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.

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.

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." |

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

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.

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.

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