2 Bears, 1 Cave with Tom Segura & Bert Kreischer

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346 afleveringen, van nieuw naar oud

A Tiger Almost Ate Bert's Daughter | 2 Bears, 1 Cave

26 oktober 2026 · 54 min
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This week on 2 Bears, 1 Cave, Tom Segura and Bert Kreischer check in from Austin and New York. Bert lays out his plan to spend 24 hours with Mark Wahlberg alongside Rob Lowe, from 3 a.m. prayer to sleeping in Wahlberg's daughter's bedroom. Then Bert says his new hour finally clicked in Philadelphia, and the guys pull up the People magazine exclusive about his couples therapy with LeeAnn that Bert doesn't remember giving. From there, Bert tries to Google a photo of himself with Dolly Parton to prove to his daughters he really met her, and instantly regrets it. The Bears also get into Bert's bench press push-up challenge, getting drunk for the first time in nine months on Por Osos, and why LeeAnn keeps asking when he'll retire. Plus: why Tim Dillon is the funniest guy alive, Bill Burr in The Social Reckoning, Tom making the case for Tom Cruise's Digger, comedy as a belly flop contest, why you never turn your back on a tiger, and Bert's plan to keep a pygmy hippo at home.

2 Bears, 1 Cave Ep. 345

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Chapters

00:00:00 - Int…
Shane Gillis vs SNL: Round 2 | 2 Bears, 1 Cave

19 oktober 2026 · 1 uur 7 min
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This week on 2 Bears, 1 Cave, Tom Segura and Bert Kreischer check in with Tom in Austin and Bert in New York for the Food & Wine Festival. Tom opens by tackling the Shane Gillis backlash from his SNL monologue, while Bert tries to stay out of it for once (he just really loves those pants). The Bears react to the livestreamed execution of the Fort Hood shooter getting called off. Then Bert declares himself Team Katie for new White House press secretary Katie Zacharia, from her shaky first briefing to her gym pics and the bar exam she failed, and the guys give her three months, tops. He also opens up about his people-pleasing after a woman on a plane Googles him and asks, "What did you do?" Plus: Condoleezza Rice's 9/11 story, Bert buying Napoleon's cologne in Paris, Pope Leo's surgery, a maintenance guy catching Bert's 54-year-old mirror selfie, Bert's street-interview do-over, Chris Distefano charming Rachael Ray on Something's Burning, and Mark Zuckerberg's first Guinness.

2 Bears, 1 Cave Ep. 344

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The Sebastian Maniscalco SiriusXM Drama | 2 Bears, 1 Cave | 2 Bears, 1 Cave

12 oktober 2026 · 1 uur 11 min
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This week on 2 Bears, 1 Cave, Tom Segura and Bert Kreischer check in from the road, with Tom in Atlanta and Bert in Philly on his Permission to Party World Tour. The Bears debate whether they'll watch the Pentagon's livestreamed firing squad execution of the Fort Hood shooter, then dig into the SiriusXM Raw Dog Radio shakeup that had comics coming after Sebastian Maniscalco, and how one video turned into Bert starting a comedians union (Leanne is handling it). From there, Bert swears he'll die with his beard, finally tells Tom about the shot in Bad Thoughts season two he can't believe made the cut, and gets fired up over hood horse racing in Mississippi. Plus: Mike Ditka's one-take steakhouse commercial, Michael Jordan finding his lost championship rings in a forgotten safe, Chamillionaire's $25,000 autograph, Barry Sanders and The Fridge, and Tom getting pitched hair transplants.

2 Bears, 1 Cave Ep. 343

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Chapters

00:00:00 - Intro

00:06:15 - Should You Watch The Fort Hood Shooter's Execution?

00:12:14 - Black Horse Racing & Sprinting On A Horse

00:19:31 - Bert Will Die With This Beard & The Bad Thoughts Shot

00:24:52 - SiriusXM, Raw Dog Radio, & The Sebastian Maniscalco Backlash

00:35:19 - Bert's Comedians Union

00:41:25 - Spam Calls & Mike Ditka's One-Take Commercial

00:46:34 - Michael Jordan's Lost Championship Rings

00:56:52 - Barry Sand…
The Most Delusional Man In Comedy | 2 Bears, 1 Cave

5 oktober 2026 · 1 uur 11 min
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This week on 2 Bears, 1 Cave, Tom Segura and Bert Kreischer call in from opposite ends of the map: Tom on a day off from his movie in Atlanta, Bert from Cleveland's Rocket Mortgage arena. Bert pulls up old Hollywood stars next to today's to prove Tom belongs in Cocoon, and Tom fires back that Bert looks like ten pounds of shit in a five-pound bag. Then Bert drags in an arena worker to vouch for his looks, and she guesses Tom is 45. From there, the Bears lock in a bench press push-up challenge, Bert asks Claude who he should support between Israel and Palestine, before he finally admits to needing a seatbelt extender. They also get into Zach Bryan's Free Palestine shirt at Gillette Stadium, Ari Emanuel's memoir Roll the Calls, Bert's brutal gum surgery, Tom Cruise's Digger, and Tom introducing Bert to the cinematic universe of Quan Millz.

2 Bears, 1 Cave Ep. 342

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Chapters

00:00:00 - Intro

00:04:09 - Football, The Metric System, & Catching Strays

00:09:13 - Tom Belongs In Cocoon

00:16:07 - One-Drink Bert & The Bench Press Push-Up Challenge

00:28:11 - Cl…
Tom Cruise Pulled His Own Tooth Out w/ Rob Lowe | 2 Bears, 1 Cave

28 september 2026 · 1 uur 53 min
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This week, Tom is off somewhere, so Bert Kreischer is joined by the legendary Rob Lowe, back in the Cave to talk about his new movie The Musical, the Sundance comedy with a twist so audacious the big distributors were too scared to buy it, now playing in theaters. Rob breaks down the 18-day shoot, the moment that makes audiences gasp, and why a small theatrical run still beats a mystery streaming "hit." From there, the two get into learning stick on La Cienega, LeeAnn's endless story recaps, Tom Cruise pulling his own tooth for The Outsiders, and Paul Newman's legendary hangs. Bert opens up about his Free Bert season two meltdown and the night he forgot how to yawn, Rob shares what 36 years of sobriety taught him, and they pitch the ultimate Netflix show: 24 Hours with Rob & Bert, starring Mark Wahlberg as Dirk Diggler. Plus: Usher's house tour, Bryson DeChambeau's eagle, and the national anthem bit.

2 Bears, 1 Cave Ep. 341

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Chapters

00:00:00 - Intro

0…
Raygun Deserved The Gold Medal | 2 Bears, 1 Cave

21 september 2026 · 1 uur 13 min
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This week on 2 Bears, 1 Cave, Tom Segura and Bert Kreischer are on separate sides of the country, but still together in our hearts. Tom's about to film a movie and Bert's been running his takes through ChatGPT before he says them out loud, which still doesn't stop LeeAnn and his daughters from destroying him over The Pastor's Wife. Bert explains how Last Comic Standing edited him into the villain, and how much public misrepresentation a person should take before they swing back; Michael Jackson, Shane Gillis, Johnny Depp, Joe Rogan, and Bert's "how many bees until you start swatting" theory. From there, Bert delivers the two greatest analogies of his life, Tom demands the production Bible for Tenet to understand it better, and Bert turns his garage door into a guillotine. They also get into Kyle Forgeard of Nelk Boys running seven marathons in seven days, Bert's daughters hijacking his couples therapy to tell the therapist he only feels emasculated at Lowe's, and Bert's case that Raygun should have won the gold medal and that Jackson Pollock was a shill.

2 Bears, 1 Cave Ep. 340

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What Percent Gay Are You? | 2 Bears, 1 Cave

14 september 2026 · 1 uur 13 min
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Welcome back to the cave! Hunter Biden says he's 48% gay, which raises the only question that matters: what percent are you? Bert and Tom build the math from zero, clothes, dicks, physiques, saunas, eye patches, a $5,000 face laser, and Bert climbs a lot higher than he expected to.

