2 Bears, 1 Cave with Tom Segura & Bert Kreischer2 Jun 2025

Tom's Dad STOLE Dynamite & BLEW UP A Bridge w/ Barstool Big Cat | 2 Bears, 1 Cave

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 SPONSORS: - Make life easier by getting harder and discover your options at https://BlueChew.com! And we’ve got a special deal for our listeners: Try your first month of BlueChew FREE when you use promo code BEARS -- just pay $5 shipping. - If your revenues are at least in the seven figures, download the free e-book “Navigating Global Trade: 3 Insights for Leaders” at https://NetSuite.com/BEARS. - Sponsored by BetterHelp. Our listeners get 10% off their first month at https://betterhelp.com/bears 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 https://tomsegura.com/tour https://www.bertbertbert.com/tour https://store.ymhstudios.com 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 Learn more about your ad choices. Visit megaphone.fm/adchoices

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Episoder(329)

Ep. 160 | 2 Bears 1 Cave w/ Tom Segura & Quentin Tarantino

Bert Kreischer is still recovering from his heart surgeries so Tom Segura asked Quentin Tarantino to step in as a guest bear! Go check out Quentin’s new book “Cinema Speculation” and his podcast “The ...

21 Nov 20221h 28min

Ep. 159 | 2 Bears 1 Cave w/ Neal Brennan & Bert Kreischer

Neal Brennan joins Bert Kreischer in Tom Segura’s place for this episode of 2 Bears, 1 Cave. Neal and Bert discuss how much different comedians make, Neal’s Mark Twain speech, tour busses, SNL, repres...

14 Nov 20222h 7min

Ep. 158 | 2 Bears 1 Cave w/ Tom Segura & Bert Kreischer

It’s another week of 2 Bears, 1 Cave with Tom Segura and Bert Kreischer and it is a WILD episode! Sober October is over and it’s Berty Boy’s birthday! The Bears discuss their favorite comics and throw...

7 Nov 20221h 20min

Ep. 157 | 2 Bears 1 Cave w/ Tom Segura & Bert Kreischer

Happy Halloween! It's another week of 2 Bears 1 Cave with Tom Segura and Bert Kreischer and it's the last day of #SoberOctober! They discuss how unbelievably cool comedian Dean Delray is, the bears' f...

31 Okt 20221h 23min

Ep. 156 | 2 Bears 1 Cave w/ Tom Segura & Bert Kreischer

It's another week of 2 Bears, 1 Cave with Tom Segura and Bert Kreischer! They talk about Tiger Woods, their kids playing sports, and what it takes to become an elite athlete. They try to figure out ho...

24 Okt 20221h 20min

Ep. 155 | 2 Bears 1 Cave w/ Tom Segura & Bert Kreischer

We're halfway through Sober October and Bert Kreischer tells Tom Segura how he's disgusted with drinking now, the bears look at their sleep and recovery from Whoop, and Tom shares some VERY cool auto-...

17 Okt 20221h 16min

Ep. 154 | 2 Bears 1 Cave w/ Tom Segura & Greg Fitzsimmons

Greg Fitzsimmons is a stand-up comedian, writer, producer, and radio host. He joins Tom Segura, in Bert Kreischer’s place for this week’s episode of “2 Bears, 1 Cave.” They discuss their old acting cl...

10 Okt 20221h 34min

Ep. 153 | 2 Bears 1 Cave w/ Tom Segura & Duncan Trussell

Duncan Trussell joins Tom Segura in Bert Kreischer’s place for this week’s “2 Bears, 1 Cave.” They discuss the new Armie Hammer documentary, Vlad the Impaler, North Korea, UFOs, Mos Def, Ted Bundy, an...

3 Okt 20221h 25min