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2 Bears, 1 Cave with Tom Segura & Bert Kreischer

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Next episode · Mon, Oct 26, 12:00 PM
06days 20hrs 12min 38sec

At the table this season

NEW Episode 344 · Season 1 Oct 19, 2026 · 1 hr 7 min

Shane Gillis vs SNL: Round 2 | 2 Bears, 1 Cave

SPONSORS: Visit https://betterhelp.com/bears to get 10% off your first month. Download the DraftKings Sports app and use code BEARS. New DraftKings customers can spend five and get two hundred in total bonuses paid within 21 days – includes all markets. Get up to $200 off Square hardware when you sign up at https://square.com/go/bears! #squarepod Get out there and enjoy the outdoors with Mountain Dew. An American Original. Tasting Great Since ’48. Look for Mountain Dew in stores near you. This week on 2 Bears, 1 Cave, Tom Segura and Bert Kreischer check in with Tom in Austin and Bert in New York for the Food & Wine Festival. Tom opens by tackling the Shane Gillis backlash from his SNL monologue, while Bert tries to stay out of it for once (he just really loves those pants). The Bears react to the livestreamed execution of the Fort Hood shooter getting called off. Then Bert declares himself Team Katie for new White House press secretary Katie Zacharia, from her shaky first briefing to her gym pics and the bar exam she failed, and the guys give her three months, tops. He also opens up about his people-pleasing after a woman on a plane Googles him and asks, "What did you do?" Plus: Condoleezza Rice's 9/11 story, Bert buying Napoleon's cologne in Paris, Pope Leo's surgery, a maintenance guy catching Bert's 54-year-old mirror selfie, Bert's street-interview do-over, Chris Distefano charming Rachael Ray on Something's Burning, and Mark Zuckerberg's first Guinness. 2 Bears, 1 Cave Ep. 344 https://tomsegura.com/tour https://www.bertbertbert.com/tour https://store.ymhstudios.com Gambling Problem? Call 1-800-426-2537, 1-800-697-3738. Connecticut: call 888-789-7777, visit https://ccpg.org/. On behalf of Boot Hill Casino in Kansas. Bet tax pass-through may apply in Illinois. 21+. Void in Canada. Event contract trading with DraftKings Predictions involves risk of loss. Availability varies. Predictions offer void in New York. Bet to get Bonus bets that expire in 7 days. Trade to get Predictions Dollars that expire in 1 year. $50 in rewards issued every 7 days via click to claim for 21 days. One non-withdrawable reward redeemable. Terms at https://dkng.co/audio. Limited time offer. Nationwide based on Sportsbook, Predictions, and Free-to-Play Sports Contest availability. Varies by State. Chapters 00:00:00 - Intro 00:00:58 - Shane Gillis' SNL Monologue 00:06:28 - Bert Stays Quiet For Once & Those Gym Pants 00:18:35 - The Fort Hood Shooter's Execution Gets Called Off 00:23:15 - Katie Zacharia & Condoleezza Rice's 9/11 Story 00:27:58 - The George Bushes & Napoleon's Cologne 00:35:03 - The Press Secretary Failed The Bar & Bert's Oval Office Plan 00:42:31 - "What Did You Do?" Bert Gets Googled On A Plan 00:48:25 - Pope Leo, Bert's Mirror Selfie, & The Street Interview Do-Over 00:56:50 - Chris Distefano Charms Rachael Ray 01:01:30 - Zuckerberg's First Guinness & Wrap Up Learn more about your ad choices. Visit megaphone.fm/adchoices

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