Along the way: why Bert can't watch Sophie Cunningham highlights, the uncomfortable truth about loving Jason Williams, John Stockton's total lack of pizzazz, the hunt for a white DB in the NFL, Bert calling his dad mid-episode to check the family for slave owners (Tom's family does not come out clean), Bert's sister telling him to grow up about his sleep anxiety, Ila volunteering to fight Tom's ten-year-old in the Octagon, the 2:30am Dodger Stadium aftermath, a device that grades your poop, and Bert's full-throated defense of the Philadelphia Eagles' male cheerleader.

Plus: this week's Mountain Dew summer sizzle submissions, including one that requires $2.6 million of CGI and one that just shuts Bert up.

2 Bears, 1 Cave Ep. 339

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Jelly Roll Called The President A Fat Pig | 2 Bears, 1 Cave

7 september 2026 · 1 uur 14 min
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Welcome back to 2 Bears 1 Cave! This week Tom Segura and Bert Kreischer dive right in with Jelly Roll's headline-grabbing Kimmel monologue where he addressed the president as "from one fat pig to another." Bert then takes full credit for Jelly Roll's weight loss and the entire genesis of the Two Bears 5K, because technically he was in the room when that casually became a thing. They also have exciting news, a new 5K is coming in April and it's going to be bigger than ever.

From there, Bert opens up about the panic attacks he's been having, severe, physical, and rooted in something he now understands: a complete lack of childhood bedtime structure. Tom grew up getting nightly Catholic prayers, a sign of the cross from mom, and the full rosary in the car for any trip over ten minutes. Bert grew up watching Letterman alone at nine years old at 3am while his dad slept off a ten mile run. The bears compare notes on childhood bedtime routines, how they each put their own kids down now, and what sleep anxiety looks like when it hits a grown adult, including Bert's most recent 36-hour panic attack that started when a friend told him he yawns too much and he forgot how to do it. He couldn't yawn for a day and a half. He finally yawned in couples therapy. That's where we are.

They also get into Mel Gibson getting lightly canceled for mocking a sign language interpr…
Breaking Down The Barstool Brawl | 2 Bears, 1 Cave

31 augustus 2026 · 1 uur 46 min
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Tom Segura and Bert Kreischer are back in the cave and surprise surprise, Bert opens with a confession: he wishes he'd never quit drinking. What follows is a full inventory of the modern male brain, the online pastor Tom watches every morning to get inspired, why 17-year-olds have no business being nostalgic for anything, the exact moment each of them gave up on playing pro sports, and why comedians never seem to get that same reality check. The guys break down Bert's Whoop addiction and the blood clot that started it, get talked into a completely fictional performance-enhancing stack for a 5K, fall in love with bull riding legend JB Mauney, pitch the worst sponsorship idea in podcast history, and watch a food delivery driver take on the entire Barstool office. Then it's cringe cancellation, sobriety influencers, 4:23 a.m. morning routine guys, and a long, very funny argument about which movie stars are actually men and which ones just look at themselves in the mirror. Plus Bert's new fragrance obsession, the colognes of Napoleon, Elvis and JFK, Sebastian Maniscalco's four seasonal robes, Joe Rogan's splits, Billy Bob Thornton at the CMAs, and a big announcement about the future of the show.

2 Bears, 1 Cave Ep. 337

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Stavvy Called Us Out | 2 Bears, 1 Cave

24 augustus 2026 · 1 uur 26 min
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This week on 2 Bears, 1 Cave, Tom Segura and Bert Kreischer celebrate Bert officially entering the Guinness Book of World Records for The Machine, possibly the most performed signature story in comedy history, and immediately spiral into the comedy record arms race: Shane Gillis' 77,000-person show, Nate Bargatze's 2 million tickets, the Dane Cook vs. Dave Chappelle longest-set war, and Bert's plan to lock 75,000 paid "hostages" inside Raymond James Stadium and perform for ten straight hours. Then the Bears respond to Stavros Halkias calling out comics who fly private, and explain why he's absolutely right: nobody gets funnier on a private jet. From there, Bert declares Busboys, the new Theo Von and David Spade movie, the greatest piece of art he's ever seen, and Tom finally watches The Odyssey, only for Bert to officially turn on it over the Travis Scott cameo. Plus: Gaddafi's all-female Amazonian Guard, plane-crash hypotheticals, Chimp Empire is the best reality show ever made, Mick Jagger on fame, and why the Bears are grateful they got famous late.

2 Bears, 1 Cave Ep. 336

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Chapters

00:00:00 - Intro

00:00:18 - Co…
Tom & Bert's Brutally Honest Odyssey Review | 2 Bears, 1 Cave

10 augustus 2026 · 1 uur 2 min
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This week on 2 Bears, 1 Cave, Tom Segura and Bert Kreischer are back in the cave after eight weeks apart, and they open with a full review of The Odyssey, Lupita Nyong'o as Helen of Troy, Matt Damon's rogue Boston accent, and why Jon Bernthal is Hollywood's most legendary napper. From there, Bert unveils his billionaire rebrand (Sabah shoes, LBJ Stetsons, and the top five shoes billionaires wear this fall) before getting real about sobriety, anxiety attacks, and self-diagnosing 12 terminal illnesses in a single month. The Bears also spiral into the movies that blindsided them, Primal Fear, The Sixth Sense, Memento, Fight Club, and why the DIY hits like Obsession prove Hollywood is in another pivot moment. Plus: Project Hail Mary vs. the 15-hour audiobook, Bert's theory that this is the funniest (and most jacked) generation of comics ever, college football weight-room PRs, Jason Kelce showing up for a 9 AM bench session, and a meet & greet at MacDill Air Force Base August 14. If you missed the Bears, this one's for you.

2 Bears, 1 Cave Ep. 335

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Fat Tommy Vs Skinny Tom | 2 Bears, 1 Cave

27 juli 2026 · 1 uur 3 min
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This week on 2 Bears, 1 Cave, Tom Segura and Bert Kreischer compare their two very different eras of being fat, Tom's custom-made fat guy shirts, hard visceral fat vs. soft fat, and why losing weight made everyone think Tom got lip injections. Bert's sober documentary binge takes them from Patient Zero "Gay Tom" spreading AIDS across the Air Canada route map to Concorde pricing scams. Tom also reveals the fattest thing he's ever seen Bert do: ten appetizers, four entrées, and twenty doubles in Tallahassee. Bert also retells Bill Hader's retelling of Henry Rollins meeting David Lee Roth, and his daughter's instantly legendary Boston Tea Party take. Then things get real: a midlife crisis YouTube video sends Bert and LeeAnn into a "sell everything and get five apartments in five cities" fantasy, LeeAnn gets brutally honest about when she was happiest, and Tom breaks down the difference between happy and content. Plus: Hulk Hogan inflating Andre the Giant's weight, Julian's belt reaction to the Michael Jackson movie, Whoop resting heart rate brags, Craig Robinson's dunk, and the great first sweat vs. last sweat debate.

