Pete Holmes Talks New Special ‘Silly Silly Fun Boy,’ Standup Craft, and Spirituality
Published: February 28, 2026
Duration: 43:27
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 Mon...
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 Mon...