Pete Holmes | Son of a Boy Dad #389

Summary

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Son of a Boy Dad #389: Pete Holmes

Podcast: Son of a Boy Dad
Host: Barstool Sports
Date: April 2, 2026
Guests: Pete Holmes, Ronny Chieng, Chris Fleming, Connor Mook

Episode Overview

This freewheeling episode brings on comedian Pete Holmes for a sprawling, comic, and insightful conversation with hosts and producers from the Barstool universe. Ostensibly structured as an advice sit-down for Lil Sasquatch (now going by Connor Mook after dropping out of college), the episode explores comedic craft, personal history, life transitions, and the idiosyncrasies of growing up with stand-up comedy as a calling. Alongside frequent jokes and irreverence, the hosts and Pete Holmes swap stories about the journey from open mic struggle to professional comic, touching on everything from DIY coffee obsessions to the psychology of performance, and from battle rap technique to meeting your heroes.

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Key Discussion Points & Insights

1. Coffee as Craft… and Comedy

• Elaborate Coffee Rituals
  Early on, the group riffs on their coffee habits, from expensive home espresso setups to the quasi-masculinity conferred by cortados.

  • Pete Holmes boasts about his ECM Synchronica machine and pokes fun at the "drip coffee" crowd.
  • This segues into a discussion about obsessive coffee routines, the economics of DIY vs. store-bought, and gadgetry (timestamp: 01:06–05:31).

• Quote:
  “You know what’s more fun than, like, trying shots and you’re getting ripped on espresso? You know, you get higher and higher and higher and they get better and better and better and cr. Different beans — it’s just such a fun, harmless hobby. It doesn’t make you fat, doesn’t make you stupid. It might make you a little paranoid.”
  — Pete Holmes [04:44]

2. Generational Differences, Maturity, and Comedy

• Youthful Carefreeness vs. Aging Preferences
  Pete reflects on how, at 46, he’s worlds away from the ‘wake up and eat pepperoni pizza at 7am’ phase:

  • “At some point, you’ll be 46 and you won’t even remember…you won’t even be able to get in touch with this guy.” [06:47]
  • Aging means refining preferences (“You get refined, but refined just means more preferences.”)
  • The hosts agree: their world is coffee and airline travel — the comic’s life [07:29].

• Travel and Comic Lifestyle
  The "airline and coffee" joking leads to reflections on the grind of touring, and how good coffee and travel habits are survival skills for comics on the road.

3. Comedy Origins & Digital Breaks

• Connor’s Story: From Twitter to Barstool

  • Dropped out of college after Barstool offered him a job for his precocious comic voice on social media.
  • “You’re the Zuckerberg of dick and fart stuff.” — Pete Holmes [08:41]
  • Explores the non-traditional paths in comedy and how digital platforms have changed comedic career trajectories.

• Meta, POV, and Creepy Tech

  • Discussion on using Meta glasses to film coffee routines quickly devolves into the issues of POV porn, bans in Japan, and privacy concerns [09:25–10:35].

4. Sexual Undercurrents of Internet Success

• Observations on Social Media Virality
  Pete muses that everything huge online (Facebook, Instagram, etc.) has a sexual driver, which distinguishes the “things that go huge.”
  • “Why did Facebook go huge? Because people want to have sex…that’s why I’ll never be huge… My special will get no one laid.” [10:35]

5. Comedy Special Talk and Performing Vulnerably

• Recaps of Pete’s Specials

  • The group fumbles through which special contained which joke, but use this to discuss comedic style and the evolution of bits.
  • Notable: Pete’s bit about body language on stage (“protecting your neck”), and how posture communicates confidence or vulnerability [13:45–15:58].

• Quote:
  “If it doesn’t work and you just continue with the posture of someone who is doing well, that itself is a joke. It’s funny that you don’t care.”
  — Pete Holmes [15:58]

• Ownership of Onstage Mishaps
  Pete encourages embracing mistakes, making the moment the show:

  • “Whatever’s happening is the show right so if you miss...that’s funny. And if the joke doesn’t work, that’s funny in its own way.” [17:49]

6. Freestyling, Battle Rap, and the Art of Staying Calm

• Writing vs. Freestyling

  • Chris Fleming notes that battle rap is largely pre-scripted now, diminishing the “magic” of true freestyle, but raising the quality.
  • Pete draws a parallel with stand-up: the true skill is staying calm under pressure, not just the joke-telling [21:52–25:11].

• Quote:
  “So many times, the skill isn’t the skill...The real skill is staying calm and centered.”
  — Pete Holmes [22:26]

• Craft, Mythology, and Sucking at First

  • The group laments that creative process is mythologized (e.g., 8 Mile), but actually, everyone starts out bad.
  • “Making stuff is stupid. And we actually, if we’re honest, we don’t want to see it [the struggle]. We want a mythology.” — Pete Holmes [32:10]

7. Community & Comedy’s Cultural Ties

• Shared Suffering, Camaraderie, and Comic Bonding

  • Tales of comedy condos and open mics: disgusting living quarters, awkward roommate stories (notably, “Mook and toothpaste”), and how shared hardship fosters bonds [36:47–39:59].
  • “That does bind you together.” — Pete Holmes [69:18]

• Reaching Milestones: Passing at the Cellar

  • Ronny shares an emotional moment about getting "passed" at the Comedy Cellar, validating years of struggle. Pete vouches that the meaning you’ve charged a moment with is what you ultimately experience [56:57–57:42].
  • “You filled the toy box and then you open it, you’re like, look at all these toys. That was your heart that you were finding when you did it.” — Pete Holmes [57:42]

8. Meeting Heroes, Fame, and Performance Anxiety

• Meeting Comedic Heroes
  • Discussions about how meeting icons can go well or awkwardly; Pete shares a “Radio City Music Hall” story where doing a set for Dave Chappelle was strangely lonely and anticlimactic [62:18–66:44].
  • The psychological realities of fame — “Once you’re super famous, everything you do is a story.” — Pete Holmes [61:12]

9. Creative Process & Crashing Backstory

• Origins and Season Decisions for ‘Crashing’
  • Pete lays out how the HBO series Crashing drew from his real experiences, and how its series arc mirrored real comic struggle.
  • On its ending: “If we had done a fourth season… it’s not ‘crashing’ anymore, it’s flourishing.” [70:38]
  • Discussion on the kinship among comics, and how shared rites of passage become lifelong bonds.

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Notable Quotes & Memorable Moments

| Timestamp | Speaker | Quote | |-----------|---------------|----------------------------------------------------------------------------------------| | 04:44 | Pete Holmes | "You know what's more fun than, like, trying shots and you're getting ripped on espresso?...It might make you a little paranoid." | | 08:41 | Pete Holmes | "You're the Zuckerberg of dick and fart stuff." | | 10:35 | Pete Holmes | "Everything successful...things that go huge always have some sexual component." | | 13:45 | Chris Fleming | "But just explain the—the arms cross thing, just because I think more people deserve to know about that because it'll make you rethink how you carry your body." | | 15:58 | Pete Holmes | "If it doesn't work and you just continue with the posture of someone who is doing well, that itself is a joke. It's funny that you don't care." | | 22:26 | Pete Holmes | "So many times, the skill isn't the skill...the real skill is staying calm and centered." | | 32:10 | Pete Holmes | "Making stuff is stupid. And we actually, if we're honest, we don't want to see it. We want a mythology like Amadeus." | | 57:42 | Pete Holmes | "You filled the toy box and then you open it, you're like, look at all these toys. That was your heart that you were finding when you did it." | | 69:18 | Pete Holmes | "That does bind you together." |

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Timestamps for Important Segments

• Coffee & Masculinity Riff: 00:25–05:24
• Generational Musings, Travel, and Comedian Life: 06:33–08:01
• Connor’s Comic Genesis: 08:05–09:01
• Meta Glasses, POV Tech, and Privacy: 09:25–10:35
• Performance Anxiety and Bombing: 13:45–19:14
• Battle Rap/Comedy Skill Crossover: 21:52–27:36
• Shared comic suffering, Community, Comedy Condos: 36:47–39:59
• Comedy Career Milestones — Cellar Passing: 56:57–57:42
• Meeting Heroes & Chappelle at Radio City: 62:18–66:44
• Crashing’s True Ending & Creative Arc: 69:31–72:07

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In the Words & Tone of the Guests

Throughout, the conversation is loose, self-referential, often meta, and jokingly profane—a blend of dry insights, bravado, and vulnerability. Pete Holmes is reflective, warm, and capable of turning a joke about coffee into an existential observation on art and aging; the Barstool crew are irreverent, self-deprecating, and run with every tangent. The mood is always comedic but often wistful or subtly motivational, especially around the struggles and small victories of a comedy career.

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Final Thoughts

Pete Holmes' appearance delivers a crash course in the realities behind artistic success—the craft, the grindy camaraderie, and the ongoing process of self-definition. For aspiring comics or fans of comedy’s inner workings, the episode is rich in both laughter and lived wisdom. The hosts’ rumination on what it means to grow up, let go, and keep showing up provides the bigger thematic frame, with Pete’s story anchoring the experience.

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Pete Holmes’ new special "Silly, Silly Fun Boy" is out March 24th on YouTube. [77:26]

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Transcript

[Chris Fleming]

Hey. Son of a boy. Dad. Listeners, you can find every episode on Apple podcasts, Spotify or YouTube Prime. Members can listen ad free on Amazon Music.

[Pete Holmes]

I gotcha.

[Chris Fleming]

You got a big ass coffee today, bro.

[Pete Holmes]

A little local place I found.

[Chris Fleming]

Are we good to go?

[Pete Holmes]

Smallest look, I'll talk about whatever you want to talk about if you like lattes, but it's too much milk. Now I'm making it a guy thing. Too much titty milk, bro. Get a cortado. That's what this is. So it's an espresso with just a little bit of milk.

[Chris Fleming]

Nice.

[Pete Holmes]

So I see people drinking these fuck off lattes and I laugh at them.

[Chris Fleming]

You know, have a good laugh at

[Pete Holmes]

the guy who figured it out.

[Chris Fleming]

Their 1 ounce cup. Your shot glass.

[Pete Holmes]

Yes. I could fill this. I'm not going to make that joke at 9am it's like 8am My body's time. You know, he's.

[Chris Fleming]

He's like a coffee nut. He has like a $10,000 La Marzocco set up at home.

[Ronny Chieng]

Seven.

[Chris Fleming]

Seven. Seven five.

[Ronny Chieng]

Let's not get out of.

[Chris Fleming]

It's seven five. And with the Japanese, the ceramic mugs. Ceramic mugs.

[Pete Holmes]

I mean, I'm not ashamed to admit I think it's a wonderful hobby. I also have a. I have an ECM synchronica.

[Ronny Chieng]

Oh, well done. This I talk about.

[Pete Holmes]

Is this real? Then everyone just turned it off.

[Ronny Chieng]

Go re.

[Pete Holmes]

Listen. No, no, I'm sure Shane. See, that's why Shane, he's brilliant and he appeals. He's a drip coffee motherfucker. And I'm out here going like, you guys tamp it. And everyone's like, well, that will never be as big. Will never be as big.

[Ronny Chieng]

I saw him at Madison Square Garden and I thought, I need to invest in coffee. You mean this is unattainable? I need a. I can't do this.

[Pete Holmes]

I should lean into my coffee habit.

[Ronny Chieng]

Yeah. Clearly this pursuit I'm in has reach a. A ceiling.

[Pete Holmes]

Are you. So noodles. Are you sober? Oh, so noodles. Now you're. Now you're on my podcast.

[Ronny Chieng]

Yeah.

[Pete Holmes]

Guess what? You're on my podcast, by the way.

[Ronny Chieng]

We've begun. Is that okay?

[Pete Holmes]

Of course.

[Ronny Chieng]

Okay, great. Great. I'm not sober. He is, though.

[Pete Holmes]

I'm only asking because sometimes people get real into coffee when they can't put other liquids in their face.