2 Bears, 1 Cave Ep. 334

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Chapters 00:00:00 - Intro00:00:52 - Fat Tommy Vs Skinny Tom00:09:16 - Patient Zero, Polio, & The …
Bert Gets Bullied By Lou Reed's Ghost | 2 Bears, 1 Cave

13 juli 2026 · 1 uur 14 min
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This week on 2 Bears, 1 Cave, Tom Segura and Bert Kreischer spiral through Bert's newest crisis: figuring out which musicians would actually like him. After Lou Reed tells him off mid-treadmill (entirely inside Bert's head), Bert starts deleting Jane's Addiction and Radiohead from his library, relives Shane Gillis walking out of a Wilco concert after five seconds, and learns his most-played song of all time is "Higher" by Creed. From there, the Bears get into Tom's tour of Kid Rock's 20,000-square-foot, two-bedroom replica White House and meeting Jimmy John from Jimmy John's, a deep dive on Subway Takes and why Bert believes celebrity hot takes are all fake, the viral "white people shouldn't sit on stoops in Bed-Stuy" debate, and a deeply satisfying story of a first-class line cutter getting humbled in front of Viola Davis. Bert also opens up about the final days of his five-and-a-half-month sobriety run, including the recovery books, journaling on planes, and why his first drink back is happening at his daughter Georgia's University of Oregon graduation before going scorched earth on the dad who posted his 4-year-old…
Tom Poops The Bucket, Bert Shit The Bed | 2 Bears, 1 Cave

29 juni 2026 · 1 uur 7 min
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This week on 2 Bears, 1 Cave, Tom Segura and Bert Kreischer dig into the wild, unexpected Black audience response to Bad Thoughts Season 2, Tom debuting his "out of your control" philosophy on how comedy lands, and a hilarious accounting of which comedians did and didn't text Bert about his new show. Bert opens up about getting nastier and setting harder boundaries in sobriety, comparing himself to the A-Rod and Rafael Nadal documentaries, and Tom reveals his ongoing health investigation that involves shitting in a bucket for a lab test. The Bears also spiral into a debate on regional diets and genetics, plan a mushroom trip with an actual shaman, get Bert's dad on the phone to discuss his own legendary history of public accidents, and revisit boys' locker room culture versus Gen Z's aversion to male nudity. Plus: a Mountain Dew summer sizzle reel callout to fans, a celebration-of-life merch drop business plan for when they die, and the most detailed bowel movement breakdown the show has ever produced.

2 Bears, 1 Cave Ep. 332

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Patrice O’Neal Destroyed Me | 2 Bears, 1 Cave

15 juni 2026 · 1 uur 16 min
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This week on 2 Bears, 1 Cave, Tom Segura and Bert Kreischer celebrate Por Osos landing in Publix just in time for the 4th of July, which sends Bert into a full nostalgic spiral about pub subs, boat days, and taking his daughters into "international waters." From there, things get historical, the bears break down the story of the guy who invented the meter and got guillotined for it, which leads them down a rabbit hole of people killed for their big ideas, the French Revolution as the original cancel culture, and Martin Luther versus the Catholic Church.Then Bert tells stories about his relationship with the late Patrice O'Neal: getting destroyed at his first open mic, the Edinburgh trip where they lived together for 29 days watching Bruce Lee movies and Bert getting his feelings systematically demolished, and the moment he found out Patrice had tweeted something kind about him right before the stroke. Tom and Bert also spiral deep into funeral planning, who's required to show up, who gets a Sandler video instead of a live appearance, why Ari's funeral is going to involve hardcore Brooklyn relatives and a lot of confusion, the Andrew Schultz balloon clown apology Bert wants delivered posthumously, and whether or not to get cremated when science might figure something out. Plus: horror m…
Nick Kroll Convinced Netflix to Air Animated Animal Sex | 2 Bears, 1 Cave

1 juni 2026 · 1 uur 45 min
Afspelen

Gape your 4th eye with Kurt Metzger and Duncan Trussell's new podcast Mystery Boys and get to the bottom of what's really going on in the world: https://www.youtube.com/playlist?list=PL-i3EV1v5hLfZinN-4ZV4wmZ862wupBWF Lees meer

Also, check out Tom's new bakery, Ciccio Bomba, at the new third location at 1100 South Lamar Blvd in Austin, right across from the Alamo Drafthouse.

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This week on 2 Bears 1 Cave, Nick Kroll joins Tom and Bert to break down his new Netflix animated series Mating Season, why animation produces tighter comedy than anything shot on the fly, and the emotional formula behind Big Mouth that turned a filthy puberty show into something people actually shed real tears for. Along the way, they get into an all-timer story from a legendary comedy industry gathering featuring basically every comic you've ever loved, Tom's Charlie Murphy sushi dinner story, Bert's 50-pound weight loss and very specific relapse date, a true urban legend about Michael Landon and a javelin, a genuinely compelling movie pitch called The Quad Squad, and somehow end up in a deep dive on the Eichmann trial, featuring Sir Ben Kingsley showing up to a table read entirely …
Live from the Rose Bowl | 2 Bears 5K ft. Jelly Roll, Ari Shaffir, Joe DeRosa & Are You Garbage?

18 mei 2026 · 1 uur 12 min
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The End is here! Ari's new storytelling show is $5.99 per episode at https://theend.ymhstudios.com. There's a total of 7 episodes for you to enjoy! Lees meer

Check out Joe DeRosa's new podcast Vile and Horrendous Pull up a chair and listen to what Joe does best: piss and moan! https://www.youtube.com/watch?v=bWvLI8xCAa0

Also, check out Tom's new bakery, Ciccio Bomba, at the new third location at 1100 South Lamar Blvd in Austin, right across from the Alamo Drafthouse.

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Live from the legendary Rose Bowl during Netflix Is A Joke Fest, the Bears are back and even sweatier than usual! Tom Segura and Bert Kreischer take the stage fresh off the 2 Bears 5K for a completely unhinged live episode packed with race stories, weight loss victories, comic cameos, chaos, and pure degeneracy.
Joined by Jelly Roll, Ari Shaffir, Joe DeRosa, and the guys from Are You Garbage?, the crew covers everything from losing hundreds of pounds and surviving airplane bathrooms while fat, to bidet discoveries, Netflix brunch disasters, H. Foley's iPhone nightmare, and the emotional insanity that surrounds the 2 Bears community.
Plus: Bert reveals he mailed busts of his own dick to his closest friends, Tom bombs in front of Eddie Murphy and lives to tell the tale, Ari returns from traveling the world with a sur…
The Bears Go Up In Smoke | 2 Bears, 1 Cave

4 mei 2026 · 1 uur 16 min
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The End is here! Ari's new storytelling show is $5.99 per episode at https://theend.ymhstudios.com. There's a total of 7 episodes for you to enjoy! Lees meer

Check out Joe DeRosa's new podcast Vile and Horrendous Pull up a chair and listen to what Joe does best: piss and moan! https://www.youtube.com/watch?v=bWvLI8xCAa0

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This week on 2 Bears, 1 Cave, Tim and Bart go up in smoke, sharing cigars together as they talk about whatever floats around in their collective heads. They talk about fat guy problems, before going into Tiger Woods' spiraling personal life. The Bears also walk down memory lane, comparing the infamous fat Bert pitching photo to one of him recently, and the drastic change is pretty staggering. They also unpack the text exchange between a student and the teacher sister of influencer Noah Beck, share some wild drug stories, and check out a clip of Doug Stanhope roasting a city council. Also the 2 Bears 5k is coming up! Hope you been training.

2 Bears, 1 Cave Ep. 328

https://tomsegura.com/tour

https://www.bertbertbert.com/tour

https://store.ymhstudios.com

Chapters

00:00:00 - Intro

00:01:56 - Fat Guy Problems

00:09:23 - Tiger Woods & Cigars

00:21:23 - Pitching Fat Pictures

00:29:30 - Noah Beck's Sister's Texts

00:43:40 - Age Differences

00:47:12 - Girl Talk

00:48:17 - Wild Drug Stories

00:59:19 - Doug Stanhope Fought City Hall

01:05:40 - Bren…
The End Is Here w/ Ari Shaffir | 2 Bears, 1 Cave

20 april 2026 · 1 uur 12 min
Afspelen

The End is Ari's new storytelling show! And it's finally here! Only at https://theend.ymhstudios.com/ . Get 7 full, hour long episodes of completely unfiltered stories for $29.99. Get it now! Lees meer

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Welcome back to 2 Bears 1 Cave! This week, Tom Segura and Bert Kreischer are joined by the always unpredictable Ari Shaffir, dropping in to promote “The End”, a bold, no-holds-barred storytelling series that serves as a spiritual sequel and final evolution of his cult-favorite show This Is Not Happening.This episode dives deep into Ari’s return to long-form storytelling, breaking down how The End was independently produced with a stacked lineup featuring top-tier comics and a unique profit-sharing model that actually pays performers. The trio reflects on the evolution of comedy since Ari's original show, from Comedy Central’s heyday to today’s creator-driven landscape. The conversation spirals into outrageous personal stories, behind-the-scenes industry insights, and hilarious debates about everything from sobriety culture to the lost art of live storytelling. There’s also an unforgettable deep dive into a near-collaboration with Tracy Morgan, a story that almost made it into final show, and the unhinged unseriousness of morning show promotional interviews. Check out The End, y'all! We legit worked hard on it her…
Somethings Burning And It's Bert's Bus | 2 Bears, 1 Cave

6 april 2026 · 1 uur 15 min
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The End is Ari's new storytelling show! It's almost here! Premieres April 16 on https://theend.ymhstudios.com/ . Presale pricing only available for a short time! You get 7 full, hour long episodes of completely unfiltered stories for $24.99. Afterwards, the price will increase so get it now! Lees meer

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Bert Kreischer and Tom Segura are back with a wild new episode of 2 Bears, 1 Cave, and this one has everything: a terrifying tour bus fire, Bert’s ongoing recovery from blood clots, near-death anxiety, celebrity gossip, and a heated defense of napping. Bert breaks down the shocking story of how his bus blew a tire outside Fargo, was left behind overnight, and then burst into flames just hours later — a moment that may have saved everyone on board. He and Tom unpack how close the situation really was, what Bert lost in the fire, and why he’s still obsessing over the hats.

