job.
And then.
And then force them.
Make them do it.
And they don't have to run.
You just get selected. Right. And I think- And then force them. Make them do it. And they don't have to run. You just get selected.
Right.
And I think you could, how do you make them do it?
You could kidnap their family and hold them at gunpoint for a year.
Yeah.
And then they have to do it.
Right.
Or threaten them, say that your family has to be president if you don't do it.
Your brother, your brother who you hate or your sister.
Well, how do we get this into law?
I don't know.
I think I have to run for president.
There you go.
Just,
we've come full circle on this one.
Well, thank you, Tara.
Well, thanks for your correction, Tara.
Yeah, Tara.
I'm not too big to admit when I'm wrong.
Yeah.
If anyone else has a correction for us, please.
Or a question.
Or a question.
We'd love to hear from you.
You can give us a call and leave a voicemail at 323-209-1079 or email us at insidecodempod at gmail.com.
Yes.
Yes.
Please do that.
And if you like the show, even with all its errors and grave mistakes, you can support
us by rating Inside Conan, an important Hollywood podcast on iTunes and leaving us a review.
You know what?
I'm not wrong about.
What's that, Jessie?
Loving you.
Oh, my God.
It's the right thing to do. Inside Conan, an important Hollywood podcast
is hosted by Mike Sweeney and me, Jesse Gaskell. Our producer is Lisa Burr. Team Coco's executive
producers are Adam Sachs, Jeff Ross, and Nick Liao. Engineered and mixed by Joanna Samuel.
Our talent bookers are Gina Batista and Paula Davis
with assistance from Maddie Ogden.
Thanks to Jimmy Vivino for our theme music and interstitials.
You can rate and review the show on Apple Podcasts.
And of course, please subscribe and tell a friend
to listen to Inside Conan or an enemy
on Apple Podcasts, Stitcher, Google Podcasts,
or whatever platform you like best.
I'm not going to tell you what to do.
Put on your hat, it's the Conan Show.
Try on some spats, you're going to have a laugh.
Give birth to a calf, it's Conan.
This has been a Team Coco production.