Pete Holmes Talks New Special ‘Silly Silly Fun Boy,’ Standup Craft, and Spirituality

February 28, 2026

AI Summary

5 min read

🎙️ The Voices & The Context

The Format: Casual podcast interview with host sharing personal anecdotes and clips, interspersed with ads.
The Key Players:
- Host: Johnny Mack, enthusiastic comedy podcaster who geeks out over specials, game shows, and Pete's career; great chemistry through shared comedy nerdery.
- Guest: Pete Holmes, acclaimed comedian known for HBO's Crashing, stand-up specials like Silly Silly Fun Boy, podcasting OG, and book Comedy Sex God; interesting for his thoughtful evolution from dick jokes to spirituality.
The Vibe: Fun, energetic, and educational—two comedy fans bantering insightfully on craft, with laughs, metaphors, and deep dives.

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What you'll learn

1 (00:00) **🎙️ Introduction: Pete Holmes**
2 (03:16) **Pyramid Game Show Memories**
3 (06:45) **Google Image Search and Retired Bits**
4 (09:35) **Crafting Stand-Up Specials vs. Live Sets**
5 (14:11) **Pacing for Streaming and Swearing Choices**
6 (20:45) **Stand-Up as Improvisational Art**
7 (22:54) **Podcasting, Hosting Montreal New Faces**

+ Full timestamped outline available in the app

Show Notes

Guest Pete Holmes discusses his new special “Silly Silly Fun Boy,” available via early access on 800 Pound Gorilla and later on YouTube Tuesday, March 24th.

They discuss Holmes’ success on “Pyramid,” including how seriously he takes the game, then segue into Google results featuring a “cannabis and tech today” image and Holmes’ decision to retire an older massage/dick-joke bit. Holmes explains how he structures and edits a special (cutting warmup, not moving closers), why swearing was heavier early due to the crowd’s energy, and that the special is cut from two shows in Portland. Conversation also covers hosting Montreal New Faces, standup as a living/jazz-like art, Holmes’ view of spirituality as experiential
awareness/consciousness, his comfort in his 40s, the early-2000s Chicago comedy scene, “Crashing” streaming, putting specials on YouTube, and his book title “Comedy Sex God.”

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