The Bears also dive into Bert’s fear of flying, life on blood thinners, what it means to face mortality without booze, and the bizarre mental spiral that comes with multiple near-death experiences in a matter of months. From there, the conversation takes its usual chaotic turn into Club Shay Shay, the “lost everything and got it back” misunderstanding, the Je…
The Most Redacted Episode Ever | 2 Bears, 1 Cave

16 maart 2026 · 1 uur 17 min
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In this episode of 2 Bears, 1 Cave, Bert Kreischer and Tom Segura cover everything from Bert’s sorta sober lifestyle, weight loss, sleep improvement, and 5K training to marriage non-negotiables, separate bedrooms, and life on tour. The Bears also react to internet beef between Quentin Tarantino and Rosanna Arquette, joke about the Epstein files, discuss "kept women", talk Trump and Mar-a-Lago, share a tense aborted plane landing story, and spiral into one of their darkest and funniest hypothetical conversations yet. If you missed this show, this one's for you.

2 Bears, 1 Cave Ep. 325

https://tomsegura.com/tour
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Chapters
00:00:00 - Intro
00:01:19 - Bert's Weight Loss Journey
00:07:14 - Tarantino Beef & Unbothered Rogan
00:18:31 - Chef Drama
00:22:51 - Non-Negotiables
00:33:05 - Kept Women, Money, and Wild Relationship Logic
00:39:57 - Bert Learns He's In The Epstein Files
00:43:47 - Trump & Mar-A-Lago
00:50:07 - Dahmer & Plane Crashes
00:54:59 - How Would You Prefer To Die
01:02:23 - What Language Would You Prefer To Be Killed By?
01:06:55 - Racist Thing A Black Guy T…
Bert's Not Dead | 2 Bears, 1 Cave

9 februari 2026 · 1 uur 2 min
Afspelen

SPONSORS: Lees meer

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This week on Two Bears, One Cave, Tom Segura and Bert Kreischer spiral gloriously through brand loyalty, fast-food hot takes, donuts, Super Bowl commercials, health scares, and the kind of brutally honest conversations only best friends can have.
The Bears break down why Pepsi Zero Sugar might actually be better than Coke Zero, debate McDonald’s fries vs. literally everyone else, and revisit classic brand wars like Burger King vs. McDonald’s and Dunkin’ vs. Krispy Kreme. From Blooming Onion horror stories to why you should never order seafood at a steakhouse, this episode is packed with food takes that will absolutely start arguments.
Bert also opens up about his recent blood clot scare, panic attacks, medications, and how the experience completely shifted his perspective on health, mortality, and gratitude. The guys also talk sleep apnea machines, Benadryl addictions, Mounjaro side effects, testosterone confusion, and why medical advice somehow never agrees ever.
Plus: donut shop conspiracies in Los Angeles, Cambodian vs. Vietnamese sandwich excellence, Krispy Kreme’s wild history, Instagram’s “fatties eating” algorithm, tracking down Ari Shaffir in the jungle, and why the 2 Bears 5K might…
The End Of Humanity | 2 Bears, 1 Cave

12 januari 2026 · 1 uur 3 min
Afspelen

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- Protect your family with life insurance from Ethos. Get up to $3 million in coverage in as little as 10 minutes at https://ethos.com/BEARS. Application times may vary. Rates may vary.
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- Sign up for your one-dollar-per-month trial and start selling today at https://shopify.com/bears Lees meer

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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2 Bears, 1 Cave Ep. 323

https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com

Gambling Problem? Call 1-800-GAMBLER. New York: call 8778- HOPENY or text HOPENY. Connecticut: call 888-789-7777 or visit https://CCPG.org. On behalf of Boot Hill Casino in Kansas. Wager tax pass-through may apply in Illinois. Twenty one plus in most states. Void in Ontario. Restrictions apply. Bet must win to r…
New Year New Roast | 2 Bears, 1 Cave

5 januari 2026 · 1 uur 8 min
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SPONSORS:
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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 gam…
Pimping Podcast Producers | 2 Bears, 1 Cave

29 december 2025 · 1 uur 6 min
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- New Year, New Me! Get Huel for FIFTEEN PERCENT OFF with this exclusive offer for New Customers only with code BEARS at https://huel.com/bears (Minimum $75 purchase). Lees meer

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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Chris & Stavvy Save Christmas! | 2 Bears, 1 Cave

22 december 2025 · 1 uur 10 min
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- Order a bottle of Por Osos and some killer merch online https://drinkporosos.com Lees meer

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.

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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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The Summer Bears Came For The Winter | 2 Bears, 1 Cave

15 december 2025 · 1 uur 10 min
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- Sign up for a $1 per month trial period at https://shopify.com/bears. Lees meer

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!

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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 - Intr…
My Soul Will Always Be Fat | 2 Bears, 1 Cave

8 december 2025 · 1 uur 7 min
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This week, Bert’s wasting away, Tom’s tucking in his shirts, and the Bears are going into hibernation for the winter. Before that good news, Bert breaks down losing 25 lbs in a month, projectile-vomiting in airport bathrooms, and Tom producing Olympic-level protein farts. Tom also talks his new pastry empire and defends his son’s obsession with suits and hair product; along the way they dive into Bert’s DEXA scan nightmare, and some chaotic CMA stories including a Steve Martin panic-meeting and Billy Bob Thornton being a king. They also discuss robe culture, aging out of podcasting, comedian fashion, the future of 2 Bears with guest hosts, tours and the 2 Bears 5K, plus they announce the return of the Summer Bears next week. Enjoy!

2 Bears, 1 Cave Ep. 318

https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com

Chapters
00:00:00 - Intro
00:01:02 - OzemBert & Gassy Tim
00:09:17 - Fat Boy Dreams
00:19:35 - Dressing Like An Adult Is Hard
00:28:44 - Country Music Awards Chaos
00:39:57 - Robe Guys & Big Joe Pesci Energy
00:46:22 - Crisis Of Appearance
00:52:03 - Quentin Tarantino
00:55:46 - The Winter Bears, 2025 Look Back, & 2 Bears 5k
01:06:14 - Wrap Up

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The Dark Side of Internet Fame w/ Marcus King | 2 Bears, 1 Cave

1 december 2025 · 1 uur 28 min
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This week, Bert Kreischer sits down with musician Marcus King for a wild, emotional ride—naked ocean stories with Navy SEALs, cocaine confessions, microdosing mushrooms, Southern rock rankings, and why internet comments haunt grown men at 3AM. Plus: TikTok ruining music, therapy drunk, and Bert accidentally following people who hate him. Check it out!

