Tom and Bert dive into a whirlwind of conversations, from Tom's health scare and a brutal water fast to Bert's hilarious midnight antics on set. They explore the shifting landscape of late-night TV and podcasting, while celebrating the thrill of the upcoming NFL season. Humorous insights into their eating habits and the chaos of filming keep things light, alongside Bert's bold $1,000 betting plan on the Buccaneers. With plenty of laughs about family visits and unexpected surprises, this dynamic duo keeps the energy high!
01:07:26
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insights INSIGHT
Late Night Must Evolve Around Clips
Late night TV is losing cultural access because audiences follow celebrities more directly on social platforms.
Shows must be built for clips while preserving longer-format depth to remain relevant.
question_answer ANECDOTE
Shows Are Made For Shareable Moments
Both hosts observed late-night formats are optimized to pre-make shareable clips rather than long conversations.
They argued shows now design moments specifically to become viral clips.
question_answer ANECDOTE
Breaks Boost Creativity
Bert and Tom both felt refreshed after taking a break from weekly episodes and found their other projects thrived.
Bert discovered being offline made him more present, funnier, and less compelled to force weekly releases.
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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
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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
2 Bears, 1 Cave with Tom Segura & Bert Kreischer