2 Bears, 1 Cave with Tom Segura & Bert Kreischer Podcast

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This week on 2 Bears 1 Cave, Tom Segura is joined by the legendary Jim Norton! The bears dive into Jim’s brand new special, why he no longer wants to be a cuck, and what it’s like to live shamelessly — including some very NSFW stories from Brazil.

Tom and Jim cover everything from a friendly Hitler and war documentaries to bombing onstage and the dark side of stand-up. They check out clips of Orson Welles’ drunk ad reads and William Shatner being difficult during a recording, and discuss JFK conspiracies, before pivoting to the power of charismatic maniacs like Jeffrey Epstein. Plus, Tom confronts his own comedy insecurities and Jim shares some Patrice O'Neal stories and breaks down the wildest moments from his years in radio. You don’t want to miss this one!

2 Bears, 1 Cave Ep. 294



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Chapters

00:00:00 - Intro

00:00:38 - It's Hitler Summer

00:05:41 - Comedy Special Edits, Self-Hatred, & Narcissists

00:16:41 - Embracing Shame

00:23:49 - Dopamine Release

00:30:01 - Orson Welles & William Shatner

00:38:27 - Favorite Interview Guests & JFK Conspiracies

00:43:50 - Epstein

00:50:10 - Bombing

00:56:30 - Headliners

01:02:27 - Patrice O'Neal Learn more about your ad choices. Visit megaphone.fm/adchoices

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This week on 2 Bears 1 Cave, Tom Segura and Bart Kersher are joined by rapper That Mexican OT! They kickoff the chat talking about Mexican food, burger spots, and That Mexican OT reveals a wild secret he has about eggs. On top of being super chill, That Mexican OT is a real authentic dude and he opens up about his very unique upbringing that helped shape who he is today. The trio discuss everything from hunting kangaroos to Japanese cholos, plus they also talk about bullfighting, gangster moms, pimp fathers, four wheelers, Project Recess! Grab some Por Osos and enjoy this episode!

2 Bears, 1 Cave Ep. 293

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Chapters 00:00:00 - Intro 00:04:16 - Mexican Food, Burger Places, & Eggs 00:10:47 - Kangaroo Hunting, Collabs, & Project Recess 00:19:56 - Bullfighting & Strippers 00:25:57 - Mom Scents & Med Shit 00:34:30 - Going International 00:40:18 - Authenticity & Growing Up Young 00:46:30 - Four Wheelers & Cholo Culture 00:52:26 - It's Scary Underwater 01:00:25 - Tough Guys 01:07:19 - Album Drop, Movies, & Rap Music 01:15:38 - Vodka Endorsement

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This week on 2 Bears 1 Cave, Tom Segura is joined by the hilariously unfiltered Mark Normand! The episode kicks off with farts and sharts as Mark shares the horrifying tale of sharting on a date right after letting one rip at the top of the show.

The Bears talk about parenthood, including Mark's brand-new baby, Tom's kids telling gay jokes, the absolute chaos of tiny humans mimicking adult behavior, and the innocence of youth. They next dive into Tom Cruise’s intensity, his popcorn-eating habits, and whether the man who saved cinema is also just a little…off. Then they go deep on comedy life: struggling in New York, open mics, internet haters, and the brutal truth that even legends get roasted.

Mark also shares more about life as a Brooklyn dad, falling asleep to podcasts, his time as a janitor, and a wild Copenhagen strip club story courtesy of Bert Kreischer. The conversation also hits on Tim Dillon's CNN moment, Sam Morril, Joe List, Vyvanse brain boosts, and weird dudes trying to get into business with Tom’s old corn star neighbor. Buckle up, queef it up, and enjoy!