2 Bears, 1 Cave Ep. 317

https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com

Chapters
00:00:00 - Intro
00:01:30 - Southern Rock & Creating Your Own Lane
00:07:01 - Marcus' Process, New Album, & Otis Redding
00:14:55 - Cigars With James Earl Jones
00:17:47 - Sobriety, Microdosing, & Losing the Sparkle
00:29:52 - Loving Yourself While The Internet Hates You
00:42:43 - Ranking Southern Rock Bands
00:49:44 - TikTok Ruining Music & Comedy
00:54:55 - It's Raining Tom
00:57:00 - Authentic Relationships
01:02:23 - The Most Realest Artists Out There
01:13:49 - Back To Top Southern Rock Bands
01:20:31 - Eulogies & Final Thoughts

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Louis C.K. on Writing His First Novel and Returning to Stage | 2 Bears, 1 Cave

24 november 2025 · 1 uur 9 min
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In this powerful and surprisingly emotional episode of 2 Bears 1 Cave, Tom Segura sits down with Louis C.K. to discuss his new novel Ingram, the creative process behind writing fiction, and the brutal emotional reality of loneliness and childhood struggle. Louis explains why he quit stand-up for over a year, how stepping away from the stage changed his life, and what ultimately pulled him back into comedy. Lees meer

The conversation dives deep into fear, pain, trauma, comedy philosophy, empathy, war stories, emotional burnout, and why the darkest moments in life can shape the most powerful art. Tom reveals that reading Ingram made him cry, and Louis talks about the deeply disturbing next book he’s finishing—including a scene that shocked even him while writing it.

They also explore the controversial idea of “punching down” in comedy, the ethics of humor, and why Louis believes the funniest material comes from the messy truth of being human.

2 Bears, 1 Cave Ep. 316

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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 eight eight eight seven eight nine seven seven seven seven 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 Ontari…
My Dad Was Probably A Murderer w/ Kirk Fox | 2 Bears, 1 Cave

17 november 2025 · 1 uur 9 min
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Tom Segura returns to the cave with the one-and-only Kirk Fox, comedian, actor, and possibly a future Supermax inmate, depending on how you interpret this episode. The two dive into Kirk’s accidental tennis-career-turned-acting path, his eccentric family upbringing (outdoor showers, blood-written memorials, and a grandma in a box), and his lifelong dream of becoming either an FBI profiler or a serial killer — whichever opportunity arrives first. Lees meer

From Waymo self-driving cars acting like drunk Uber drivers to territorial pissings, choke etiquette, BTK, Tommy Lynn Sells, Vince Champ the stand-up sex criminal, and a full breakdown of Supermax prison life, this episode spirals into a darkly hilarious masterclass on murder, consent, and why prison might actually be relaxing if you need more sleep.

If the FBI is listening — it’s all jokes. Probably.

2 Bears, 1 Cave Ep. 315

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Chapters
00:00:00 - Intro
00:01:34 - Tennis Legend Kirk Fox
00:08:40 - Charo Looks Like Bon Jovi
00:11:20 - Kirk’s Home Life
00:17:53 - Golden Showers
00:24:46 - More Killers & AI Sex Robots
00:33:42 - Tommy Lynn Sells & Killing by Train
00:37:43 - The Next Killer in Our Friend Group
00:40:49 - Supermax Prison Fantasy
00:46:29 - My Dad Was A Serial Killer
00:52:38 - Vince Champ: The Sex Crime Comedian
00:58:21 - Kirk’s FBI Dreams & Shamelessness
01:02:22 - Kirk & Tom Check Out Vince Champ's Comedy
01:06:07 - See You In Prison
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Mel Robbins Calls Out Bert’s People-Pleasing | 2 Bears, 1 Cave

10 november 2025 · 1 uur 59 min
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Tom will be filming his new stand-up special in Milwaukee at The Riverside Theater on November 14th & 15th! Tickets are still available in Milwaukee for the November 14th show. Go get your tickets now at https://tomsegura.com/tour . Lees meer

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This week, Bert sits down with the one and only Mel Robbins for a brutally honest, hilarious, and surprisingly deep conversation about anxiety, cheating, parenting, and learning how to “let them.” From wild college confessions to Mel breaking down her Let Them Theory in real time, this episode is half therapy, half comedy, and all chaos.
They cover everything — why Bert can’t stop overexplaining to strangers (and accidentally tried to kiss Nicole Kidman), how ADHD and anxiety shaped both of their lives, and why it’s so hard to stop caring what everyone thinks. Mel opens up about her own journey through debt, dysfunction, and discovery — and Bert realizes maybe, just maybe, he doesn’t have to fix everyone to be happy.
If you’ve ever felt like you’re juggling guilt, stress, and trying to please everyone — this episode will hit home and crack you up at the same time.

2 Bears, 1 Cave Ep. 314

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Chapters
00:00:00 - Intro
00:00:46 - What's Your Drink?
00:03:50 - College Chaos & Cheating Confessions
00:13:47 - Nobody Wants To F**k Up Their Life
00:23:12 - FOMO, Stoicism, & The Let Them Theory
00:34:42 - Why We Need to Disappoint People
00:47:55 - Family Guilt & The Dinner Dilemma
00:55:08 - An Awkward Nicole…
Duncan Trussell BLOWS Bert's Mind! | 2 Bears, 1 Cave

3 november 2025 · 1 uur 18 min
Afspelen

Tom will be filming his new stand-up special in Milwaukee at The Riverside Theater on November 14th & 15th! Tickets are still available in Milwaukee for the November 14th show. Go get your tickets now at https://tomsegura.com/tour. Lees meer

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- Eat smart at https://FactorMeals.com/bears50off and use code bears50off to get 50% off your first box, plus Free Breakfast for 1 Year.

Bert Kreischer celebrates turning 53 the only way he knows how — by spiraling into an existential and hilarious conversation with comedian and cosmic philosopher Duncan Trussell. From tales of Bigfoot and testicular cancer to deep dives on AI, death, main character syndrome, and whether any of us are even real, this episode swings from absurd to profound faster than Bert can take his shirt off. Duncan and Bert talk about everything — mortality, digital immortality, the illusion of self, performative living, and how comedy might be the purest form of chaos magic. Along the way, they share stories about Joe Rogan, Freddy Soto, and the strange spiritual beauty of making people laugh. There’s even a surprisingly thoughtful discussion about funerals, cruises, and the philosophy of “carpe diem.” Bert also reveals the truth about his infamous cruise (yes, the vodka shortage is real), his daughter’s fandom for Duncan, and why thumbnail culture might have “ruined podcasting.” Duncan, meanwhile, breaks Bert’s brain more than once with talk of Roko’s Basilisk, reincarnation, and smiling on the way to the gallows — all while making it sound like the funniest TED Talk you’ve ever heard. …
The Undertaker Goes One-On-One With Tom Segura! | 2 Bears, 1 Cave

27 oktober 2025 · 1 uur 11 min
Afspelen

Tom will be filming his new stand-up special in Milwaukee at The Riverside Theater on November 14th & 15th! Tickets are still available in Milwaukee for the November 14th show. Go get your tickets now at https://tomsegura.com/tour. Lees meer

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This week, Tom Segura sits down with WWE legend Mark Calloway — better known to millions as The Undertaker — for one of the most fascinating and hilarious deep dives ever on 2 Bears 1 Cave. From the grind of early wrestling days to the creation of one of the most iconic characters in sports entertainment, this episode is pure gold for wrestling fans and comedy lovers alike.
The Undertaker opens up about his unlikely path from college basketball to the squared circle, the wild meeting with Vince McMahon that birthed his legendary persona, and what it was like to rise through an era dominated by Hulk Hogan and other larger-than-life characters. He and Tom trade road-war stories, comparing the life of a traveling comedian to that of a pro wrestler — the endless travel, the brutal schedule, and the weird adjustment of coming home after months on tour.
Mark also reveals behind-the-scenes secrets of WrestleMania, his all-time favorite match with Shawn Michaels, and the brutal injuries (including being set on fire… twice) that came with three decades in the ring. Plus, he shares how he stayed committed to “living the character,” why he always wore black in public, and how he evolved The Undertaker over time to keep the mystique alive. They also discuss wrestling psychology, the art of storytelling in the ring, and the freakish athleticism of stars like Brock Lesnar, Kane, and Roman Reigns. From hilarious stories about stepping on te…
Robert DeNiro Didn't Wanna Be Friends w/ Sebastian Maniscalco | 2 Bears, 1 Cave

20 oktober 2025 · 1 uur 25 min
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TEXAS! Tom will be in Amarillo at the Amarillo Civic Center Complex on November 1st, then November 2nd in Lubbock at Buddy Holly Hall and El Paso at the Abraham Chavez Theatre on November 6th. Go get your tickets now at https://tomsegura.com/tour. Lees meer

SPONSORS:
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This week on 2 Bears, 1 Cave, Bort sits down with comedy legend Sebastian Maniscalco for one of the funniest, most honest conversations yet. They dive deep into Sebastian’s new stand-up special filmed at the United Center, what it takes to stay passionate about comedy, and how fatherhood changes everything.
From crying at movies and parenting philosophies to the “arrogance of boring” and buying boats, this episode is packed with heart, humor, and classic Bert chaos. The two swap stories about old-school comedy days, meeting Jerry Seinfeld and Robert De Niro, and the truth about balancing fame, family, and fun.