[Ronny Chieng]

You're looking for divorced, which I am. Divorce works. Yeah. Sober without child.

[Pete Holmes]

Yeah. Yes. See, I have the lifestyle of a divorced, childless man. And I'm married with a child still out there. Tampa.

[Ronny Chieng]

I wish.

[Pete Holmes]

Do you use the three little. The needles.

[Ronny Chieng]

The Weiss distribution technique? Yes. A WDT tool? I do, yeah.

[Pete Holmes]

Is yours going on it and spinning are.

[Ronny Chieng]

You know, that's cool. There are some cool ones like that. The Weber workshops. One my favorite. It's the Moonraker 500.

[Pete Holmes]

Are these sponsors? No, not at all. No. Anything being gained from.

[Ronny Chieng]

I've reached out to every one of these brands and been like, hey, making coffee. And they're like, we found that our price points are too high for influencers.

[Chris Fleming]

True.

[Pete Holmes]

I, I whole latte love. I had them on. Not, I don't want to say on the hook, but I, I had a zoom with them and they were going to sponsor my pod and, and then the pandemic happened. That's when we should have tripled down. That's when people got into weird baking bread and needles and the thing. We'll talk about it off mic. I don't want to bore everybody.

[Chris Fleming]

No, this is what this show is.

[Pete Holmes]

I know, know, but I can see, look at your body language.

[Chris Fleming]

You're like, it's open, it's open. You're closed off. Like you're ashamed of your coffee.

[Pete Holmes]

I'm ashamed of. I'm just like seeing a resigned. He's doing it again. I'm here for Body's Beautiful.

[Chris Fleming]

I'm the documentarian of all of his.

[Pete Holmes]

Okay, well, let's. If you want to talk about. I'll talk about it endlessly. But I am having some issues.

[Chris Fleming]

Does it make it hard to drink like a store bought coffee? Because I feel like that's why you got into the game of a homemade. Because you didn't want to be that.

[Ronny Chieng]

And, and I liked, I liked saving money on not buying a coffee every day.

[Pete Holmes]

And you just paid it up front.

[Ronny Chieng]

Like the lottery.

[Pete Holmes]

Like a lump sum.

[Connor Mook]

Yes, but, but you know, your lifetime supply coffee.

[Pete Holmes]

I'm going to put seven, five in

[Ronny Chieng]

the machine in, in, in 2038. I will have broken even.

[Pete Holmes]

Wait, is that really. Are you. I don't feel like you're being honest.

[Ronny Chieng]

No.

[Pete Holmes]

So like with yourself.

[Ronny Chieng]

I. Well, I originally, seven years ago I bought a Breville and, and it was like a starter machine, whatever. And I would say that over the course of those seven years, like I must have saved, you know, thousands and thousands of dollars versus buying like an $8 latte or whatever at a nice coffee shop.

[Pete Holmes]

I take it back. I think you are being on it. I, I just thought maybe most people that buy these things just love the tinkering and the dialing. It in. And. And then. You know what's more fun than, like, trying shots and you're getting ripped on espresso? You know, you get higher and higher and higher and they get better and better and better and cr. Different beans. Like, it's just such a fun, harmless hobby. It doesn't make you fat, doesn't make you stupid. It might make you a little paranoid. Think there's a sniper on the roof. My man. My man.

[Ronny Chieng]

Okay, sorry.

[Pete Holmes]

Forced it. I. Yeah, it's a pretty benign hobby. It is, but the money saving, that's why I'm like. I don't know if that's the most alluring thing, but it is a perk.

[Ronny Chieng]

I think that that applied more with my cheaper machine. Now I've invested so much that that. That reasoning falls a bit short.

[Pete Holmes]

You drink it plain. See, I drink cortado, as I was yelling at you guys earlier, because I think lattes have too much milk in them. Yeah. But when I make it at home or if I go to a nice place, I'll just get espresso because I like. I'm that guy. Yeah, like, taste you too, To.

[Connor Mook]

No, no, I'm not an espresso. I can't really drink a lot of coffee. I freak out.

[Pete Holmes]

Nice.

[Ronny Chieng]

Yeah. So he drinks energy drinks.

[Connor Mook]

Yeah, I'm drinking a coffee right now, but that's probably as far down energy drinks. I do. Yeah.

[Pete Holmes]

I wonder what they do to that to make. Is it L. Theanine?

[Connor Mook]

I think so. Yeah.

[Pete Holmes]

Bro, I just took. Bro, I just took some L theanine with my coffee, so.

[Ronny Chieng]

Oh, yeah, that's.

[Pete Holmes]

That's a nice little.

[Chris Fleming]

Wait, what does healthening do? I don't know.

[Pete Holmes]

Really evens out coffee. Sorry.

[Connor Mook]

Yeah.

[Pete Holmes]

Too excited now you're.

[Connor Mook]

You're dead on it. Yeah.

[Pete Holmes]

If you take out theanine with your coffee. Hi, I'm Andrew Huberman. If you take out theanine with your coffee, it evens it out. It's really nice.

[Ronny Chieng]

So why not?

[Connor Mook]

Just keeps you calm.

[Ronny Chieng]

Well, how old are you?

[Connor Mook]

I'm 24.

[Pete Holmes]

Yeah, you're still in your. Like, Red Bull.

[Chris Fleming]

Yeah, yeah, yeah.

[Pete Holmes]

Do it.

[Connor Mook]

Exactly.

[Pete Holmes]

It's killing your sperm.

[Connor Mook]

You destroyed me. It broke my stomach.

[Ronny Chieng]

Harry's morning routine starts at a gas station.

[Pete Holmes]

Wow.

[Ronny Chieng]

That's where he goes, get ready for the day.

[Connor Mook]

Get a Cliff Bar. Cliff Bar.

[Pete Holmes]

You're gonna wake up. Well, that's not true. Life is long. I do not feel like I just woke up and I was 46. But at some point you'll be 46 and you won't even remember. Like, you won't even be able to get in touch with this guy. Yeah, yeah, the guy that just was like, ah, pepperoni pizza. I'll get it at seven. Like, enjoy it. It's so carefree. How old are you?

[Ronny Chieng]

36.

[Pete Holmes]

Okay, so I'm older than both of you, but, like, still, like, you're getting there. Like, you get refined, but refined just means more preferences. Like, enjoy this. Like, Bart Simpson. Like. Like, who cares? Roller skating. Weaner out. Like, do a loop. Like, it doesn't matter. Y. Yeah, yeah. Middle seat coach. You don't even notice.

[Chris Fleming]

See, that's our other topic. That's our other thing.

[Ronny Chieng]

You got your thumb all over the pulse of this podcast, brother. You don't even know the waters we're wading into.

[Connor Mook]

Pretty much all we talk about is coffee and airlines, airline travel.

[Pete Holmes]

Okay, well, those are my two Status PD treaties.

[Ronny Chieng]

Yeah.

[Pete Holmes]

Like, I do good coffee and I do good travel. Because if you're a comic.

[Ronny Chieng]

Yeah, yeah.

[Pete Holmes]

It'll. It'll wreck you.

[Connor Mook]

Yeah.

[Pete Holmes]

And you must be. You've been a comedian for, like, seven, eight months. I mean, it must be grinding you the head to pieces.

[Connor Mook]

I've been doing for, like, five years now.

[Pete Holmes]

Wow.

[Ronny Chieng]

He's a touring headliner, though. He's got good crowds, incredible social stuff.

[Pete Holmes]

Did you, like, pop off?

[Connor Mook]

I. I did, like, Twitter when I was, like, really young. Like, when I was in, like, middle school.

[Pete Holmes]

Shelby Pharaoh over here. I'm sorry, I didn't realize that Shelby.

[Chris Fleming]

Shelby Pharaoh is a crazy poll. Shelby Pharaoh is a sick poll.

[Connor Mook]

I love that.

[Pete Holmes]

You got it. Shelby's very funny. Okay, that's cool. So, yeah, Twitter kind of picked up,

[Connor Mook]

and then I got hired here when I was, like, 19, I think.

[Pete Holmes]

Nice.

[Connor Mook]

And then I moved to New York, and I started doing stand up, like, right when I moved here.

[Chris Fleming]

Good friend. He dropped out of college because Barstool offered him a job. He was precocious. He is precocious.

[Pete Holmes]

You're the Zuckerberg of dick and fart stuff. I'm like Mark Zuckerberg, but dick and fart stuff. But I do write wakeboards. Is that still, like, a hip riff?

[Chris Fleming]

Yeah.

[Pete Holmes]

Okay. I'll be leaning on you big time, Zuck, to see if I'm still relevant. Are you guys sponsored by Meta?

[Connor Mook]

No. I wish. That would probably fucking pay the bills. Yeah, Meta sponsorship.

[Ronny Chieng]

I've been filming my. My morning workflow at my La Marzoca Linea Mini Micro. Excuse me. With my Zerno Z1 grinder with flappers. And, well, the high. Anyway, the point is, I understand that I've been using the meta glasses for that. Are those. I owe you those. Those are yours, by the way. I owe them back to you.

[Pete Holmes]

Oh, you've been filming it with your glasses.

[Ronny Chieng]

Yeah.

[Chris Fleming]

So he can get his, like, hands in and everything.

[Pete Holmes]

Yeah.

[Connor Mook]

It's like you're playing a video game.

[Pete Holmes]

I see Everything comes back to porn. First meeting, they were like. And POV porn is now.

[Ronny Chieng]

You're completely Right.

[Connor Mook]

I'm pretty sure that's like. There's like something going on with that right now.

[Chris Fleming]

What?

[Connor Mook]

Meta with the glasses. Like they're banning them or some.

[Ronny Chieng]

Oh, really?

[Connor Mook]

I mean, yeah.

[Pete Holmes]

Well, it's like in Japan, there's a real peeping problem then.

[Chris Fleming]

That's why they have the sound on the shutter.

[Ronny Chieng]

That's right.

[Chris Fleming]

So you can't be sneaky. You can't with the upskirts.

[Pete Holmes]

That doesn't make a sound when you take a picture.

[Ronny Chieng]

Yeah.

[Pete Holmes]

I'm sure somebody knows a guy if you're in Japan.

[Connor Mook]

Yeah.

[Chris Fleming]

And so that these glasses have, like a light that kind of flashes, but I think you can get off brand or soup them up so they don't.

[Pete Holmes]

So they're going to be bootlegging and flashing. Filming your. Exactly, exactly. The thing that made you is going to kill you.

[Connor Mook]

Exactly.

[Chris Fleming]

Wait, so why are they. Why are they banning them, though? People are using them for.

[Ronny Chieng]

For porn or for band. Guys are wearing them on their shoes on the subway.

[Chris Fleming]

Ankles full of glasses.

[Ronny Chieng]

Whoopsie daisy. She's on a skirt. Yeah, there you go. Oh, no.

[Pete Holmes]

Yeah. Everything successful. Like, things that go huge always have some sexual component. Like, like, obviously Facebook is. Is the. But like, why did Facebook go huge? Because people want to have sex. Instagram becomes about sex. And. And Instagram become AI. Become exactly like. That's why I'll never be huge. Because my. My special will get no one late. The guys that are watching my special are like one minute and they're like, finishing the special while their girlfriend falls asleep.

[Ronny Chieng]

I. I watched years ago. I loved little glaze here for a second. I loved.

[Pete Holmes]

Is that a term?

[Connor Mook]

Glaze? Yeah, it's like sucking off.

[Pete Holmes]

Oh, nice.

[Chris Fleming]

Yeah. He's going to suck you off.

[Ronny Chieng]

It's a little counterintuitive.

[Pete Holmes]

Anything. Put on the glasses.

[Chris Fleming]

You'll be.

[Ronny Chieng]

You'll be glazing me. Oh, yeah, that's how it should work.

[Pete Holmes]

We're going to be co glazed.

[Ronny Chieng]

Yeah.

[Pete Holmes]

Give her.

