2 Bears, 1 Cave with Tom Segura & Bert Kreischer

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The OG Bears are back on this absolutely unhinged episode of 2 Bears, 1 Cave! Bert Kreischer and Tom Segura dive headfirst into VR porn disasters, accidental virtual orgies, and the terrifying realization that Oculus might actually be ending humanity.
Bert recounts a weekend alone that spirals into nine virtual orgies, soul-stealing eye contact, and panic-induced controller fumbling in a pitch-black room. The Bears also unpack loneliness, online hate comments, incel psychology, and how social media gives angry dudes a place to scream just to feel noticed.
From there, things somehow get deeper: wealth guilt, excess consumption, purging hundreds of shoes and jackets, Mounjaro weight loss, beating Jelly Roll in the next 2 Bears 5K, parenting chaos, friendship evolution, Jake Paul as a “god,” and why success is always part luck. Enjoy the Bears while they're here.

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https://www.instagram.com/chrisdcomedy/

2 Bears, 1 Cave Ep. 323

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Chapters
00:00:00 - Intro
00:00:14 - Bert's First Threesome
00:05:58 - Mean Comments
00:13:05 - Hanging With The Kids During Christmas
00:30:02 - Stroke Of Luck
00:34:11 - Excess & Purging Stuff
00:44:05 - Weight Loss, Mounjaro & Jelly Roll
00:55:15 - Jake Paul Is A God?
01:01:01 - Wrap Up

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It’s the final Winter Bears of the season, and Stavros & Chris are ringing in the New Year the only way they know how: complaining about first class, overeating pastries, and making terrible life decisions! As 2025 wraps, the boys reflect on blown resolutions, chaotic travel plans, New Jersey “vacations,” and Chris’ catastrophic decision to roast the entire Jersey Shore cast. Plus: Delta lounge politics, childhood SNL trauma, double-the-bread-double-the-head, and Stav helping Chris talk through the worst career choice he’s ever made.
Grab a croissant, buckle up, and celebrate the end of the Winter Bears era as we begin a new year!

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https://www.instagram.com/chrisdcomedy/

2 Bears, 1 Cave Ep. 321

https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://www.chrisdcomedy.com/
https://www.stavvy.biz/
https://store.ymhstudios.com

Gambling problem? Call one eight hundred Gambler. In New York, call 8778-HOPENY or text HOPENY (467369). In Connecticut, Help is available for problem gambling. Call 888-789-7777 or visit https://ccpg.org. Please play responsibly. On behalf of Boot Hill Casino & Resort (Kansas). Pass-thru of per wager tax may apply in Illinois. Twenty-one plus age and eligibility varies by jurisdiction. Void in Ontario. Restrictions apply. Bet must win to receive Bonus Bets which expire in 7 days. Minimum odds required. For additional terms and responsible gaming resources, see https://DKNG.co/audio. Limited time offer.

Chapters
00:00:00 - Intro
00:01:09 - First Class Complaints & Latent Homo Things
00:09:00 - New Years Resolutions
00:18:27 - Roasting The Jersey Shore Cast
00:28:45 - Workshopping Roast Jokes
00:39:43 - This Is Probably A Dumb Idea
00:45:02 - The Jersey Shore Photo Roast Session
00:51:31 - New Years Plans & NFL Roasts
00:55:00 - More "Fan" Questions
01:03:37 - Final Thoughts

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The Winter Bears Stavros Halkias and Chris Distefano return for another completely unhinged takeover of 2 Bears 1 Cave. With Tom Segura and Bert Kreischer nowhere to be found, the guys openly admit they once again didn’t prepare, and then immediately spiral into bread rankings, prostate exams, STD horror stories, religion, celebrity gossip, and the most deranged podcast business ideas ever pitched.
From focaccia-based trauma, to almost doing business with Jeffrey Epstein’s brother, this episode goes fully off the rails and never checks the map again.
Hit subscribe, brace yourself, and remember: this episode exists only because someone might need it someday.