Tim will return next week...promise.

2 Bears, 1 Cave Ep. 311

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Chapters
00:00:00 - Intro
00:02:30 - Stand-Up, Sicilians, & Sensitivity
00:14:16 - Dressed To Impress
00:22:27 - Small Talk & Small Comedians
00:34:28 - Playing The Hits
00:39:30 - DeNiro & Casinos
00:46:20 - Wine, Wants, & Life Experiences
00:56:35 - Fun Dad & Discipline Dad
01:03:05 - Pete Correale
01:07:32 - Does Sebastian Do This?
01:16:06 - Married To An Artist
01:19:08 - Edit This Out! + Wrap Up

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

13 oktober 2025 · 1 uur 42 min
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Attention Hanover, MD! Tommy Buns is coming to The Hall At Live! Casino, Sunday, October 19. Get tickets now at https://tomsegura.com/tour Lees meer

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Bert Kreischer sits down with YouTuber and social media personality, Funny Marco for one of the most effortlessly hilarious and unexpectedly deep conversations on 2 Bears, 1 Cave. The two dive into everything from guessing celebrity ages and debating who the sexiest comedian is, to the weird psychology of fame, strip club etiquette, and why Ice Cube has never smiled in a movie.
Marco opens up about his viral interviews with Nicki Minaj and Orlando Brown, the surreal side of fame, and what it means to stay grounded when everyone treats you like a brand instead of a person. Bert shares behind-the-scenes stories from The Cabin and The Machine, his friendship with Katt Williams, and what it’s really like when fame takes away your freedom to “just go.”
Funny, sharp, and full of quotable moments, this episode swings from gut-busting comedy to surprisingly real talk about authenticity, anxiety, and why being “D-list famous” might be the sweet spot.

2 Bears, 1 Cave Ep. 310

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Gambling problem? Call 1-800-GAMBLER. In New York, call 877-8-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 …
Tom and Bert's Favorite OF Submissions | 2 Bears, 1 Cave

6 oktober 2025 · 1 uur 6 min
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Attention Hanover, MD! Tommy Buns is coming to The Hall At Live! Casino, Sunday, October 19. Get tickets now at https://tomsegura.com/tour Lees meer

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- 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

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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

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

29 september 2025 · 1 uur 16 min
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Attention Hanover, MD! Tommy Buns is coming to The Hall At Live! Casino, Sunday, October 19. Get tickets now at https://tomsegura.com/tour Lees meer

SPONSORS:
- Upgrade to ShipStation today to get a sixty-day free trial at https://www.shipstation.com/cave.
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This week, Tom Segura is joined by one of the greatest one-liner comedians in the world, Jimmy Carr!
Tom and Jimmy dive deep into the craft of comedy, comparing Carr's laser-focused joke construction to Bert Kreischer's chaotic storytelling. Jimmy reveals his controversial (and hilarious) take on
marijuana legalization—mandating it for people over 50—and the tragic role of "cheap dopamine" in modern life, from social media to porn. The conversation touches on global comedy culture, the
variable reward system that drives stand-up and casinos , and why the live comedy experience is 30 times funnier than watching a special alone. Jimmy Carr also gives his final, wishful prediction for how
Bert Kreischer will die. Plus: Why the 21st Century is just the 20th century on better screens, the long wait for GTA 6, Jimmy's hilarious interactions with Stephen Hawking, the importance of gratitude, and why Tom should have read the Quentin Tarantino book. Don't miss a conversation that is smart, insightful, and packed with the sharp, dark wit that only Jimmy Carr can deliver!

2 Bears, 1 Cave Ep. 308

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Chapters
00:00:00 - Intro
00:01:19 - The Mechanisms Of Reward
00:10:08 - The Spectacular Death Of Burt Kersher
00:15:51 - The Times They Are-A-Changing
00:28:51 - Weed Takes
00:37:22 …
James Gunn's Superheroes Are Flawed But Funny | 2 Bears, 1 Cave

22 september 2025 · 1 uur 20 min
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In this episode of 2 Bears, 1 Cave, James Gunn joins Tom Segura to talk filmmaking and the state of the entertainment industry. Gunn opens up about directing Superman, the pressures behind it, and the relief of its success. He also discusses his role as co-head of DC Studios, building a decade-long DC universe, and the bold choice to reshoot five and a half episodes of Peacemaker with a new Vigilante.
Tom and James bond over grounded storytelling, casting decisions, and the balance between comedy, superhero films, and CGI. They also touch on the return of comedies to theaters and how the industry continues to evolve.

2 Bears, 1 Cave Ep. 307

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Chapters
00:00:00 - Intro
00:00:45 - Peacemaker, El Tigre, & Grounded Aesthetics
00:08:24 - Big Screen Comedy
00:22:04 - Hitting The Creative Lottery With Superman
00:32:59 - The Writing Process & Juggling Big Budgets
00:41:16 - Special FX & Special Actors
00:47:57 - Batman
00:55:53 - Star Wars
01:00:12 - Guardians Of Fun
01:04:11 - Serious Filmmaking & "Ripley"
01:08:36 - Casting Highs & Lows

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Bert Calls His Dead Grandma | 2 Bears, 1 Cave

15 september 2025 · 1 uur 7 min
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Hey look, it's your favorite podcast hosts, Tom Segura and Bert Kreischer! This week in the cave Bert kicks things off with a brand-new joke he swears is the best thing he’s ever written, before diving into an emotional (and hilarious) story about his late bull mastiff, and the wild twist involving the family dog's long-lost sister. From there, the Bears riff on straight cat dads, Bert’s “sleep divorce,” VR porn addictions, childhood prank calls, and even the lost art of memorizing phone numbers. Bert even calls his dead grandma and chit chats with scam caller live on air.
The episode only gets wilder as Tom and Bert review real OnlyFans submissions from fans, debate who should be the first official “2 Bears OF star,” and spiral into some truly insane pitches that only these two maniacs could come up with.
Plus: speech impediments, Elmer Fudd racism, trolling stories, gambling breakdowns from NFL Week 1, and Bert trying to recruit Zac Efron into a shirtless golf fantasy with their new NIL athlete. This might just be the best episode of this show in a long ass time, don’t miss it.

2 Bears, 1 Cave Ep. 306

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Chapters
00:00:00 - Intro
00:01:41 - Dogs & Cats
00:08:59 - VR Corn
00:17:30 - Memorizing Geography
00:23:24 - Memorizing Phone Numbers
00:31:35 - Prank Calls
00:37:59 - We Got Some OF Prospects
00:49:50 - Speech Impediments
00:53:45 - NFL Week 1 Gambling
00:59:51 - Bert Wants To Adopt Athletes
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Is White-Face Cool Again? | 2 Bears, 1 Cave

8 september 2025 · 1 uur 8 min
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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.
- Don’t let financial opportunity slip through the cracks, get half off your first year with promo code BEARS at https://www.monarchmoney.com/bears
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We're sorry, guys! Tom and Bert are back in the cave with a full plate: Druski’s viral NASCAR “whiteface” sketch and the art of deep-cover character work, a big “Would you die for your country?” debate, and discuss why streaming giants (Kai, Adin, Jack, etc.) have completely remixed entertainment. Plus, Tom relives an electric college football weekend (FSU at home against Alabama = goosebumps), Bert admits he tried to move a 400-lb armoire and declared himself top 0.5% strong in the city, and the guys hatch a chaotic million-dollar plan to manage an OnlyFans creator—will it work? Is white-face really back? Is Bert making things up? Watch and find out!