[Ronny Chieng]

I will elicit glaze. I will summon glaze. No, but I watched your HBO Special. And I love. I watched it twice.

[Pete Holmes]

Which one? Yeah, yeah, yeah.

[Ronny Chieng]

I don't know the name, but it had the blue background. And I'll tell you jokes that I remember.

[Pete Holmes]

It was pretty clean.

[Ronny Chieng]

Yeah, it was. I loved the Unicorn. Unicorn.

[Pete Holmes]

Oh, silly. No, that's Faces and sounds, I think that's right.

[Ronny Chieng]

That's what it was. And then I loved the Street Fighter Fighter Japan joke.

[Pete Holmes]

That's my Comedy Central special. This is boring. Nobody knows.

[Chris Fleming]

Is that the one where, like, the, like, a tiger, like, slashes your stomach or something so people have their, like, body?

[Pete Holmes]

That's. That's.

[Ronny Chieng]

This is.

[Pete Holmes]

Nobody cares about this. Pete tells you which joke was from.

[Chris Fleming]

But I just. I've. I've always thought about that.

[Pete Holmes]

Faces and sounds.

[Chris Fleming]

I think about that every time. I, like, cover my, like, my innards like this. Do you know what. Do you know what joke I'm talking about?

[Ronny Chieng]

This is the Street Fighter stuff, is it?

[Pete Holmes]

No, it's not. This is about why. Sorry, I love you, and we're going to get to it. I'm very sure that's on.

[Ronny Chieng]

I feel like I have a better sense of your material. You actually might overtake.

[Pete Holmes]

Actually might. I think that's on. Nice try. The Devil, which is the Comedy Central special that has a Blue battle background. And why would you know? Nobody cares what network and is on anymore. Like, you just saw, especially. I'm glad you watched it. I'm glad you like it.

[Ronny Chieng]

I feel somewhat sure that the one that I really loved was on HBO because I came to it through crashing.

[Chris Fleming]

You came to.

[Pete Holmes]

And you.

[Ronny Chieng]

You got that special, like, while you were doing crashing, right?

[Pete Holmes]

Yeah. And that was pure Judd, by the way. They passed hbo. Pat called them, and it was like, he has a show on your network. Like, you're gonna have his special be on Netflix while he has a show. And to their credit, they were like, you're right. Yeah. Like Judd and Conan. All these guys that have helped me out are, like, just so wonderful. I just like sharing that. It was obviously in my benefit. But, like, there are people out there in show business that, like, care and. And help and pay forward, and I like giving them a little shout out.

[Ronny Chieng]

That's cool.

[Pete Holmes]

Yeah.

[Chris Fleming]

But just explain the. Explain the. The arms cross thing, just because I think more people deserve to know about that because it'll make you rethink how you carry your body.

[Pete Holmes]

Well, it's funny you pointed out that language is open. Right. This is like a confident person or someone.

[Chris Fleming]

I didn't say confident.

[Pete Holmes]

Yeah, but, you know, like, taking up space. Don't do it on the subway. The man spread. But, like, this is a confident thing because I'm not worried you're going to attack me. Like my groin is exposed.

[Chris Fleming]

Yeah, yeah.

[Connor Mook]

Similar to, like a cat.

[Pete Holmes]

Similar to a cat. Yes, my man. But my neck. The neck is so. I love that you remember this bit because this was not just a bit. It was something that somebody explained to me or, I don't know, saw it on the Discovery Channel. It's real, like anthropology stuff. Like, if you cross your arms, what you're doing is protecting yourself from a kill stroke. If somebody hits you across your gut, you're dead. Like, if a lion swipes you here, you're dead. So it makes sense. If you're nervous, you cross your arms. You want to protect yourself. You already have ribs. Ribs are getting the. But, like, this is vulnerable. This is smushy, not on you.

[Connor Mook]

No, it is. It is. Okay.

[Pete Holmes]

Red Bull, Blueberry. Red Bull Blueberry. The that's exposed is your neck. No rib cage here. Right there can't be the way that it's mobile, like the new Batsuit Dark night on. You got a very soft, vulnerable neck. So your shoulders go up, right? Your shoulders also go up when it rains. I don't know why, but if you're scared, this is your position and it makes perfect sense because your neck is everything you need to be alive and nothing's guarding it. So you put your neck up. And that's why. This is what made it a joke. This is why so many standups are up there like this. Hey, what's going on with these new Triscuits? Garlic and herb. How about just herb? You know what I mean? Like that. Because they're freaked out. And I like to remind myself something. It's not just to, like, flex. It's to tell the audience that they can relax, right? Assume the posture of someone who's comfortable. It's not really like confidence, like, go sell it. It's like, just show them, like, you're not worried. Especially if you're bombing. Especially if a joke doesn't work. That's something Hannibal Buress taught me. He said explicitly, if he tells a joke that doesn't work, the comics instinct is to look down. And it is. You go, like, what's the employee discount at the dollar store? You think it's just take it. I tell one of my good jokes, but then, like, it bombs.

[Ronny Chieng]

And then.

[Pete Holmes]

And then you kind of like, what else? You look at your notes. That's also protecting your neck. You're like, you're closing off, but if you. If you. If it doesn't work and you just continue with the posture of someone who is doing well, that itself is a joke. It's funny that you don't care. Why do you like. Shane Gillis is a good example. Could that dude. He. He. He's engaged with the audience, but he's just kind of like, this is what I like. This is. This is what I like. You know what I mean? Like, and that's alluring. People are drawn to that.

[Chris Fleming]

Another thing that I've noticed that people do, because I think people are aware of this, but sometimes dudes will get. They'll do, like, the inverse of it, and they'll have, like, a hand behind Nate, which I think the Napoleon. And I do think that.

[Pete Holmes]

That Nate is looking at a map of the world going, like, Poland, Venezuela will be bargain. I love Nate. We started to go.

[Chris Fleming]

Do you think that's like, an analogous, like, physical response? Do you think that it's linked to the same thing where it's like, you don't want to be like this, but you're like, I subconsciously. Or what do you think it is?

[Pete Holmes]

I know Nate a little bit. I love him to death. I think I can hear him saying, like, I just didn't know what to do with my hands.

[Chris Fleming]

Yeah.

[Pete Holmes]

And he doesn't want to think about it. And he's not Chris Fleming, who's brilliant, who's using his body. Nate is like, don't worry about my body. Please don't worry about it. So he poses like George Washington. It's funny that his most famous sketch is the George Washington sketch, and he kind of stands like he's wearing a powdered wig. But I think that's just a way of being like, if he had chosen this, somebody would have been like, you should stop doing that, because this does look. You literally have your hands behind your back. You're like, I'm not worried about you.

[Ronny Chieng]

I've started putting my left hand in my pocket, and I don't know if that's a good idea or not.

[Pete Holmes]

I love hand in pocket.

[Connor Mook]

I put my hand in my pocket. But then sometimes I'll go to, like, I'll take it out, and then I'll go to put it back in, and I'll miss. And then I just, like, have, like, one finger in my pocket.

[Pete Holmes]

Can I look? You don't need advice. You're doing great. But something that really clicked for me with standup is whatever's happening is the show right so if you miss. I'm not saying you have to riff on everything.

[Chris Fleming]

Yeah.

[Pete Holmes]

But, like, that's funny. And if the joke doesn't work, that's funny in its own way. Like, if you're sweating and bombing, that's funny in its own way. And there's this, like, reclaiming of, like. Like. Like, one time I accidentally hawked a loogie on my wrist when I was starting here in New York, and I just ignored it. Now, if that did. That's all I would talk about.

[Connor Mook]

Yeah. Yeah.

[Pete Holmes]

How we're all just bags of fluid, and it's so embarrassing. And it's a wonder things like this don't happen more often. But, like, back then, I was, like, frozen and just watching, like, a slug move up my hand. It was disg. But now I'm like, just. Just. Just own the moment. Just own what's happening. It seems like you've already figured this out.

[Connor Mook]

No, no, no. I appreciate that.

[Chris Fleming]

I feel like I kind of like I really hijacked what you were trying to do.

[Ronny Chieng]

I have no idea.

[Pete Holmes]

You were talking about The Street Fighter 2 sounds, which we don't know or care which one that is on. Even though I'm pretty sure I'll give

[Ronny Chieng]

you one more joke from this special, which was that bit you did about sleep.

[Pete Holmes]

Well, that is the HBO special.

[Ronny Chieng]

There you go. That's. I think that is the one you might have watched.

[Pete Holmes]

I've been wrong before.

[Ronny Chieng]

Unless I. Maybe I watched a couple at that.

[Pete Holmes]

No, no, no.

[Chris Fleming]

I.

[Pete Holmes]

Let's move on. Because I just look stupid and nobody cares. But I'm.

[Chris Fleming]

I'd like to see you guys argue about this

[Pete Holmes]

again. I am turning this into my podcast. I'm like, let's move on.

[Ronny Chieng]

I have a question for you.

[Pete Holmes]

Yes, sir?

[Ronny Chieng]

Would you research the podcasts you jump on before you jump on them? Like, did you know what you were getting yourself into today?

[Pete Holmes]

No. What is this?

[Ronny Chieng]

This is it.

[Connor Mook]

Yeah. This is really.

[Pete Holmes]

No, I know it's a podcast, but it's called Son of a Boy, Dad.

[Connor Mook]

Yeah. Yeah. That's a little bit more. There's not a big explanation for that, unfortunately.

[Pete Holmes]

This is. This is your. Well, I'm trying to think. I have things like that. I called my book Comedy Sex God, and every interview about it started with, like, why is it called Comedy Sex God? So I'll spare you that, but now

[Connor Mook]

I'm dying to know.

[Pete Holmes]

Those are the three topics it's about.

[Connor Mook]

Understand?

[Pete Holmes]

Did we list them in that order? Because it's kind of funny. Yes. People were like, so you're on the Today Show. So you're a sex guy. Neglect here, but yes. I. I don't research it, but I've done other barstool shows and especially with comic. What do you do? What do you do? What the do you do? Pete Holmes loses it.

[Chris Fleming]

No, I just really just glean off both of their success and just kind of just balance it out in the middle.

[Ronny Chieng]

Try this on for size.

[Pete Holmes]

Pete Holmes, you host this podcast. Yeah, yeah, that's called hosting.

[Connor Mook]

He does a bunch of stuff.

[Ronny Chieng]

Champion. Champion battle rapper. No joke.

[Chris Fleming]

Yeah.

[Pete Holmes]

Fascinating.

[Ronny Chieng]

As good as their episode.

[Pete Holmes]

Fascinating. I know. That was such a corny thing to say.

[Ronny Chieng]

Father of twins, if I may.

[Chris Fleming]

Please, please.

[Ronny Chieng]

Father of new twins.

[Pete Holmes]

Father of twins.

[Chris Fleming]

Twin. Twin boys. And that's.

[Ronny Chieng]

It makes the most money of the three of us.

[Connor Mook]

Is a big one.

[Chris Fleming]

That can't be true.

[Ronny Chieng]

So he is the most successful.

[Connor Mook]

I lead with that.

[Pete Holmes]

I watch Harry Mack videos and I get emotional. I love him.

[Chris Fleming]

I mean, that guy is an insanely talented individual. Yeah.

[Pete Holmes]

It's almost weird that he's never. I've never even seen him buy time. Really. Every once in a while he'll say, like, h. Mac, you know, right off the dome. Like some line where he's got a crush.

[Chris Fleming]

It's a crutch. Yeah, he'll use a crutch. But he's mostly crutchless.

[Pete Holmes]

Mostly crutchless, yeah. And the higher stakes the situation, the better he seems to do. He's one of those, I hope similar to comedians. Pressures on you do better. Like that's the inverse. Most people pressure's on. They do worse.

[Chris Fleming]

I think freestyling the way that he does is tantamount to speaking a different language where you have to translate inside your head while simultaneously saying something different. So he's getting to a rhyme scheme and then at the same time saying different words out of his mouth. Like thinking and thinking while talking. Thinking while talking.

