Gambling With Our Lives | 2 Bears, 1 Cave

2 Bears, 1 Cave with Tom Segura & Bert Kreischer

2 Bears 1 Cave

Society & Culture, Comedy

4.8 • 23.2K Ratings

🗓️ 1 September 2025

⏱️ 65 minutes

🔗️ Recording | iTunes | RSS

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Summary

SPONSORS: - Don’t miss out on all the action this week at DraftKings! Download the DraftKings app today! Sign-up using https://dkng.co/bears or through my promo code BEARS. - For simple, online access to personalized and affordable care for Hair Loss, ED, Weight Loss, and more, visit https://Hims.com/BEARS - Upgrade to ShipStation today to get a sixty-day free trial at https://www.shipstation.com/cave Bert and Tom are BACK in the Cave! After a memorable summer takeover by Stavvy and Chrissy D, the OG Bears return to catch up on everything—movies, standup, gambling, insane diets, and why Bert can’t stop eating 10 egg bites at once. Tom opens up about his recent cancer-screening scare, which led to a brutal five-day water fast, and accidentally dropping 25 pounds while filming El Tigre. Bert shares why his watch doesn’t fit anymore, how he tormented his director by throwing Liquid Death cans at 4 AM, and the disgusting way he measures his weight. The Bears also dive into the future of late-night TV, Amy Poehler’s move into podcasting, their own TV and film projects, and Bert’s insane plan to bet $1,000 every week on the Bucs. Plus: family visits on set, Isla living like a diva in Bert’s trailer, Tom’s boys discovering fake cocaine, and both Bears gearing up for the upcoming NFL and NCAA football seasons! 2 Bears, 1 Cave Ep. 304 https://tomsegura.com/tour https://www.bertbertbert.com/tour https://store.ymhstudios.com Gambling problem? Call one eight hundred Gambler. In New York, call 8778HOPENY or text HOPENY (four six seven three six nine). In Connecticut, Help is available for problem gambling. Call eight eight eight seven eight nine seven seven seven seven or visit ccpg.org. Please play responsibly. On behalf of Boot Hill Casino & Resort (Kansas). Fees may apply in IL. Twenty-one plus age and eligibility varies by jurisdiction. Void in Ontario. Bonus bets expire seven days after issuance. See sportsbook dot draftkings.com/promos. NFL Sunday Ticket offer for new subscribers only and auto-renews until cancelled. Digital games and commercial use excluded. Restrictions apply. Additional NFL Sunday Ticket terms at https://youtube.com/go/nflsundayticket/terms . Limited time offer. Chapters 00:00:00 - Intro 00:00:07 - The Final Episode Of 2 Bears 00:09:36 - Tom's New Movie & Free Bert 00:21:47 - Why Tom Got So Skinny 00:33:23 - Bert Is Fat 00:42:04 - Family Visits + America's Team 00:45:48 - Bert's Big Bet 00:54:05 - Is Tom Down? 00:58:49 - A Bert Game Show? 01:01:45 - Wrap Up Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

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0:00.0	100%
0:01.2	Cheers
0:02.2	Welcome to the final episode ever of two bears one cave.
0:09.5	It was a blast while it lasted.
0:11.2	And we're here to sign off.
0:12.8	We thank Stavi and Chris DiStefano for taking over.
0:17.0	We know you enjoy them and you will continue to enjoy them.
0:20.5	Bert, good to see you.
0:25.5	Did you watch any other episodes? I would watch like, I saw parts of it. You don't watch any
0:33.7	fucking podcasts. That's true. But I did watch, I did watch parts of it. I started the first one. I watched about 25 minutes of it. And then I would pick up little parts of the other ones. Yeah. Did you watch them all? I watched everyone. I watched everyone. Yeah. No. Yeah, no. I watched the clips. I just know they were trashing us telling the whole time.
0:56.5	They were great. Stobby's so fucking funny, man. They're both.
1:00.4	DeStefano is, I think Chris is fucking hysterical. I think he's one of the funniest guys alive.
1:07.9	I totally agree. They're both just out of this world. Charismatic, funny. I mean,
1:14.2	they're so entertaining. Like, whenever I do a podcast with them or even see them socially,
1:18.7	it's always nonstop laughs. Did you see, did you see Chris on hosting Kimmel? I did. I watched
1:24.4	his monologue. Yeah. He was great. Fantastic. His monologue was so natural.
1:29.4	Yeah, he's, he's like, yeah, he's the man, dude. So fucking funny.
1:33.3	What do you think the model's going to be for saving the late night genre?
1:36.1	I think it's done. You think it's done? I don't think. Well, I mean, unless they complete, like, here's the thing.
1:42.2	When we were kids, you you know there was 25 channels and then
1:48.9	the late night format was the place for this comedy to see celebrities to have these
1:55.6	conversations like you know it was access to all that world now know, people follow those same people on TikTok,
	...

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