2 Bears, 1 Cave with Tom Segura & Bert Kreischer

Quote · 2 Bears, 1 Cave with Tom Segura & Bert Kreischer

Fat Tommy Vs Skinny Tom | 2 Bears, 1 Cave

Explore episode Jul 27, 2026

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Bill Hader, David Lee Roth & Boston Tea Party

At 28:10 · chapter starts 23:55

Bert builds the chapter around a theory: stories improve as they pass through people, because each teller is freed from the obligation of accuracy and can keep only the interesting bits. His proof is the David Lee Roth–Henry Rollins encounter. Rollins's original version is apparently long and unmemorable. Bill Hader's retelling is excellent. Bert's version — Rollins at a morning zoo radio station, Roth in a massive jacket filled with booze, offering beers at 6am, responding to Rollins's refusal with 'What's the matter, you got school later?' — may improve on both. Bert then pivots to a story from a weekend visiting his daughter Isla at college. He had explained the Boston Tea Party connection to America's coffee culture, and Isla casually remarked that she thinks about the Tea Party sometimes — it must have taken forever, having to brew all that tea just to throw it overboard. Then: 'I only brought one cup.' Bert retells it funnier than it actually happened, Isla protests, and Bert delivers his philosophy: it doesn't matter, everyone's entertained, what is life but a memory anyway?

Comedy
David Lee Roth vs. Henry Rollins at 6am

Fat Tommy Vs Skinny Tom | 2 Bears, 1 Cave · Jul 27, 2026 Comedy

Henry Rollins showed up to a morning zoo radio station at 6am to find David Lee Roth already in a floor-length jacket filled with booze, offering beers. When Rollins declined — he's notoriously sober — Roth shot back: 'What's the matter, you got school later?' The punchline gets better every time it gets retold.

Comedy
Isla's Boston Tea Party Theory

Fat Tommy Vs Skinny Tom | 2 Bears, 1 Cave · Jul 27, 2026 Comedy

Bert was explaining why Americans drink coffee instead of tea — the Boston Tea Party as a political act — when his daughter Isla calmly said she thinks about the Tea Party and how it must have taken forever to brew all that tea just to throw it overboard. Then she added: 'I only brought one cup.'

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