[Pete Holmes]

Yeah. That is a huge one time. This is embarrassing, but I think that's my skill too. Yeah. I can't freestyle. I like to freestyle in my car if I'm being. I'm very relaxed. I think. I think the real skill of freestyle looks. Look, don't let me tell you. Is lowering your heart rate. It's the same with magic. It's the same with stand up and swimming underwater. And swimming underwater. And also pretending you're dead so you can reunite with your star crust lover. Do you get that reference? Romeo and Juliet. Romeo and Juliet.

[Connor Mook]

Of course I did.

[Chris Fleming]

I did.

[Connor Mook]

Yeah.

[Pete Holmes]

That's high school.

[Connor Mook]

Yeah, I think it should have been middle school.

[Pete Holmes]

100% JK. But, like, so many times, the skill isn't the skill. Like, freestyling is the skill, but the real skill is staying calm and centered. Because, like, when people are like, oh, my friend Jeremy is so funny, he should do comedy. I'm, like, being funny. Writing jokes is part of it, but it's actually showing up and lowering your heart rate and being calm when you're really, really under a lot of pressure. The other thing that I think is super important for comedy is having a compulsion. So I'll do a set, and that night, my brain is just working on it. Like, I never say work on that, but, like, you know, when you tell your computer to defrag or like, clean up or whatever, just runs for a while. After I do a set, after we all do sets, that's what our brains are doing. That's actually the secret sauce of being a standup. Because if. If it was just down to, like, what we will ourselves to do and, like, sit at the desk and grind on the jokes, I don't think most of us do that, but our brains are constantly refining. You didn't even write it down. That part didn't work. Next time you're doing it, you just dropped it. That's the skill. And staying calm is the skill. So freestyling. If I'm freestyling in the car, you ever get on a run by yourself and you're like, jesus Christ, this is amazing. If anybody could hear this, and you're like, impressing yourself, like, what? Because, you know, it's like, it's obviously, it's free associating, and it goes this interesting place, and then it ends where it began. And you're like, if anyone who cares, the skill is doing it. Going back to the funny friend Jeremy, I'm glad you're funny, but the skill is doing it. At 8 o'clock on Saturday, Stel Blue

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[Pete Holmes]

A lot of people are funny. Be funny now. I'm not in the mood. I'm scared. There's drunk people. Well, that's. That's what makes it a thing. That's. That's why I'm incredibly impressed.

[Chris Fleming]

It's so fun. I mean, it's. And well, now battle rapping is. It's written so it's not even. I mean, there's some freestyling, but for the most part, it's like you write it like a. Like you would write a script for a play and you memorize it. Yeah. Does that make it less impressive?

[Pete Holmes]

Yes, of course it does that. Absolutely. That ruins it. If I've done that. If I could write a rap about each of you, give me 30 minutes. Don't make me do it. But like, I'd come back and what rhymes with Armie Hammer? Redhead fucking scammer, you know what I mean? And do it. That's. It has to be off the dome.

[Chris Fleming]

But the quality of the material, like, skyrocketed once people could prepare it beforehand as opposed to the extemporaneous nature of what it was like when it was only on a beat in freestyle.

[Pete Holmes]

Well, I'll talk out the other side of my face because I just said it ruins it. But I'm also, like. I could see how that would elevate it because you are leaving behind a lot of brilliant people who can't necessarily do it on the spot, but if you gave them five, 10 minutes, they could really nail it and really do something better. So are we going to hit a ceiling with what is like true freestyleable? Yeah, probably. Harry Mac's probably there. And then like, maybe we will be like, take 10 minutes, take 30 minutes.

[Ronny Chieng]

But not to. I mean, the freestyling thing nowadays, like, I mean, we've talked about the formula. It's. You think to the second line of the couplet and just, you know, your punchline beforehand and then you put right.

[Chris Fleming]

You would have started with redheaded scammer and then ended on Army.

[Pete Holmes]

Right, right, right.

[Ronny Chieng]

Because, you know, you want to do a joke about Armie Hammer. So if you can think one line ahead, I'm. By the way, I'm not saying this is easy, but like, yeah, yeah, yeah, that's why anytime you hear a guy like that, like, the first line of the two is not funny. It's just a throwaway.

[Chris Fleming]

That's a setup.

[Ronny Chieng]

Yeah, yeah, it's a setup.

[Pete Holmes]

That's the muscle that you guys are working. It's like, okay, I have it. And comedians do that as well, just way less urgently. You know what I mean?

[Chris Fleming]

Like, how so?

[Pete Holmes]

Well, if you're doing crowd work and you have something great, you might think of it right while you're talking to them, and then you're going to wait and see how they are. And if they're a dick, you'd be like, all right, redheaded, Armie Hammer, go eat your girlfriend. Or whatever it might be.

[Connor Mook]

You'd walk them to it.

[Pete Holmes]

Yeah, but you wouldn't start with it. But we're doing it, like, more in a relational way, I suppose. I don't know. I think more accurately to your question is like, you know the funny part, and you're just gonna save it to the end. Just like an intro. Like, I know your name. I'm gonna say, save it to the end. And the amateur who introduces you says your name up top.

[Chris Fleming]

Yeah, that's smart. Yeah, that's pretty brilliant. It is. I mean, it's a great discipline, but there's just no money in it. And it's just like, oh, really? A nasty. A nasty. Just like a scene that eats itself.

[Pete Holmes]

Well, you know what I think is you tell me, and I'm really interested. It feels like impressions, but impressions are easy, like, easier. Like, if you can do an impression. Like, I just had Taran Killam on my podcast. He does this Brad Pitt impression. I didn't get the sense that he got nervous if I was like, please do your bread pit. Please do it. He just does it.

[Chris Fleming]

Right?

[Pete Holmes]

But when you. And I'm not gonna ask you to freestyle because I think that's a performer wouldn't do that to another performer. But I feel like when you say I'm a freestyler, all these fucking moms in their chunky night out jewelry are just like, do one, do one. And it sucks. Like, is that a burden that it is?

[Chris Fleming]

It's like, would you ask, like, a basketball player to, like, dunk in front of you? Like, you play basketball. Like, dunk, dunk for me.

[Pete Holmes]

Right? Well, this is why I get this. Like the comedian, you know, I'm doing Colbert later today. I like it. But Chris Rock made this point. A comedian goes on a late night show. People want him to be funny. Tom Hanks. I Don't know. I picked Tom Hanks. He's very funny. But I'm just like, an actor goes on. No one expects them to be, like, acting or, like, do it for me. Now we do what we do. I prefer that, but there is that slight burden. But like, I'm also, like, when doing this podcast. So you made fun of my we coffee. Right. I had this out of fucking respect right before the show and I took my L theanine right before the show. I'm priming myself and I'm. And you know, if I'm being honest not to dissect it too much, I'm thinking about like, okay, Pete, how do you want to come off? Be gracious, be interesting. Just a couple words. Be grateful, be funny, be alert. I'm trying to be the guest that I want to be on my own show. Like, show up. Right. I think about that priming just a little bit. If somebody's gonna ask me to freestyle, like, I love Eminem when they're doing those freestyling videos. They're doing their own version of all of that. They're taking their Adderall or whatever it is. They're taking their caffeine. They might go for a walk around the building, get their heart rate up. They might be jumping up and down, like, just going like, freestyle is like a fundamental misunderstanding in what being a performer is. Being a performer is conjuring up a state.

[Chris Fleming]

Yeah. Stretch a little bit on demand.

[Pete Holmes]

Yes. And it's not just like, I tried to do this joke where I was like, I think it's so funny. We see people when they're good, but everybody that was. Is good was bad. Yes. We erased this, but the first time Marshall Mathers freestyled, he wasn't good.

[Chris Fleming]

It sucked.

[Pete Holmes]

It sucked.

[Connor Mook]

He threw up in the bathroom.

[Pete Holmes]

He vomit on his sweater already. It was mom's spaghetti.

[Chris Fleming]

That's his thing.

[Pete Holmes]

He was nervous, but on the surface he looked calm and ready. But he went out and I'm not trying to take anything away from him. I know Donald Glover a little bit. One of the coolest people in the world. And when I listen to Childish Gambino and he's like, y', know, like a sound like that. Yeah, that. Yeah. Which is cool. It's a little sexy. It's a little fun. Right. There were five other things that they tried. They were like, nah. Because that's what it fucking is. Which is why every biopic sucks when it's Elton John being like, rocket, rocket boy. It fucking sucks when Queen is sitting around and someone goes, it's fucking stupid. No one wants to see it. That's why we mythologize. And 8 mile, you referenced 8 mile, right? He's never bad in 8 mile, but every comic, even Dave Chappelle, who they're like, he went up and he was amazing. I bet he was charismatic and magnanimous and interesting and better than 99. But he wasn't as good as he is now when he was. Whatever he was 15. Yeah, he might be the exception, but everybody else fucking sucks.

[Chris Fleming]

Sucks. For a while.

[Pete Holmes]

It's just. That's what we tried to show in Crashing. We were like, it's jokes about road signs. And you have, look, I'm sure you're different, but when I was 24, I was like, orange tic Tacs. Why do I want my breath to smell like I just had a tangerine? Isn't that just another food?

[Chris Fleming]

That's good, that's good, that's good, that's good.

[Pete Holmes]

I write it down. You guys are all worried about it, but this is why biopics are fucking stupid. Because making stuff is stupid. And we actually, if we're honest, we don't want to see it. We want a mythology like Amadeus.

[Ronny Chieng]

You don't know what the fuck that is.

[Pete Holmes]

But Mozart, there's a movie about him, it's called Amadeus. I'm just teasing it, but, like, he was like, oh, I just can't stop writing these symphonies. It's not how it was. It's not true. That is. There's many, many unfinished symphonies. Mozart's work is covered in redos and scratch ups. We tell the story. We want to think everybody's a genius. I just can't help it. Fuck off. Fucking offensive to true creatives because we know it's embarrassing, it's stupid, it's humiliating,

[Chris Fleming]

and that's kind of the fun part. In retrospect, I think if you look back to the times when you sucked ass and you're with a bunch of other people that sucked ass.

[Pete Holmes]

Couldn't agree more. That's why I was like, enjoy your Red Bull 7:11 pizza time. And you'll never be more with. With other people than at the beginning. Then you, like, you know, Lord willing, I don't know what phrase to use here, but, like, let's say some of you become professionals and start touring. Then you're, you know, you're in a nice hotel by yourself.

[Connor Mook]

Yeah.

[Ronny Chieng]

Dumb.

[Connor Mook]

Yeah. Sucks.

[Pete Holmes]

It can. It can suck. I bring my opener. Matt McCarthy, he's one of my best friends. That's a huge.

[Connor Mook]

Yeah, that helps.

[Pete Holmes]

That's a huge help.

[Ronny Chieng]

Yeah.

[Connor Mook]

Yeah. I bring my buddy Mook.

[Pete Holmes]

Mook. Mook.

[Connor Mook]

Yeah.

[Pete Holmes]

How old's Mook?

[Connor Mook]

Mook is 28.

[Chris Fleming]

Okay, this works.

[Pete Holmes]

Yeah, you don't want to bring like a 52 year old guy that hates your success. Oh, yeah, yeah.

[Ronny Chieng]

We're at different hotels.

[Pete Holmes]

All right.

[Ronny Chieng]

That episode of Crashing where you went out and played, I think it was bananas in New Jersey with Dove Davidoff and Jamie Lee, right?

[Pete Holmes]

Yes, yes.

[Ronny Chieng]

And you stayed at the comedy condo.

[Chris Fleming]

Yes.

[Pete Holmes]

Oh, yeah. Yes. I remember very vividly because when you, when you do a show, they'll scout locations and they show you pictures or maybe video. And I had such a firm idea of what the condo should look like because it was this amalgamation of every condo I've stayed in and none of them were gross enough.

