2 Bears, 1 Cave with Tom Segura & Bert Kreischer

YMH Studios
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Nov 3, 2025 • 1h 18min

Duncan Trussell BLOWS Bert's Mind! | 2 Bears, 1 Cave

Duncan Trussell, a comedian and spiritual podcaster known for exploring philosophy and psychedelia, joins for a mind-bending conversation. They dive into the absurdity of Bigfoot, grapple with thoughts on death and AI, and discuss the concept of digital immortality. Trussell and Kreischer reflect on personal existence, humor as chaos magic, and the ethics of risky jokes. With a mix of hilarity and profundity, they explore the performative nature of comedy, the importance of audience connection, and finding joy despite life's uncertainties.
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10 snips
Oct 27, 2025 • 1h 11min

Tom Goes One-On-One With The Undertaker! | 2 Bears, 1 Cave

In a captivating conversation, Tom Segura chats with Mark Calloway, famed as The Undertaker, a WWE legend whose character has mesmerized fans for decades. They dive into Mark's unexpected journey from college basketball to wrestling, sharing behind-the-scenes stories from WrestleMania. Mark reveals insights on evolving his iconic persona, the physical toll of the sport, and the unique parallels between the life of a traveling comedian and a pro wrestler. Humor and heartfelt moments make this discussion a must-listen for wrestling and comedy fans alike!
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Oct 20, 2025 • 1h 25min

Robert DeNiro Didn't Wanna Be Friends w/ Sebastian Maniscalco | 2 Bears, 1 Cave

Sebastian Maniscalco, a stand-up comedian and actor known for his unique blend of observational and physical comedy, joins the discussion to share insights about his new special filmed at the United Center. The duo explores the emotional nuances of fatherhood and how it has changed Sebastian. There's a humorous dive into old-school comedy tales, including a light-hearted recollection of encounters with Robert De Niro. They also tackle the importance of staying passionate about comedy while finding a balance between fame and family life.
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Oct 13, 2025 • 1h 42min

Why Ice Cube Stays Mad in Every Movie w/ Funny Marco | 2 Bears, 1 Cave

This week, Funny Marco, a popular YouTuber known for his viral interviews, joins the discussion. He shares hilarious stories about interviewing celebs like Nicki Minaj and the surreal experience of sudden fame. The conversation dives into the psychology of fame, Ice Cube’s iconic angry roles, and even debates about the sexiest comedians. Marco reflects on maintaining authenticity in a world treating him as a brand and highlights the loss of anonymity that comes with fame. Expect laughs, sharp insights, and plenty of quotable moments!
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Oct 6, 2025 • 1h 5min

Tom and Bert's Favorite OF Submissions | 2 Bears, 1 Cave

Attention Hanover, MD! Tommy Buns is coming to The Hall At Live! Casino, Sunday, October 19. Get tickets now at https://tomsegura.com/tour SPONSORS: - As always, get your first month of BlueChew FREE Just use promo code BEARS at checkout and pay five bucks for shipping. https://bluechew.com -Sponsored by BetterHelp. Our listeners get 10% off their first month at https://betterhelp.com/bears - Download the CFO’s Guide to AI and Machine Learning for FREE at https://NetSuite.com/BEARS. This week, Bert and Tom dive headfirst into the weirdest brain rot rabbit holes yet — from testing out VR porn ("you can see her fillings!") to auditioning more OnlyFans submissions, one of which that includes… a unique Por Osos bottle cameo. The Bears also pitch a business idea for a grown-man “locker room,” debate how Bert's woke daughters compare to Tom's redneck sons, and discover the world’s wildest dogs and cats. Plus: Jelly Roll’s 5K transformation, Savannah cats that look like mini-lions, and Bert’s desperate plan to sneak another puppy past Leanne. It’s sex robots, freeze porn, fat-to-fit inspiration, and pet chaos all rolled into one classic 2 Bears, 1 Cave mess. 2 Bears, 1 Cave Ep. 309 https://tomsegura.com/tour https://www.bertbertbert.com/tour https://store.ymhstudios.com Chapters 00:00:00 - Intro 00:03:22 - Jimmy Kimmel and Tylenol 00:08:17 - New Interest 00:15:54 - What The Kids Are Into 00:27:48 - The Bears Draft A Prospect 00:38:32 - The Locker Room Experience 00:46:18 - Jelly Roll 00:52:10 - Cane Corso vs. Dogo Argentino vs. Savannah Cat 01:01:14 - Wrap Up Learn more about your ad choices. Visit megaphone.fm/adchoices
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43 snips
Sep 29, 2025 • 1h 16min

Phones Are Making You Unfunny w/ Jimmy Carr | 2 Bears, 1 Cave

Join sharp-witted stand-up comedian Jimmy Carr, renowned for his one-liners, as he discusses the world of comedy with Tom Segura. They dive into the impact of technology on culture and the phenomenon of 'cheap dopamine' from social media and porn. Carr shares his outrageous take on marijuana legalization for those over 50. The duo also reflects on the joy of live performances, contrasting it with the emptiness of online entertainment, and explores how modern dating has evolved. Expect laughter and insightful commentary on today's society!
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11 snips
Sep 22, 2025 • 1h 20min

James Gunn's Superheroes Are Flawed But Funny | 2 Bears, 1 Cave

James Gunn, the visionary director behind the Guardians of the Galaxy films and co-head of DC Studios, dives into the nitty-gritty of filmmaking. He shares the immense pressure of directing Superman and the sense of relief that followed its success. Gunn discusses the evolution of Peacemaker’s grounded storytelling and the importance of strong comedic material in reviving theater attendance. He also touches on casting challenges, the strategic planning of a decade-long DC universe, and the thrill of keeping filmmaking enjoyable.
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13 snips
Sep 15, 2025 • 1h 7min

Bert Calls His Dead Grandma | 2 Bears, 1 Cave

Join two comedic minds as they tackle everything from Bert's heartfelt tale about his late dog and his unexpected sister to the hilarious trials of cat ownership. They delve into the nostalgia of childhood prank calls, riff on trolling with real-world stories, and explore the wild side of VR addiction. With lively debates on OnlyFans submissions and a unique twist involving a call to Bert's deceased grandma, this podcast promises laughs and surprises galore. Plus, a deep dive into gambling and a quest for a shirtless golf buddy!
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9 snips
Sep 8, 2025 • 1h 8min

Is White-Face Cool Again? | 2 Bears, 1 Cave

Tom and Bert dive into Drewski's controversial 'whiteface' sketch and the evolving landscape of comedy. They engage in a spirited debate about heroism in the digital age, comparing military service with the rise of social media influencers. College football fandom brings out their nostalgic stories, while Bert hilariously claims he's among the top 0.5% strongest. Their chaotic plan to help an OnlyFans creator adds to the mayhem, probing the line between humor and cultural appropriation.
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21 snips
Sep 1, 2025 • 1h 7min

Gambling With Our Lives | 2 Bears, 1 Cave

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!

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