2 Bears, 1 Cave Ep. 305

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https://store.ymhstudios.com

Gambling problem? Call one eight hundred Gambler. In New York, call eight seven seven eight HOPENY 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 https://ccpg.org. Please play responsibly. On behalf of Boot Hill Casino & Resort (Kansas). Twenty-one plus age and eligibility varies by jurisdiction. Fees may apply in Illinois. Void in Ontario. Bonus bets expire seven days after issuance. See https://sportsbook.draftkings.com/promos. NFL S…
Gambling With Our Lives | 2 Bears, 1 Cave

1 september 2025 · 1 uur 7 min
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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.
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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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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…
The Summer Bears Phone It In w/ Stavros Halkias & Chris Distefano | 2 Bears, 1 Cave

25 augustus 2025 · 1 uur 8 min
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SPONSORS:

- Eat smart at https://FactorMeals.com/bears50off and use code bears50off to get 50% off your first box, plus Free Breakfast for 1 Year.

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The Summer Bears’ reign has unfortunately come to an end! Stavros Halkias and Chris Distefano return for their last fill-in as hosts of 2 Bears 1 Cave, and they’re going out with a bang. From roasting Tom and Bert’s absence to spiraling into wild tangents about parenting, moving, sex robots, and pie diplomacy with the NYPD, this send-off is chaotic, hilarious, and the perfect finale.

Stavvy and Chrissy talk about the shock of how much fans loved their takeover, whether they’d ever come back as the Fall Bears, and even get Bert on the phone. Tom of course doesn’t pick up. But that's okay, because Mark Normand and Sam Morril crash the party near the end, bringing eclairs and stomach bugs to help close things out.

It’s been a wild six weeks, and the Summer Bears want to leave you with one last memory. You're welcome, f*ckers!

2 Bears, 1 Cave Ep. 303

https://tomsegura.com/tour

https://www.bertbertbert.com/tour

https://store.ymhstudios.com

Chapters

00:00:00 - Intro

00:01:01 - The Summer Bears' Last Dance

00:10:10 - Stoic Shit + Jump Scare Ad Break

00:17:14 - Moving Around & Finding Peace

00:24:12 - Bribing Cops With Pie & Being Addicted To Losing

00:33:06 - ChatGPT Sex Robots

00:41:26 - Swingers & Phoning It In With Bert

00:55:22 - Mark Normand & Sam Morril
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The Audience Is Gonna Hate Us w/ Stavros Halkias & Chris Distefano | 2 Bears, 1 Cave

18 augustus 2025 · 1 uur 16 min
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Stavros Halkias and Chris Distefano return for another sugar-fueled Summer Bears meltdown—this time with bagels, tiramisu, and enough food guilt to keep a Catholic therapist booked for years. The boys break down Chris’ ChatGPT pep talk, reminisce about Stavvy's golden toothless years, and spiral into a deep dive on Neapolitan ice cream fraud, gay NFL cheerleaders, and the politics of bagel orders. Also: Chris reveals his VO2 Max results from a flamboyant fitness coach who may or may not have called him “zaddy.”

2 Bears, 1 Cave Ep. 302

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Chapters

00:00:00 - Intro

00:01:00 - 2 Pigs, 1 Pen

00:12:45 - Catholic Guilt Vs Greek Shame

00:23:33 - Sexual Awakenings In Mom's Bed

00:30:31 - A Demeaning Offer & ChatGPT Pep Talk

00:43:50 - Social Media & Rage For The Gays

00:52:01 - Men In Women's Sports

01:00:02 - Zaddy Chris
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2 Bears, 1 Happy Ending w/ Stavros Halkias & Chris Distefano | 2 Bears, 1 Cave

11 augustus 2025 · 1 uur 11 min
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The Summer Bears are back and Chris Distefano and Stavros Halkias are fully locked into their takeover of 2 Bears 1 Cave. With Stav in a floral shirt and Chris squeezed into a Darryl Strawberry jersey, the two dive headfirst into tales of the wild ‘86 Mets, Kevin Spacey offering unsolicited shoulder rubs, and the horrifying science of ALS—because what’s funnier than degenerative nerve disease? Stavvy also gets a massage from Chrissy, we learn about Lenny Dykstra's podcast rates, and the guys debate polyamory, prostitutes, and just how many years Bert Kreischer has left.

Speaking of Bert, he sends the guys a morbid video asking them to predict which comedian friends are not long for this world. Plus, Stav makes a strong case for becoming a Japanese-style husband, Chris recounts a near-affair that lasted 12 seconds on the LIRR, and together they fantasize about future threesomes with suspiciously supportive fans.

Is it a good episode? No. Is it packed with fake current events, conspiracy theories, open marriages, and physical touch? You bet your bottom dollar it is.

2 Bears, 1 Cave Ep. 301

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https://store.ymhstudios.com

Chapters
00:00:00 - Intro
00:01:42 - Baseball Greats, Kevin Spacey, & ALS
00:10:31 - Reading Fan Comments
00:27:20 - Swingers, Cucks, & Flirty Fans
00:36:33 - Montreal Screwjobs & Polyamory Shenanigans
00:44:58 - Trisha Paytas Baby Theory
00:51:34 - Comedian Death Pool
01:00:49 - Chrissy Massages Stavvy
01:07:23 - Wrap Up

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Are We Trapped In This Podcast Forever? w/ Stavros Halkias & Chris Distefano | 2 Bears, 1 Cave

4 augustus 2025 · 1 uur 11 min
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-Get control of your overall finances with Monarch Money. Use code BEARS at http://monarchmoney.com for half off your first year
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The Summer Bears are back and sweatier than ever as Stavros Halkias and Chris Distefano return to the Cave for a milestone 300th episode that somehow combines deep psychological trauma, ass-eating, and cholesterol awareness in one glorious mess. Chrissy D reveals his shocking bedtime history with his mom, his late-night transition out of her bed, and how a surprise with a tongue changed the trajectory of his life—and his act. Stav explains how a 3XL shirt, childhood grilled cheese binges, and SNL reruns turned him into the hairy Greek sex symbol we know today.
The bears also dive into the state of late night TV (RIP), Jurassic Park boners, and why Bert and Tom might end up bankrupt with nothing but podcast houses and Uncrustables to their name. Plus, an unhinged Monarch Money ad read, BlueChew boners, Turkish military anal policies, and a heartfelt video message from Tom Segura himself. Are the Summer Bears destined to do this foever? Stay tuned!

2 Bears, 1 Cave Ep. 300

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https://store.ymhstudios.com

Chapters
00:00:00 - Intro
00:03:58 - Big Boy Shirts
00:10:15 - Tongue Punch Your Fartbox
00:19:21 - How Did This All Happen?
00:23:48 - Sleeping In Mom's Bed
00:37:17 - Stavvy's Hangups & Chrissy Late Night
00:48:27 - Bowel Movements & Old …
This Episode Is Getting Us Fired w/ Stavros Halkias & Chris Distefano | 2 Bears, 1 Cave

28 juli 2025 · 1 uur 8 min
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- Eat smart at https://FactorMeals.com/bears50off and use code bears50off to get 50 percent off plus FREE shipping on your first box.

Stavros Halkias and Chris Distefano are back for round two of Summer Bears—and things spiral immediately. Dressed in their finest “Queens County court appearance” outfits, the guys dive into tales of impersonating cops, awkward court appearances, and Chris’s brief career as a physical therapist (and even briefer run-in with medical malpractice).

The bears get uncomfortably honest about massages that went too far, AI-generated thirst traps, and whether or not Bert and Tom make smashable women. Plus: Stav drops knowledge about Benjamin Franklin’s revolutionary sexcapades, Chris reflects on losing MSG (but gaining perspective), and both dudes debate the pros and cons of fake tits, handy wives, and aging out of horniness.
It’s unhinged, unfiltered, and definitely leading to the hosts getting fired.