[Ronny Chieng]

The Zany's Nashville Denver Comedy works. I'm doing there this weekend and they put me in the comedy in the condo.

[Pete Holmes]

Yeah.

[Ronny Chieng]

And I, we stayed there.

[Connor Mook]

I, I didn't stay.

[Ronny Chieng]

That's right. You stayed with your, with Bo Peters.

[Connor Mook]

You went, you stayed with Mook.

[Ronny Chieng]

Mook and I stayed. Which really.

[Chris Fleming]

Yes. Mook too.

[Ronny Chieng]

Well, we, he and I, last time we did Denver, we co headlined it Fun. And I stayed in the condo with the, with our feature at the time. It's his feature, but he asked me if he could borrow some toothpaste from me.

[Connor Mook]

Mook.

[Ronny Chieng]

Yeah.

[Connor Mook]

Mook Francis didn't like that. What do you think about that?

[Pete Holmes]

You know, usually I take the position of like, what's the big deal?

[Chris Fleming]

Yeah.

[Pete Holmes]

But in this case, your toothbrush is a very personal thing. And like jokes that involve like violating someone's toothbrush. I'm like, I don't find that funny. I don't like it because it's going in your mouth and we rinse it off. But it's mouth and toothpaste. If you're like me, it's going right on that brush.

[Connor Mook]

Correct.

[Pete Holmes]

So the rim. It's kind of like the toothbrush tosses the salad.

[Chris Fleming]

Yeah.

[Pete Holmes]

Of.

[Chris Fleming]

Yeah.

[Ronny Chieng]

I knew, I knew he wasn't going to take sterilized scissors and cut the toothpaste.

[Pete Holmes]

That's right. Needs to be rubbed off.

[Ronny Chieng]

I knew he was. There'd be contact. And if you saw this guy, you'd be like, like, absolutely not.

[Pete Holmes]

If somebody's asking, hey, can you spare some. Try some Aquafresh. I know, right? We might not.

[Chris Fleming]

There's not a way to put it on the, the bristles with. Just as a, with a hover.

[Pete Holmes]

You could twist it like honey. You know the dollop, those wooden things you dip in honey, like in the Honey Nut Cheerios commercial. You put the one of those in the toothpaste and you can drizzle it.

[Ronny Chieng]

But you have to think, is this Mook?

[Chris Fleming]

This is Mook.

[Pete Holmes]

I wasn't picturing a white guy. I'm going to be real. When you said Mook, I don't know why. I was like, this is a Kenyan, but here he is.

[Connor Mook]

Francis. Francis, what did you say when you asked?

[Pete Holmes]

You said, looks like someone actually photocopied you too many times.

[Ronny Chieng]

Yeah. I said, this isn't a bachelor party. Is that what I said?

[Pete Holmes]

Yeah.

[Ronny Chieng]

He goes, there was something else about it, though, that was weird. I'm forgetting.

[Connor Mook]

It was just funny that you guys had to interact all weekend. Like you guys went out to. You guys went to a diner.

[Ronny Chieng]

I took him to a diner. All this because Harry. Harry's friends lived in Denver at the time. Right. And Harry decided to crash on the couch. But that condo is very weird and zany and there's all kinds of funky stuff going on.

[Chris Fleming]

What about like a piece of like, tissue paper and you just grab a little bit of the toothpaste.

[Ronny Chieng]

If Connor Mook had considered any one of these types of sort of sterilizing

[Pete Holmes]

techniques, this guy's already brushing before he even realized there was an issue. Like, if you had said yes. Yeah, it would have happened. And then later you would have been like, did you just.

[Ronny Chieng]

I also saw what types of wrappers and things were on his bedside table and floor. So I knew what his mouth was full of and what he was cleaning.

[Pete Holmes]

He also has a mustache, which is the toothbrush of the face.

[Ronny Chieng]

This is not a guy.

[Pete Holmes]

Yeah.

[Ronny Chieng]

This is not a guy who has to make sure that, like, broccoli bits are out of his molars.

[Connor Mook]

It was a different time.

[Ronny Chieng]

It was like Burger King. At three in the morning, he eats

[Chris Fleming]

till the second he's asleep.

[Connor Mook]

This was Mook at his lowest. Not this picture specifically, but when at his lowest. When we were in Denver, what was

[Pete Holmes]

going on with Mook?

[Connor Mook]

He was just eating a lot of Burger King back then.

[Ronny Chieng]

Like I. We. There was a 711 right next to the club. And like, I. I have, you know, melatonin gummies before bed. And he has a slim gym.

[Connor Mook]

Yeah, yeah.

[Pete Holmes]

I don't want to huberman you, but melatonin is a hormone that your body makes. You shouldn't be supplementing it.

[Chris Fleming]

You think it's going to crush his

[Pete Holmes]

pineal glands, bro, it's going to calcify that. You might want to if you if you're interested in your melatonin, you should take calcium, which helps your brain make melatonin.

[Ronny Chieng]

That sounds cool. I'm open to anything. I'm a terrible sleeper.

[Pete Holmes]

Oh, really? Yeah.

[Chris Fleming]

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[Pete Holmes]

Yeah, well, L. Theanine.

[Connor Mook]

Of course.

[Ronny Chieng]

We're back.

[Pete Holmes]

Of course, Apogen, which is just chamomile and magnesium, but the one that has a P word, magnesium, phosphorus, or whatever

[Chris Fleming]

it is Huberman me up with. Or maybe it was the book the body by whoever the it was by. But they said that the. The pineal gland is so powerful that blind people can tell when the lights are on and off.

[Pete Holmes]

Oh, wow.

[Chris Fleming]

How nuts is that?

[Connor Mook]

Yeah, I could see that. I mean, if I close my eyes. But I guess that's not the same as being blind.

[Ronny Chieng]

Come to find that they've lost their sight, so their hearing is just so attuned they can hear the sort of gender been lying the whole time.

[Pete Holmes]

Well, that's good sound science. What are the factors? Yeah, can you feel the light?

[Connor Mook]

I mean, these ones, definitely.

[Pete Holmes]

You can feel hot. You see, you're good at comedy. You take a stand and say, it's hot. Sorry. I don't know why, but being with a younger comic is reminding me of all the things that I had to figure out. It's like, don't be like, I like cats. Don't get me wrong. Doctor.

[Chris Fleming]

Doctor being wishy washy.

[Pete Holmes]

I love cats. Like, we all. That's the job. Yeah, that's the job. Like, you know what I mean? Like, Bill Burr goes on and rants on something. Could Bill talk about the other side of it?

[Chris Fleming]

Yes.

[Pete Holmes]

Would that be fun? No, it's fun for him to be like, I hate fucking shopping carts. You know, whatever it is, clear perspective. Because I got Mooc on.

[Connor Mook]

Yeah, I know, right?

[Pete Holmes]

Like the guy following Bill to murder him. Get Mooc on the phone.

[Connor Mook]

Moocs going to love this.

[Pete Holmes]

Okay. I thought you were Kenyan. I knew a Kenyan named Mook. Mooc. That's real.

[Connor Mook]

That sounds more Kenyan.

[Pete Holmes]

Yeah. Add the second mooc. That's more of a African flavor.

[Chris Fleming]

I don't know why there's a battle rapper named Murder Mook, I think. And do the right thing. Of course.

[Pete Holmes]

That's what I'm saying. Mook is do the right thing. The character is his name. That's a Jeremy who goes by Mook.

[Connor Mook]

His name's Connor. His last name's not Mook, but he goes by Connor. Mook.

[Ronny Chieng]

I don't know why his last name's not Mook. No.

[Pete Holmes]

Now, wow.

[Chris Fleming]

He couldn't be Mo. His last name couldn't be Mook. He has red hair.

[Ronny Chieng]

Why did I. There's some back time. I don't know why this. I did not know that.

[Connor Mook]

Yeah.

[Chris Fleming]

Cuz I think that he had like another. He had like a accounting job when he first started working here, so he need to. He needed some type of pseudonym.

[Ronny Chieng]

Wow. Okay.

[Pete Holmes]

Is this your studio? Like, do these come down?

[Connor Mook]

No. So this is all of us. And then this on the other side is Roan's other show.

[Pete Holmes]

I've done that one.

[Connor Mook]

Hooping and hollering.

[Pete Holmes]

I don't know. I was gonna say.

[Connor Mook]

I was like. That came out like six months ago.

[Pete Holmes]

I don't think I did hooping and hollering. But whatever. I did have the same. You guys are reusing this sort of like sauna wood.

[Connor Mook]

Oh, yeah. You probably did KFC radio.

[Chris Fleming]

No, they just put this sauna wood in. How much do you think that this set costs? I got a text from my boss being like, this set cost X amount of amount Better be worth it.

[Connor Mook]

Yeah. How much with.

[Pete Holmes]

Including the furniture?

[Connor Mook]

Yes, everything.

[Pete Holmes]

It's like, prices, right? This set cost $32,000.

[Chris Fleming]

It cost $55,000.

[Pete Holmes]

I know a guy could. Camera that doesn't make a shutter sound

[Chris Fleming]

and could have gotten $17,000 off.

[Ronny Chieng]

Do you think that includes those lights, though?

[Chris Fleming]

No. The tech team said they added nothing. It's just the fabrication of this. I took a picture. I was like, where's this? Where's the $55,000? $10,000 to take down the old set? The bookshelf?

[Pete Holmes]

I. I had a guy that could have done that for $4.

[Chris Fleming]

Yeah.

[Pete Holmes]

What?

[Chris Fleming]

I was getting my balls broken.

[Pete Holmes]

Weird, man. It used to, like. I. Because I've been doing mine for. I don't even know. It's over a decade. It used to be like ham radio, you know, it was like Mark Maron in his basement being like my cat on my mouth. I don't know why I said that, and I don't know why I said it. Like Jack Nicholson for. For some reason. But it was very low fi. Yeah. And like, Marin's point, like, when he started wtf, which obviously inspired my show, that his managers, like, laughed at him. They were like, why are you wasting your time? And I remember that. I'm old enough to remember, like, podcasts were like. It was like a joke. Yeah. It was like the Microsoft Zune. It's like, oh, you do a podcast. Can I get that on my zone? Like, it was like that. And now you're Here we're sitting in

[Chris Fleming]

a double studio, like, with eight overhead directional lights.

[Pete Holmes]

Exactly. In, like, a tech office. Like, I've been in the Facebook office. Like, this isn't that far off.

[Chris Fleming]

It's insane.

[Pete Holmes]

There's not a cereal bar.

[Connor Mook]

No. Like you, if you were here a couple years ago.

[Pete Holmes]

Really?

[Connor Mook]

Cereal everywhere.

[Pete Holmes]

Every like. Which is funny. That's not expensive.

[Ronny Chieng]

I'm a little mad in Chicago now, but.

[Connor Mook]

Yeah.

[Pete Holmes]

This is what happens when. When money finds something is people start charging $50,000 to put up something that. If we were doing this. And I'm not making fun of your. Whoever did this, but, like, when you were starting, you would have found a way to do this exact set for $800.

[Chris Fleming]

Yeah.

[Ronny Chieng]

And if by money finding something, you mean ice finding all of the unskilled laborers in New York City. Yes. That is why we had a team of like. Like, Etsy handlers come in and assemble this instead of a family from Venezuela.

[Pete Holmes]

Yeah, exactly. This has Etsy vibes, which, like.

[Chris Fleming]

Or it just. It rankled me a little bit. It ruffled my feathers that my boss is on my ass about this. About the. The set. As if I demanded Noah's Arkwood.

[Pete Holmes]

Is this your set?

[Chris Fleming]

Yeah, for the basketball show. Better be good. It's like, dude, I didn't ask for it. I could have. Would have taken a wood composite faucet.

[Connor Mook]

You like ball? You a sports guy?

[Pete Holmes]

No. No, not a 6.

[Connor Mook]

6. 6. 6.

[Pete Holmes]

Barely touch the room, really.

[Chris Fleming]

But you can touch the room.