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https://www.instagram.com/chrisdcomedy/

2 Bears, 1 Cave Ep. 321

https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://www.chrisdcomedy.com/
https://www.stavvy.biz/
https://store.ymhstudios.com

Chapters
00:00:00 - Intro
00:01:38 - Fat Boy Pastry Shop
00:07:42 - Just The Tip
00:11:53 - Sexually Transmitted Hilarity
00:25:13 - Family
00:31:15 - Third World Fun & Legendary Funbags
00:35:13 - Pimping Podcast Producers
00:43:42 - Doing Business With An Epstein
00:54:16 - Health Corner
01:01:52 - In Conclusion

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Merry Winter Bears-mas! Stavros Halkias and Chris Distefano take over 2 Bears 1 Cave while Tom Segura and Bert Kreischer are away, and immediately turn it into a holiday fever dream. The Winter Bears dive into chaotic Christmas traditions, Jewish Christmas supremacy, family trauma, weight-loss delusion, wild childhood memories, and the politics of gift-giving. Along the way, they spiral into ancestry revelations, Oldboy-level revenge fantasies, questionable parenting strategies, croissant mukbangs, and an all-time debate over the perfect Christmas Chinese food order. Grab a pastry and strap in — this might be the most unhinged holiday episode in 2 Bears history.

https://www.instagram.com/stavvybaby2
https://www.instagram.com/chrisdcomedy/

2 Bears, 1 Cave Ep. 320

https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://www.chrisdcomedy.com/
https://www.stavvy.biz/
https://store.ymhstudios.com

Chapters
00:00:00 - Intro
00:00:57 - Revenge & Christmas Plans
00:06:57 - The Germans Always Make Good Stuff
00:16:33 - Perfect Holiday Dinner Conversations
00:23:38 - Are Greeks Whites?
00:30:40 - Let's Eat Some Tommy Bunz
00:33:35 - Christmas Gifts
00:44:09 - Greek Thieves, Bribing Kids, & Daddy Stavvy
00:52:17 - Favorite Chinese Food Order
00:59:00 - Living The NYC Dream
01:02:28 - Answering Some "Fan" Questions

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Christmas CAME early! The Summer Bears are now the *Winter Bears* and they have returned to phone it in and fulfill some contractually obligated laughs. Chris Distefano and Stavros Halkias invade YMH Studios to talk awful breakfast decisions, Bert’s cruise from hell, fat-guy medicine science, Husky-induced life chaos, bombing on MTV, fighting GLP-1 drugs, Mike Tyson saving Big Pun at The Tunnel, and why both of them should never own pets, houses, or functioning digestive systems.
It’s chaotic, barely prepared, medically concerning, and absolutely perfect. Enjoy!

https://www.instagram.com/stavvybaby2
https://www.instagram.com/chrisdcomedy/

2 Bears, 1 Cave Ep. 319

https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://www.chrisdcomedy.com/
https://www.stavvy.biz/
https://store.ymhstudios.com

Gambling problem? Call one eight hundred Gambler. In New York, call 8778-HOPENY or text HOPENY (467369). In Connecticut, Help is available for problem gambling. Call 888-789-7777 or visit https://ccpg.org. Please play responsibly. On behalf of Boot Hill Casino & Resort (Kansas). Pass-thru of per wager tax may apply in Illinois. Twenty-one plus age and eligibility varies by jurisdiction. Void in Ontario. Restrictions apply. Bet must win to receive Bonus Bets which expire in 7 days. Minimum odds required. For additional terms and responsible gaming resources, see https://DKNG.co/audio. Limited time offer.

Chapters
00:00:00 - Intro
00:03:29 - Slutty Little Breakfast
00:07:14 - Podcast Polyamory
00:14:15 - Chrissy Housing Crisis
00:21:35 - Stavros Vs Fat Guy Medicine
00:31:48 - Fat Joe, Guy Code, & Graveyard Of Failed Shows
00:46:14 - Maybe The Worst Dog Ever
00:56:17 - Geopolitical Shenanigans & NYC Mayors
01:08:11 - Wrap Up

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