2 Bears, 1 Cave Ep. 299

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Chapters
00:00:00 - Intro
00:01:08 - Chrissy Court Date
00:06:15 - From Physical Therapy To Comedy
00:18:25 - Happy Ending
00:28:45 - Lady Tom & Bert
00:34:32 - Female Stavvy & Chrissy
00:43:55 - Handy Women & Unhandy Men
00:53:07 - Benjamin Franklin
00:58:32 - MSG
01:03:36 - Wrap Up

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The Summer Bears Takeover! w/ Stavros Halkias & Chris Distefano | 2 Bears, 1 Cave

21 juli 2025 · 1 uur 14 min
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SPONSORS:
- Upgrade your wardrobe and save on @trueclassic at https://trueclassic.com/BEARS! #trueclassicpod
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Tom and Bert are out for the summer, so Chris Distefano and Stavros Halkias are stepping in as your substitute Bears. In this unhinged takeover, they immediately derail the show with tales of cholesterol-fueled delusion, Nazi neighbors in Queens, circumcision conspiracies, radical acceptance, berberine powder, and why 4th of July is the real American holiday (sorry January 6).

The boys debate who’s the Bert and who’s the Tom in their pairing, accidentally rank the world’s races, and somehow end up talking about diabetes, Greek shame, and Japanese war crimes—all before diving into engagement stories, dad stress, and the magic of getting fat on purpose. Also, Bert checks in from his deathbed to interrupt and tells them to talk about Indian people. This episode is chaos in shorts. True summer vibes. No lessons, no structure—just greasy hot dogs, high blood pressure, and fat guy fun. It's going to be a wild summer!

2 Bears, 1 Cave Ep. 298

https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com

Chapters
00:00:00 - Intro
00:02:00 - Who's The Tom & Who's The Bert?
00:08:23 - The Gay Family Man
00:13:56 - Bert's Request
00:21:43 - My War Criminal Neighbor
00:27:19 - Epstein Lists, Toothless Looks, & Fat Guy Speedballs
00:34:49 - We're Just Slowly Dying
00:45:19 - Fourth Of July
00:53:33 - Radical Acceptance
00:58:53 - Chrissy D's Favorite Holiday
01:05:11 - Wrap Up

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Catfights Make The WNBA Interesting | 2 Bears, 1 Cave

14 juli 2025 · 1 uur 14 min
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This week on 2 Bears 1 Cave, Tom Segura and Bert Kreischer go deep on sports. They talk about Brett Favre's fall from grace, the greatness of the 2001 Baltimore Ravens, the unbeatable aura of Tony Siragusa, and the dynamic duo of Caitlin Clark and Sophie Cunningham. Before that, Bert shares some stories about going over to T-Pains house. The bears also discuss how violence has made the WNBA more watchable, how good the ESPN "30 For 30" documentaries are, and the most unbelievable races people participate in. Plus: Bert tells a story about how he almost chainsawed a leg off on skates, the Red Bull Flutag, rat catchers, Bert's chicken murder mystery, and more!

2 Bears, 1 Cave Ep. 297

https://tomsegura.com/tour
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Chapters
00:00:00 - Intro
00:01:17 - T-Pain
00:10:08 - Brett Favre: Hero Or Villain?
00:19:15 - Tony Siragusa & The 2001 Baltimore Ravens
00:30:38 - Caitlin Clark & Sophie Cunningham
00:37:58 - Bert Almost Lost A Leg Skating
00:42:28 - Red Bull Flutag
00:49:23 - The Most Insane Race
00:57:11 - Rat Collectors
01:05:54 - Chicken Murder Mystery
01:11:02 - Wrap Up

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We're Being Replaced! (For The Summer) | 2 Bears, 1 Cave

7 juli 2025 · 1 uur 12 min
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- 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.
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This week on 2 Bears 1 Cave, Tom Segura and Bert Kreischer reunite in sunny California for a jam-packed episode full of FOMO, fatherhood, and flaming hot air balloon disasters. The bears talk about Tom’s California vacation and getting into surfing with his boys. They dig into wild parenting comparisons, Luis J. Gomez’s insane training routines, and Bert feeling FOMO for Andrew Schulz’s perfect summer life on Instagram.

Tom then drops major news about shooting a new Netflix movie called El Tigre, which leads to Bert sharing his own plans for filming the series Free Bert in Atlanta. With both Bears tied up all summer, they announce special "Summer Bears" episodes and name the two hosts Chris Distefano and Stavros Halkias. Things get political (kind of) as Bert and Tom debate who should talk about world issues—spoiler alert: it’s not them. Bert then rants about the sheer terror of hot air balloons and Tom tells another legendary Top Dog tale about how he diverted a plane so he could take a piss. Buckle up—it’s a bumpy (and hilarious) ride.

2 Bears, 1 Cave Ep. 296

https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com

Chapters
00:00:00 - Intro
00:00:40 - Father FOMO
00:05:07 - The Summer Bears
00…

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The Most Delusional Man In Comedy | 2 Bears, 1 Cave

Tom Cruise Pulled His Own Tooth Out w/ Rob Lowe | 2 Bears, 1 Cave

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What Percent Gay Are You? | 2 Bears, 1 Cave

Jelly Roll Called The President A Fat Pig | 2 Bears, 1 Cave

Breaking Down The Barstool Brawl | 2 Bears, 1 Cave

Stavvy Called Us Out | 2 Bears, 1 Cave

Tom & Bert's Brutally Honest Odyssey Review | 2 Bears, 1 Cave

Fat Tommy Vs Skinny Tom | 2 Bears, 1 Cave

Bert Gets Bullied By Lou Reed's Ghost | 2 Bears, 1 Cave

Tom Poops The Bucket, Bert Shit The Bed | 2 Bears, 1 Cave

Patrice O’Neal Destroyed Me | 2 Bears, 1 Cave

Nick Kroll Convinced Netflix to Air Animated Animal Sex | 2 Bears, 1 Cave

Live from the Rose Bowl | 2 Bears 5K ft. Jelly Roll, Ari Shaffir, Joe DeRosa & Are You Garbage?

The Bears Go Up In Smoke | 2 Bears, 1 Cave

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Somethings Burning And It's Bert's Bus | 2 Bears, 1 Cave

The Most Redacted Episode Ever | 2 Bears, 1 Cave

Bert's Not Dead | 2 Bears, 1 Cave

The End Of Humanity | 2 Bears, 1 Cave

New Year New Roast | 2 Bears, 1 Cave

Pimping Podcast Producers | 2 Bears, 1 Cave

Chris & Stavvy Save Christmas! | 2 Bears, 1 Cave

The Summer Bears Came For The Winter | 2 Bears, 1 Cave

My Soul Will Always Be Fat | 2 Bears, 1 Cave

The Dark Side of Internet Fame w/ Marcus King | 2 Bears, 1 Cave

Louis C.K. on Writing His First Novel and Returning to Stage | 2 Bears, 1 Cave

My Dad Was Probably A Murderer w/ Kirk Fox | 2 Bears, 1 Cave

Mel Robbins Calls Out Bert’s People-Pleasing | 2 Bears, 1 Cave

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

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

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

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

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

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

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

Bert Calls His Dead Grandma | 2 Bears, 1 Cave

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

Gambling With Our Lives | 2 Bears, 1 Cave

The Summer Bears Phone It In w/ Stavros Halkias & Chris Distefano | 2 Bears, 1 Cave

The Audience Is Gonna Hate Us w/ Stavros Halkias & Chris Distefano | 2 Bears, 1 Cave

2 Bears, 1 Happy Ending w/ Stavros Halkias & Chris Distefano | 2 Bears, 1 Cave

Are We Trapped In This Podcast Forever? w/ Stavros Halkias & Chris Distefano | 2 Bears, 1 Cave

This Episode Is Getting Us Fired w/ Stavros Halkias & Chris Distefano | 2 Bears, 1 Cave

The Summer Bears Takeover! w/ Stavros Halkias & Chris Distefano | 2 Bears, 1 Cave

Catfights Make The WNBA Interesting | 2 Bears, 1 Cave

We're Being Replaced! (For The Summer) | 2 Bears, 1 Cave