[Pete Holmes]

But I can.

[Connor Mook]

Yeah. I mean, that's all that matters.

[Pete Holmes]

I mean, I can touch the room without really jumping. I just get my arm up there. It's a. It's a shame that I can't dunk. I. I'm the same height as Michael Jordan or I. They lie in the stats a lot, though.

[Chris Fleming]

Yeah. He's six. Six. I think he's legitimate.

[Pete Holmes]

Before lying was invented, he's six one.

[Chris Fleming]

Yeah.

[Pete Holmes]

Is that real?

[Connor Mook]

It's all lies. Hell, no. No. He's probably 6 5.

[Pete Holmes]

They reboot the last dance just to have this cut to him with his dead eyes being like, I am smoking drunk. We need to take a break. He cries because of what you said.

[Chris Fleming]

Yeah.

[Pete Holmes]

Walks off that house. Doesn't look fun. Where he lives, he lives in, like, Superman's Fortress of Solitude.

[Chris Fleming]

Yeah, they've been trying to sell it, too, for, like, a while. His Chicago mansion with, like, the 23 on the gates, and nobody wants it. Shocking, right?

[Pete Holmes]

Oh, you think MC Hammer would have swooped in and just taken that? Like, remember well, there was a hater Hammer palace that they couldn't. I remember.

[Chris Fleming]

Of course.

[Pete Holmes]

Yeah, I would buy it.

[Connor Mook]

I mean, the 23 on the front, you got to be a big MJ fan if that's going to be Jim Carrey.

[Pete Holmes]

Off, off brand Jim Carrey fan. He had that movie.

[Ronny Chieng]

I. I just played Michael Jordan's golf course in Florida. It's called Grove 23.

[Connor Mook]

Oh yeah.

[Ronny Chieng]

And you come in and I can give this to our beloved editors. But I'll show you guys so that. And then this will be on the screen. But you drive in and. And you see the gift gate and the ins like insignia of the 23. I mean it's all done in Roman numerals. It's pretty cool. Just bear with me for one second. Here we go. Oh, yeah. Here it comes, guys. You'll see in. In just a second. I don't know why I'm showing you this. It's not really. Oh, no.

[Pete Holmes]

Oh, no.

[Chris Fleming]

We'll start from the beginning.

[Ronny Chieng]

No, no, no, no, no. Here, look, look. You'll see. I mean it's everywhere. This one is.

[Pete Holmes]

Camera sideways next time.

[Ronny Chieng]

You see that?

[Pete Holmes]

No. What did it say?

[Ronny Chieng]

You couldn't see it?

[Connor Mook]

No, no.

[Pete Holmes]

I can't see anything.

[Chris Fleming]

Holy.

[Ronny Chieng]

It says XX. Xx. And then three ones, Roman numerals. And that. That is everywhere. That 23.

[Connor Mook]

That's pretty cool.

[Ronny Chieng]

Is just like the whole prevailing.

[Connor Mook]

You go to the pros drop.

[Ronny Chieng]

Yeah, I did.

[Connor Mook]

Any good gear?

[Ronny Chieng]

There was some cool gear. They make some cool like stuff that you can only get there, which is cool. I had a friend who asked me to pick him up some stuff. The other cool thing about it is that because Michael Jordan loves cigars, you can smoke cigars in the main restaurant, like indoors.

[Connor Mook]

That's fun.

[Ronny Chieng]

And then they have a. I think they have some kind of.

[Pete Holmes]

It.

[Ronny Chieng]

It felt like they had a filtration system that makes it still tolerable to those who don't want to just be inhaling.

[Connor Mook]

Yeah, probably.

[Ronny Chieng]

And then they had all the doors open and then the air condition. That's what. You know.

[Chris Fleming]

That's so rich.

[Ronny Chieng]

You have money to really burn.

[Chris Fleming]

Yeah.

[Ronny Chieng]

All the doors open on a humid floor today with the air conditioning just.

[Connor Mook]

Yeah. Just going outside.

[Ronny Chieng]

Fighting a losing battle. Dissipating endlessly into the humidity.

[Pete Holmes]

Yeah, yeah.

[Ronny Chieng]

But it was cool. Yeah. And he's always there.

[Connor Mook]

Did you. Was he there?

[Ronny Chieng]

I didn't see him.

[Connor Mook]

You think he was there? Could you feel it?

[Chris Fleming]

Was he like Phantom of the Owl?

[Ronny Chieng]

No, he's pretty. He's pretty Noticed. I'm sorry, Ron. He's pretty noticeable. Like, he takes a group of six and everyone gets their own cart. And he's famous for, like, he'll. He'll gamble with any member and he's very, like, approachable about it. So if this kid I was playing with, it was like 23. He was like, yeah. If I went up to MJ right now in the restaurant and I was like, closest to the pin off of 18 near the green for 500 bucks, he would immediately be like, yep, let's go.

[Connor Mook]

Yeah.

[Ronny Chieng]

And. And his whole rule is, like, he'll gamble for anything as long as it makes you uncomfortable.

[Connor Mook]

Yeah.

[Ronny Chieng]

So he doesn't care if we're betting 500,000 or 50 bucks, so long as it is an amount of money that if you lost it. Did I already say this?

[Connor Mook]

Yes.

[Pete Holmes]

Not to me, but.

[Connor Mook]

Not to me. This is brand new for me.

[Ronny Chieng]

This was pre mind.

[Connor Mook]

This was pre mj.

[Ronny Chieng]

Did I tell all those stories that I just told?

[Connor Mook]

No, no, no.

[Pete Holmes]

This is.

[Ronny Chieng]

There was some new information.

[Chris Fleming]

Yeah. You're going to win yourself.

[Ronny Chieng]

All right. Thank God.

[Pete Holmes]

At a certain point, I think past the 10 year mark, I was just like, I'll just assume I've said everything.

[Ronny Chieng]

Yeah.

[Pete Holmes]

But if I'm Saying it again, 10. I've heard it before. I'm. Were you interested in what you were saying? Did you. Was there still some juice in it?

[Ronny Chieng]

I was interested, yeah.

[Connor Mook]

Excited about Roman numerals.

[Pete Holmes]

I mean, like. Yeah. The ac. You loved it. Gambling.

[Ronny Chieng]

If I didn't offer any new information, I would be concerned.

[Connor Mook]

No, no, There was new information for what?

[Chris Fleming]

For the fans, audience or for your own?

[Ronny Chieng]

For my friends. For my mind.

[Chris Fleming]

But like, with your buddies, like, isn't it fun to, like, tell the same old stories? Like, oh, yeah.

[Connor Mook]

It's all it is.

[Chris Fleming]

Yeah. At a certain point, you.

[Pete Holmes]

That's what a friend is. Yeah. A friend is someone who will tolerate the insanity of your repetitive mind.

[Connor Mook]

Yeah.

[Pete Holmes]

And not judge it because, I mean, that's what we're all burdened with. Yeah. Like, I. Like, you ever watch a movie you've seen before and you realize you're having the same thoughts as you had it the first. Because you see certain things and it makes you think about certain things and you're like, this is a repeat. Like, I've seen this before and I've seen this before. That's what we are.

[Ronny Chieng]

We're just like.

[Pete Holmes]

Like, it's not a bad thing. It's just like, you need. It's nice to recognize that your Thoughts aren't really that personal.

[Ronny Chieng]

I. I rewatched Inception this weekend. I've probably seen it 10 times, and I hadn't seen it in years. And what I realized this time is that I still do not understand the movie. Like, after all, I thought I had it figured.

[Connor Mook]

Yeah.

[Ronny Chieng]

Like, the last time I saw it, and this time I was like, oh, no. There's a lot of pieces of this from the. The kick, like, the falling, the gravity stuff, all of that, the time distortion, why someone can die, and then you go deeper into a level and you can rescue them from there. It was above my head.

[Connor Mook]

Yeah, that movie's pretty confusing.

[Chris Fleming]

Tenet was just, like, the more obtuse version of that movie.

[Connor Mook]

I've never seen that one.

[Pete Holmes]

Tenet is upsettingly bad to me.

[Chris Fleming]

Yeah, no, it's bad.

[Ronny Chieng]

It's too confusing.

[Pete Holmes]

I don't like it. It's a touching. I love Nolan, and I've watched. You know what's weird about me, I guess, is, like, I don't like Tenant, but I will watch YouTube's talking about tenant or Christopher Nolan talking about Tenet. I like that. But I don't just want to be a mouse in the maze trying to figure. And that. That might be my age when I

[Chris Fleming]

want to be on top of the maze and just being like. See someone go through it, be like, oh, that's how you get out.

[Pete Holmes]

Yeah. That's an interesting thing. It's so much better than you think it is. Like, I watch movie. YouTube's about how the prestige isn't about what you think it's about. And I'm like, I don't know why, but I love, like, deep analysis, but I don't want to be burdened with having to do the deep analysis.

[Ronny Chieng]

Yeah.

[Pete Holmes]

I also just. I didn't really.

[Chris Fleming]

You want to. I mean, to make art that people is. People aren't supposed to get is not good art. I don't think.

[Connor Mook]

Like, did you see, like.

[Pete Holmes]

I didn't see Weapons.

[Connor Mook]

Like, Weapons was like. It's like. It's like a 24 horror movie.

[Pete Holmes]

Yeah. Zach Kreger wrote it. He's a buddy of mine. But I haven't seen.

[Connor Mook]

Yeah, great movie.

[Pete Holmes]

I love Kids Go Running.

[Connor Mook]

Yeah. Yeah, I watched. I saw it in theaters. I loved it.

[Pete Holmes]

Yeah.

[Connor Mook]

And, like, I had an idea of what it was about in my head, and then I went home and I Googled it, and it was like, not even close.

[Pete Holmes]

Oh, interesting.

[Chris Fleming]

Yeah.

[Pete Holmes]

Yeah. I guess that's part of it. And we are such a rewatch culture. Like, the first time I saw the Matrix, I realized, like, I was probably your age, and I was like, I loved it and had no idea what it was about. And then I watched it again. I was like, oh. And, like, you realize, like, they were explaining it the whole time. You were just like, look at Keanu. Like, you just did.

[Chris Fleming]

Yeah.

[Pete Holmes]

Care. So sometimes it takes a while to understand.

[Connor Mook]

Yeah. Yeah.

[Chris Fleming]

A couple of years ago, my relatives came into New York, and I really wanted to take them to see some comedy. And we went to the Cellar, and we waited in line at the Cellar, and we didn't get tickets. And so instead of going to a show, we just. I just showed them crashing, and I was like, this is it. Basically, like, a decent idea of.

[Pete Holmes]

And also, the humiliation of not getting into the club primed them for the show.

[Chris Fleming]

Yes, it feels like it because to

[Pete Holmes]

your point, it's more interesting, like, the seller to me. I'm not saying I don't still sort of revere it as a space, but, like, I used to stand. That's really where I barked. On that corner, West 3rd and McDougal. So I could see the Cellar, and I'd be handing out flyers for another club, and I'd watch. You said Dove Davidoff. I saw Dove Davidoff in his, like, comedian leather jacket. It was very popular at the time. He was crossing the street, and he just went in like it was his living room. And I literally. I'm handing out flyers, people are taking them, throwing them away right in front of me, and I'm like. I look at Dove, and I just go, someday. I really did this. I said, someday out loud. And what I didn't. I'd like to think I had some appreciation for the struggle and the climb. I. I was that guy that used to say, they're gonna write books about this, like, at an open mic in Chicago. So three years in, I'd be like, they're gonna write books about this. This. My friend Mike Bridenstine just wrote a book about that comedy scene. So it was true. Yeah, like, they did write books about it, but, like, so I did appreciate it. I wasn't postponing at all, but, like, looking back again just to that point, like, that sort of was the juiciest. I prefer this a million times, but that was the most interesting time of my life. To look at something and go, someday. Like, there's very little in my life that I look at and go, someday. You know what I mean? Like, a cruising altitude is way less interesting than, in a sense.

