Jerry O'Connell Club Random with Bill Maher

Bill Maher welcomes Jerry O’Connell to Club Random with Bill Maher for a conversation that jumps from childhood fame to life in Calabasas. Jerry reflects on the unlikely moment that set his career in motion—when director Rob Reiner told the shy kid from Stand by Me to stop holding back and lean into who he was. That advice, he says, changed everything. From there, the two get into Jerry’s marriage to Rebecca Romijn, the surreal experience of being married to someone once married to John Stamos, and the chaos of raising teenagers in Calabasas. Along the way they cover Kourtney Kardashian’s parking etiquette, the Dean Martin school of zero rehearsal, and why ayahuasca is a hard no for both of them. Support our Advertisers: -Protect your car with CarShield. Get 20% off at with code RANDOM -Try Claude for free at -Try ZipRecruiter for free at

You can listen to Jerry O'Connell Club Random with Bill Maher online on Radio and Podcast. Open the player on this page to stream the available audio.

Jerry O'Connell Club Random with Bill Maher is an episode from Club Random with Bill Maher by Club Random.

This episode is 98:42 long.

This episode was published on Mar 16, 2026.

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