2 Bears, 1 Cave Ep. 292

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Chapters 00:00:00 - Intro 00:00:35 - Sharts & Babies 00:05:08 - Tom Cruise 00:13:42 - Dad Stuff 00:20:12 - COMEDY! 00:27:22 - Hate From The Internet 00:33:42 - New York Comedy Scene 00:38:46 - Gay For Bert 00:44:41 - Conquering New York 00:51:03 - Right Man For The Job 01:00:10 - Texas 01:03:34 - Wrap Up

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Check out the newest podcast from YMH Studios "Not A Damn Chance"! Hosted by pro skateboarder Neen Williams and Michelin-starred chef Phillip Frankland Lee https://www.youtube.com/watch?v=ihy5odp5G9A

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This week on 2 Bears 1 Cave, Tim Segura and Bert Kershire are LIVE from the Barstool Chicago studio and share some stories of their latest shenanigans in the Windy City. The Bears also talk about bombing in Hawaii, jokes about slurs, fathers, women fading, whatever's going on in Bert's mouth, plus the internet hate for WNBA player Angel Reece and alleged royal Meghan Markle. The Bears are then joined by Big Cat who talks about stuff his kids are into lately and his favorite hobby aka gambling. Speaking of which, he also teaches the Bears about Dana White's infamous Tunnel of Chaos, before they pivot to the series "MobLand", and Tom shares a story about almost buying Dr. Dre's house. Bert also trash talks Tom's home base for some reason and compares us...I mean...it, to an abortion clinic or a dentist office, which, let me say is totally an exaggeration....I love working here. Enjoy the episode!

2 Bears, 1 Cave Ep. 291

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Chapters 00:00:00 - Intro 00:02:36 - Chicago Shenanigans 00:16:06 - Mouth Stuff 00:19:39 - Bombing Hawaii 00:29:01 - Friends 00:36:51 - Internet 00:43:28 - Women 00:49:04 - Big Words 00:59:18 - Mandela Effects 01:03:51 - Kids Stuff With Big Cat 01:12:09 - Gambling 01:20:42 - MobLand 01:24:17 - Work From Home 01:30:37 - Big Cat's Other Interests

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Check out the newest podcast from YMH Studios "Not A Damn Chance"! Hosted by pro skateboarder Neen Williams and Michelin-starred chef Phillip Frankland Lee

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This week on 2 Bears 1 Cave, Bert is on a retreat in Istanbul so Tom Segura is joined by the brilliantly bizarre Harland Williams for an unhinged episode packed with supposedly true stories, bootyholes, and too many farts. Harland kicks things off by reminiscing about fingering calamari and the first time someone touched his arse—with a thermometer. Tom shares the traumatic moment he had to show a friend his infamously hairy sphincter... and yes, he ends up showing Harland too.

Surprisingly, the conversation spirals into absurd territory with erotic drawings, smut searches, fart-catching attempts, a Dominican dick flash, and a deep dive into Enny’s alleged fondness for buttholes. Harland doesn’t disappoint either—he reacts to fart videos, tells a story about dating Madonna, and looks forward to tanning with Tom. The two also talk about creativity, recreational drugs, Harland's distrust of nicotine pouches, the anthems of both Canada and Texas, plus playing doctor, and horseshoes with neck pillows. Oh, and Harland names his favorite dictator. Stick around to find out if Harland ends up eating Tom.

2 Bears, 1 Cave Ep. 290

https://tomsegura.com/tour https://www.bertbertbert.com/tour https://store.ymhstudios.com

Chapters 00:00:00 - Intro 00:02:55 - Arses & Calamari Rings 00:14:34 - So Much Hair 00:26:10 - What's Going On With Canada? 00:31:24 - Measurements, Buzzes, & Vices 00:41:37 - Favorite Dictator 00:51:49 - Dating Madonna 00:55:46 - Clip: Baddie Farts 00:56:49 - Play Back The Tape 00:58:13 - Clip: Fart In One 00:59:29 - Tanning & Tour Dates 01:05:45 - Gas, Gashes, & Gruesome Videos 01:11:48 - Harland Wants To Eat Tom Learn more about your ad choices. Visit megaphone.fm/adchoices