[Chris Fleming]

Yeah, yeah, yeah.

[Ronny Chieng]

Makes sense. I did the Thursday Mike at the Grizzly pair for like, three years. And you'd take the West 4th subway station, get out. You walk past the cage and then turn right and you'd go past the Cellar, I think. Or maybe it was before it, but you'd see it. And I would always peek at the board with the handwritten names and all the credits.

[Pete Holmes]

Yeah.

[Ronny Chieng]

And I had that. I mean, it's eerie. I had the exact same. To the degree. Someday when I got past like three or four years ago now. And I got in and she came up and we walked up and she asked me for the headshot of Ales and I and all bio and all that. And then I was just holding it together and I walked out, turned right where they, like, back the lineup and then down that left side street and just openly wept.

[Pete Holmes]

Wow. Minetta. That's where we took the poster photo of crashing. That's where we put the couch on Manetta Lane.

[Chris Fleming]

Right.

[Ronny Chieng]

It meant more to me than in anything.

[Pete Holmes]

Yeah. Yeah. I didn't mean to take away from your story by telling you an asinine thing about. But that is beautiful. Yeah.

[Ronny Chieng]

You see the summit for so many years, but you are hiking a smaller mountain.

[Pete Holmes]

Yeah. That. You know, there's a lot of stories about things not being what you thought they would be. And I have lots of stories like that. But doing the Cellar for the first time didn't disappoint. But that's what they. That's what human beings do, is we imbue things with meaning. And the more year. It's like a battery. The more you charge a place or a thing with meaning and then you do it. The thing you get passed or whatever it is. All of that stuff that you actually put into it, you find what you put into it is still there. Like, does that make sense? Like, you filled the toy box and then you open it, you're like, look at all these toys. That was your heart that you were finding when you did it. Like, the places. It's just a place, but it's fun. What I realized from doing comedy is, like, community and a culture and a thing. All of that belonging is super important to human beings and being with other comics and coming up with them and reuniting with them and all that. That's. So many people don't have culture. Like a culture, and we really have a culture. I think that's one of the most exciting things about it. So you have that story, and it's also my story. That's why When I meet a comic, I'm just like, I know we've met before, but I, but I'm like, I know we have more in common because we were raised on the same mythology. You know what I mean?

[Chris Fleming]

See, Sass just takes it as a foregone conclusion. Like he doesn't even aspire to it. He's like, this shit's fucking boring. Yeah, I'll be here someday.

[Pete Holmes]

No, it is interesting because the more you suffer, the more you pull that bowstring back, right, the more likely you are to stick with it. And I couldn't know. But what'll be interesting is will it hold your attention? And it's fine if it doesn't. But like the guys, like I can't include you because I don't know. But the guys like me that really were grinding for 10 years. You play cards. It's like being pot committed.

[Chris Fleming]

Yeah.

[Pete Holmes]

I put so much into this, I'm not going to leave. And now I'm, I'm a comedian. I'm a real comedian. I'm not going to walk away. But it's because of that investment up top that you're not going to walk away. And I'm not saying you waltzed in with no effort, but like if you do pop off really quickly like Machine Gun Kelly, right? He's like, now I'm gonna do pop punk. And I'm like, yeah, because you broke when you were like 24.

[Ronny Chieng]

No wonder you're bored.

[Pete Holmes]

You know what I'm saying? Trying to use hip hop references.

[Chris Fleming]

Now I understand because I was lost for a while. Machine Gun Kelly, did I get it? A white rapper.

[Pete Holmes]

I only know the white ones. Mgk, Eminem.

[Chris Fleming]

Yep. And that's both of them.

[Pete Holmes]

You're forgetting the Ojima man.

[Chris Fleming]

Vanilla. What do you guys, what's your guys thoughts on meeting you're here Heroes. Because it's a similar thing, but often has a antithetical experience.

[Ronny Chieng]

I think it can go either way more often than not. At least when I've met people I really look up to, they've been nice. I haven't quite yet had the really disappointing eye opening. Holy shit, I had that guy pegged all wrong.

[Connor Mook]

Yeah, I think you got to really put yourself out there for that to even happen though, right? For the guy to be like, fuck off.

[Pete Holmes]

Right.

[Connor Mook]

You gotta be saying something like maybe.

[Ronny Chieng]

I mean, you hear those stories about, you know, usually it's like a waiter at a restaurant who serves some celebrity and they're like, sorry, this omelette was a disaster.

[Connor Mook]

Yeah, yeah.

[Ronny Chieng]

Or they don't tip well or whatever. I think that's.

[Connor Mook]

Yeah, that's true.

[Pete Holmes]

Well, once you're super famous, everything you do is a story. And I'm not letting them off the hook for being turds. I'm just saying. Saying, like, one time when I was coming up, we perform at the ecb, and we'd go to this bar across the street, and Alec Baldwin was there because he used to be there for, like, 30 rock reasons. I don't know.

[Chris Fleming]

Yeah.

[Pete Holmes]

And he bought our table, like, chicken wings. And that was a story I told for 10 years.

[Chris Fleming]

Why did he. Why did he do that?

[Ronny Chieng]

Well, he shot one of them, so

[Chris Fleming]

it was an apology wing.

[Ronny Chieng]

Apologetic wings. Yeah.

[Pete Holmes]

But it, like, worst of the group. The burden of being super famous, where if I can't. I didn't even see it coming. But, yeah, I sympathize. When I was doing Crashing, I went to the Cellar, and there was an SUV parked idling out front. Kind of your MJ AC moment. And I'm going in the club, and that's. Chappelle came out and he was like, hey. Hey, man. Dune, Radio City. I'll come do Radio City. He doesn't talk like that anymore. No, that's cool.

[Connor Mook]

That's pretty.

[Pete Holmes]

That's killing him. Softly Ch. Hey, man.

[Ronny Chieng]

Yeah?

[Pete Holmes]

You got to come do it. I can't do it. That. No, that sounded like a white guy doing pretty good. Hey, man. Hey, man. Hey, man. Hey, man. Hey, Pete. You got to come do it. You can kind of hear it.

[Chris Fleming]

Yeah, I thought the first one. Was it like that.

[Pete Holmes]

Yeah, yeah, yeah, that was. That's killing him. Softly.

[Chris Fleming]

No, no, no. I'm saying the first. Like that lower tone, the cigarette voice.

[Pete Holmes]

Yeah. Hey, man.

[Chris Fleming]

Yeah, that was nice.

[Pete Holmes]

Yeah. So he asked me to. He was like, we're doing these shows at Radio City. Come do it with me. And I was filming Crashing at the time, and I wasn't doing standup. I was doing fake standup, which was surprisingly, like, real standup, but, you know. But they're background actors, but you're still kind of doing it. But, like, I didn't. I really didn't want to do it, like, because I wasn't strong. I wasn't, like, doing sets, and I was filming a show 12 hours a day. I'm so happy that he asked me, and I was so honored that he asked me. So, of course I said yes. I didn't even think about it. I was like, yes. And then I did some sets at the Cellar to warm up. I'm like, recording. I'm only doing, like, seven minutes or something. And, like, I got to Radio City. I'm sure all of you have done this in my mind. I'm gonna get to Radio City, and somebody's gonna spot me and go, Mr. Holmes, this way. Take me down some alleyway, open some doors. It's all purple lights, big cushy chairs, snacks and drinks. And there's Chappelle, of course, and Kevin Hart is there. Everybody's there. It's a scene. We're all hanging out. It was the saddest, loneliest experience of my life. Not really, but I got there. The first thing I did, I walked in with the crowd. I get in, and there's, like, attitude, like pages. Like people that work at Radio City. And none of them are happy. They're all like, oh, this fucking crowd. I go, hi. I'm on the show. I'm waiting for someone to be like, my goodness. And they're like, you go. You still got to go through the detector. It was like, all right. I go through. They take my phone, they put it in one of those pouches.

[Ronny Chieng]

Oh, no, the underbag.

[Pete Holmes]

And I go on the show, they go, I don't care about.

[Ronny Chieng]

That's what everyone says.

[Pete Holmes]

They're yelling, I don't care. And they put me in an elevator. I go up to my. Where my green room is. Remember what I'm picking.

[Chris Fleming]

Yeah.

[Pete Holmes]

Hey, man. Now it's young Chappelle. What's going on? And it's an empty dressing room, like Rockette style. Like, the bulbs, some of them are out. There's nothing in this room. There's not even water. There's nothing. I'm sitting in this long room designed for. For the Rockettes, by myself with my phone in a bag like a fucking dipshit. I go, well, I'm sure there's, like, water in the fridge. I open the fridge. This fridge hasn't been on for years.

[Chris Fleming]

Stop.

[Pete Holmes]

You know that smell? It just smells like an off fridge. I close it, and I just sit there. And I realize I'm nervous. Cause I haven't been performing, and my set is on my phone.

[Ronny Chieng]

Yeah.

[Pete Holmes]

Looking back, I would have cut open the bag. Fuck you. All of this. And I'm going last. I'm. You know what I mean? That would be a good story. I didn't. You know, when you're like, confidence is shook. You don't think of solutions. You don't think, like, I can cut this open. Nobody's gonna know or care.

[Chris Fleming]

Yeah, you spiral.

[Connor Mook]

Yeah.

[Pete Holmes]

I Spiral. Yeah, I'm catastrophe. I'm like, I can't even get my set. I went down and. And that's where everybody. I went downstairs before the show. That's where everybody was. But I went. And it was, like, not super fun. Lauryn Hill was there, though. Lauryn Hill saw me do okay,

[Chris Fleming]

but

[Pete Holmes]

Chappelle was very nice. None of that is on Chappelle. But afterwards, I went up into his dressing room. Nobody said anything about my set. Nobody's thinking about you. Nobody's like, I did fine. I did well. That's not really the story. In fact, when you're performing at Radio City, what I learned. I forgot what my opening joke was, but I'm sure I had something fast. I said it and I'm like, oh, it didn't work. And then this, like, tidal wave of laughter hits you, like, three seconds later. So you realize you have to, like, wait. There's like a delay. There's a lag in that many people. Like, you know when a truck goes by you and then you feel the wind. Yeah, it was like that. It was not.

[Connor Mook]

That's crazy.

[Pete Holmes]

It was not chill.

[Connor Mook]

I mean, that's a. That's a pretty. How many people does that room sit? Like, 6,000.

[Ronny Chieng]

6,000.

[Chris Fleming]

Damn.

[Connor Mook]

That's crazy.

[Pete Holmes]

It was crazy.

[Connor Mook]

Walking in with the audience is hilarious.

[Pete Holmes]

Yeah. And then being really rude. No one said, welcome. No one said, there are people in

[Chris Fleming]

the audience being like, Pete.

[Pete Holmes]

No. And it's interesting. I think crashing must have made me a lot more recognizable because at that time, I could still just walk into radio city with 7,000 comedy fans. No one said, shit. People were like, get in the fucking metal detector. And I was like, sorry, sorry. Sorry.

[Chris Fleming]

Was a lot of the crashing stuff pretty analogous to stuff that had happened to you or. Or was like. Like one of the storylines. Like, somebody, like, shaves before a show.

[Pete Holmes]

Oh, yeah.

[Chris Fleming]

Shaved his faces. That and at all based off that

[Pete Holmes]

had to be somebody. It's funny that you picked. That's the one of two episodes I didn't write. So out of that.

[Chris Fleming]

It sucked. I thought. Yeah.

[Pete Holmes]

It was missing a certain. Yeah, no. Judah Miller, who is our showru. Or wrote that one. And obviously I was involved. But there were 24 episodes and I wrote 22 of them. And, you know, other people were involved, but I always liked to do the first pass. And usually everything would have some sort of corollary. But that one might have been somebody else's story. Like. Or. It's just kind of general. What is it? No big moves on Game day. Like, don't change the routine. The morning of the race, we just wanted to kind of talk about that. But almost everything in there is something, something. And a lot of the good advice that I got, like, Marina Franklin says to me something that somebody said to me. I forget who. It'll come to me. But she said, if it sucks, that's how you know you're doing it, right? And that was such a. That's what crashing is about is like, it's not, oh, this sucks. I must suck. It's like, no, actually, it's what we were saying earlier. It sucks for everybody. And this is, like, kind of a beautiful rite of passage to Buck Bomb at the village lantern. Like, you know who's bombed at the village lantern? Fucking everybody. Like, welcome. Like, take your stripes. You know what I mean? Like, being folded in and just, like, you know, I don't think it's a stretch to say, like, just, like, male initiation. All these things, they're always kind of painful. There's always something. There's some sacrifice. I think doing an awful road gig is. I'm not into branding, but it's like your way of being branded as a comic again. It's why I feel kinship to comedians. I' know you know what a comedy condo is. Like, I've also had a guy named Mook ask me for toothpaste. Like, that. That does bind you together.

[Ronny Chieng]

Why, if you don't mind me asking this, why did. Were you guys trying to have a fourth season of crashing?

[Pete Holmes]

Oh, no, I don't mind that at all. We were. It's funny. It's hard to know if. If it's. If you're, like, changing the memory to make yourself into a psychic, but there. I think people on the staff would agree that there was a feeling that we weren't gonna get a fourth season while we were making the third season.

[Ronny Chieng]

Oh, okay.

[Pete Holmes]

And when we shot the last shot, right by the papaya dog, where I'm walking with Jamie, or Ali is her character's name, but it's Jamie Lee. She and I are walking. We shot two versions of it. One where we kiss and one where we don't kiss. And we knew that the kiss version would be if we're canceled and we were canceled and we do the kiss version. Cause that's. That's like. That's a series arc. It's like, oh, okay. Like. And I'm really proud of that. Like, I'm worried. This sounds disingenuous, but if we had done a fourth season. Cause we Broke it. We were starting to outline it. Pete would have gotten a talk show. That's what happened to me next. And then it's not crashing anymore. It's flourishing.

[Ronny Chieng]

Yeah, right.

[Pete Holmes]

It's supposed to be about a guy whose only dream was to be folded into the New York comedy scene. And it ends, and he's folded into the New York comedy scene. He's passed at the side. I don't know if he's passed. I can't even remember.

[Ronny Chieng]

Yeah, you got passed.

[Pete Holmes]

I got passed.

[Ronny Chieng]

You were with Jabouki on that and talking to Esti.

[Pete Holmes]

Right, okay.

[Ronny Chieng]

Yeah.

[Connor Mook]

Oh, yeah. Jabouki's in that. I forgot.

[Pete Holmes]

Yeah. Jabouki White. And she passes me. So Pete, my character, Pete is now going to do comedy, and that's all he wanted to do. And the girlfriend. And this is sort of telling about something I had to figure out as a person, too. Jamie. Jamie's character was just kind of. She represented, like, comedy. Like, just my life. Like, I'm happy with her because I'm happy that I'm in comedy. Like, I don't think Pete and Jeff. Jamie. Stay together. Or Ally. I keep calling her Jamie, but you know what I mean.

[Chris Fleming]

Yeah, yeah, yeah.

[Ronny Chieng]

I had a huge crush on her from that show.

[Pete Holmes]

Oh, she's great. Yeah, she's so fabulous. We're dear friends, and we. We dated for a year. In real life, we were friends.

[Ronny Chieng]

I didn't really like her that much. I would. I, like, I respect her. There's.

[Connor Mook]

I'm friendly woman.

[Ronny Chieng]

I'm so glad that a friend of mine dated her. And because of that, that I only see her in platonic terms.

[Chris Fleming]

And you've always said that.

[Pete Holmes]

Yeah. Love her. We don't think of each other in that way. It's very. Jerry. Elaine.

[Connor Mook]

Yeah.

[Pete Holmes]

Like, we dated a little bit, but, like, we've been friends for 10. Over 10 times that.

[Ronny Chieng]

Yeah.

[Pete Holmes]

So it really is, like, something I never thought I would have, but, like, a true close girlfriend. Friend who was a girlfriend.

[Ronny Chieng]

Yeah.

[Chris Fleming]

Yeah.

[Pete Holmes]

I mean, very brief.

[Chris Fleming]

One of the things I subconsciously stole from the show is when I'll see someone doing a joke and I'll just be like, so good. So good.

[Pete Holmes]

Yeah. So good episode. And Jamie, you know, I should step that out a little bit. She was writing on the show and she auditioned. I think when we were promoting it, Jamie was kind of like, maybe don't mention we dated. So I do want to step that out and be like, she got it on her own accord. There was no, like, word I put in. She Auditioned and Judd was blown away. And I think it was probably picking up on this chemistry that we had as friends, but she earned it, and she was fabulous.

[Ronny Chieng]

Do you want us to cut that whole thing, starting with me saying that I have a crush on her? We can do that. We can go bring a clap.

[Pete Holmes]

You kidding?

[Ronny Chieng]

Back in here. We'll cut that whole part.

[Pete Holmes]

I think Jamie, you'd be dumb to not have a crush on Jamie. She's so funny and wonderful.

[Ronny Chieng]

She went on to write for Ted Lasso, right?

[Pete Holmes]

Yep.

[Chris Fleming]

Yeah.

[Pete Holmes]

And I believe.

[Chris Fleming]

Oh, you really got a crush on her.

[Ronny Chieng]

Well, I was just impressed. And then I. And then I did a show that she was on very shortly after that where I was like, whoa, I thought you were doing better than this. And then I saw that she was. She was on Dead Lasso.

[Connor Mook]

I, I. She was on the My. When I filmed a don't tell set, like, two years ago ago in San Diego. And I was watching Crashing and she was on the show.

[Pete Holmes]

Oh, wow.

[Connor Mook]

And I was like, what the.

[Pete Holmes]

That's crazy. That's crazy. Yeah. Yeah. The building, the. The fake Boston exterior. Because the Boston's gone.

[Ronny Chieng]

Yeah. But it was Greenwich Comedy Club, right? Or did you film it?

[Pete Holmes]

The exterior. The. The interior was a set.

[Ronny Chieng]

Oh.

[Pete Holmes]

Which is insane.

[Ronny Chieng]

Wow.

[Pete Holmes]

And the exterior was like a frozen yogurt shop or something.

[Ronny Chieng]

Is the Boston what Greenwich Comedy Club is now? It's, like, three doors down from the

[Pete Holmes]

cellar, next to the fire station. Yeah, I don't know. I would imagine so.

[Ronny Chieng]

Okay.

[Pete Holmes]

It's.

[Connor Mook]

Isn't that on the Strip? Or is that.

[Ronny Chieng]

No, the strips on the Upper east side.

[Pete Holmes]

This is west third, right by the.

[Connor Mook]

Isn't there, like, 10 clubs on that street?

[Pete Holmes]

Yes, and there's going to be more of that McDonald's just.

[Ronny Chieng]

Yeah, but the Village Lantern just got shut down.

[Pete Holmes]

Oh, really?

[Ronny Chieng]

Yeah.

[Pete Holmes]

That's a bummer. Are we running out of time?

[Chris Fleming]

Yeah, you guys are.

[Ronny Chieng]

Yeah.

[Chris Fleming]

You're. You're.

[Pete Holmes]

I'm having a great time. I'm just aware that we have another thing, and I see you squirming.

[Ronny Chieng]

Are you going to do a set on Colbert?

[Pete Holmes]

No.

[Ronny Chieng]

You'll just guest.

[Pete Holmes]

Yes. But what's great about that is you. You just do. You know, usually on a pre interview, a producer will, like, ask you about your life and be like, oh, you have a daughter, whatever. But when we do Colbert, you just go like, I want to do this bit and this bit and this bit and this bit. And you do plan it like a set. Oh, that's nice. And. But Then he's there. It's so fun. It's so fun.

[Chris Fleming]

Set you up.

[Pete Holmes]

He sets you up. And. And there's a clip of me where sometimes he doesn't help, like, in a funny way.

[Connor Mook]

Leaves you out to draw.

[Pete Holmes]

I had a joke. Yeah, I had a joke about how, like, we all have group mode and we have solo mode, and, like, some. I. I was really recently with somebody, and I watched them transition from group mode to solo mode, and he was like, but if you were there, how could they have been alone? And I just yelled at him for five minutes for ruining it. Like, you're supposed to help me. But that. That's funny, too. Like, I don't. I don't care.

[Chris Fleming]

Like, yeah.

[Pete Holmes]

If the bits don't come out or if one of the. You know, you really run a risk with somebody as fast and funny as Stephen, that he's going to know where the joke is going. And he very well may say the punchline before you get. Get there. So you just have to. It's an exercise in fluidity. You just go like, that's exactly right. You have to be like, I'm glad you got that first. And let's. Let's go into it. You have to. So there is something conversational to it.

[Ronny Chieng]

But, I mean, Letterman would never.

[Pete Holmes]

But I don't think Letterman was trying. He was just planning his dinners. I love Letterman, but I know what you mean. He wasn't really, like, chomping at.

[Ronny Chieng]

No, he wouldn't cuck your punchline from

[Pete Holmes]

you because he was more of a laugh, I think.

[Ronny Chieng]

Yeah.

[Pete Holmes]

Colbert is definitely. I don't know. I think it might go down as one of the great honors of my career to be in these last 10 weeks of shows, because it's really. He's having people on. It's a dumb flex. No, no, it's cool that he likes.

[Ronny Chieng]

Yeah, yeah, it's cool.

[Pete Holmes]

And I'm just take. I'm having a moment of gratitude to be like, that's.

[Connor Mook]

Yeah, it's like when Norm did Letterman's last episode.

[Pete Holmes]

Just who do you want to mess around with?

[Connor Mook]

Exactly?

[Pete Holmes]

And Conan. You know, Conan and I did a talk show together. Conan used to call Martin short a day off. And that's the compliment.

[Ronny Chieng]

I'm always going, oh, that's cool.

[Pete Holmes]

I want the host to say that was a day off, because usually they have to pull it out. But you just go, like, he says, how are you? And you just go, yeah, yeah.

[Ronny Chieng]

Well, I think I can absolutely say that the three of us have had a day off today.

[Pete Holmes]

Oh, that's really nice of you. It's funny that you said that, because I'm like, that's what I'm trying to do for you. Like when people come on my podcast and you say, how are you? And they tell you, you know, they don't just go, like, I'm good. Like, they go, like, that's great. You know, whatever. And you lead them somewhere, or you. They lead you somewhere. That's a day off. Yeah.

[Chris Fleming]

Hell yes. You're the man. Thank you so much, bro.

[Ronny Chieng]

Thanks for having me. What are we looking for?

[Pete Holmes]

The Special is on March 24th. It's called silly, Silly Fun Boy. It's on a website called YouTube.

[Connor Mook]

Hell, yeah. Yeah.

[Pete Holmes]

YouTube.com I believe.

[Chris Fleming]

Run that thing up. Hell yeah.

[Pete Holmes]

Awesome.

[Connor Mook]

March 24th.

[Pete Holmes]

March 24th is when it's available for free for anybody. You can pre watch it. When does this air? Before that?

[Chris Fleming]

Yes, definitely tomorrow.

[Pete Holmes]

Well, you can pre watch it on 800 pound gorilla's website. I think you can choose what you want to pay Radiohead style, pay a few bucks and watch it early. Or you can wait for the 24th. It'll be on my YouTube and £800 YouTube. And I'm really. I'm really proud of it. Like, who cares what you say? I. I mean, everybody was laughing.

[Chris Fleming]

Yeah.

[Pete Holmes]

And then we edit out the parts where they didn't.

[Chris Fleming]

So

[Pete Holmes]

Silly, Silly Fun Boy on YouTube.

[Chris Fleming]

Amazing. Thank you so much.

[Pete Holmes]

Thanks, guys.

[Chris Fleming]

That was so fun.