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Season 2025
This week, Tom Segura and Bort Kreysher are joined by Ari Shaffir! The trio talk about Shaq's habit of Facetiming on the toilet, before deep diving into the drama surrounding Brianna
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This week, Tom Segura and Bort Kreysher are joined by Ari Shaffir! The trio talk about Shaq's habit of Facetiming on the toilet, before deep diving into the drama surrounding Brianna Chickenfry and Zach Bryan. Forgiving and forgetting is impossible for some people to do, ya know? The three guys next get into Ari's new special and return to Netflix, which gets interrupted by Bert going on a tangent about beefing with Black Twitter. They also discuss Protect Our Parks, making Joe Rogan proud, compliments from black people, Bert's bench bet, insurance being a total scam, serial killer fantasies, alternative news, and weirdo evil dudes like Diddy and Jared the Subway Guy.
WHAT'S EVERYBODY! It's another week of 2 Bears, 1 Cave with Tom Segura and Bart Chrysler! Los Angeles is being ravaged by wildfires right now, so Tom and Bert chime in on what's going
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WHAT'S EVERYBODY! It's another week of 2 Bears, 1 Cave with Tom Segura and Bart Chrysler! Los Angeles is being ravaged by wildfires right now, so Tom and Bert chime in on what's going and how serious the damage has been. The destruction has hit very close to home for them, so much so Bert's got himself a go bag ready by the door. The bears also talk about their kids playing sports, dumb shirts with pot leaves on them, ruining vacation photos, gifts for family, Tom's mom and sister both moving to Austin, Muslim fashion, a national uniform for people in America, clever Hollywood writers, and Nikki Glaser's Gold Globes hosting job. Bert also shares a story about Andrew "Dice" Clay asking him to keep his sons safe in LA, plus other stories from LA. Stay safe out there!
It's another week of 2 Bears, 1 Cave with Tom Segura being joined by guest bear, Adam "Pacman" Jones! "Pacman" is a former NFL cornerback and return specialist, who currently hosts The
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It's another week of 2 Bears, 1 Cave with Tom Segura being joined by guest bear, Adam "Pacman" Jones! "Pacman" is a former NFL cornerback and return specialist, who currently hosts The Pacman Jones Show, a streaming show on the BetOnline platform. Tom and Pacman talk about NFL shit talkers, the dirtiest players in the game, gaining confidence in your own skills, college football, spending money on dumb things, winning millions at the casinos, soft coaches, passing down wisdom to younger players, and golden toilets. Pacman also tells Tom about his dislike of Pittsburgh, his relationship with Cowboys owner Jerry Jones, and tells his side of the story about what happened the night of the Jake Paul/Mike Tyson fight. Enjoy!
It's another week of 2 Bears, 1 Cave with Tom Segura being joined by guest bear, comedian, actor, and influencer Druski! Tom opens the show doing his best impression of Magic Johnson,
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It's another week of 2 Bears, 1 Cave with Tom Segura being joined by guest bear, comedian, actor, and influencer Druski! Tom opens the show doing his best impression of Magic Johnson, much to Druski's amusement, before the two chat about Coulda Been Records, Druski's comedic American Idol-esque series that went from a joke to an actual global phenom. The duo also talk about touring around the world, career goals, Druski's ambitions, karate, sketch shows, fan engagement, and they bond over their mutual interest in Fancy Chef. Tom also introduces Druski to Robert Paul Champagne, they talk Alabama football, and Druski comes clean about what went down when he was invited to a Diddy party! Bert coulda been in this episode, but he was busy. Plus Druski abrupt leaves at the end of the episode...super random. Enjoy!
It's another week of 2 Bears, 1 Cave with Burnt Krystals being joined by guest bear, blink-182 drummer Travis Barker! The Bears just announced the return of the 2 Bears 5k in Tampa and
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It's another week of 2 Bears, 1 Cave with Burnt Krystals being joined by guest bear, blink-182 drummer Travis Barker! The Bears just announced the return of the 2 Bears 5k in Tampa and Travis is psyched for it, as he's become a running enthusiast over the years. In fact, he's got a 5K he's planning of his own going down in New Orleans THIS FRIDAY! Bert and Travis discuss the harrowing plane crash that Travis survived 17 years ago and how it changed his entire life. They also talk about riding around in tour buses, sharing the same bus driver, what motivators they like for marathons, the Kardashians, Joe Rogan's influence, meeting music greats, favorite tours, and rock star comedians, plus Travis also reveals his own unique tuna fish salad recipe! Try it out!
The bears are back together and Bert managed to keep all his toes. This week Tom and Bert talk medical updates, mortality, Bert's trip to Paris, and toxic rich person traits. Speaking of
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The bears are back together and Bert managed to keep all his toes. This week Tom and Bert talk medical updates, mortality, Bert's trip to Paris, and toxic rich person traits. Speaking of traits, Bert tumbles down a rabbit hole of self-diagnosis with Tom and has a realization that he may or may not have some sort of personality disorder. He suspects it's something called HPV or maybe it was HBP, I forget which one it was. Anyway, Bert has a therapy sesh with Tom, and then they talk about LeeAnn's country bumpkin attitude in France, social anxiety, Bert's plan to throw pennies around the city, the Hawk Tua girl's financial mistake, and much more!
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#276 - Saturday Night Live Secrets & Norm Macdonald w/ Kevin Nealon
Episode overview
It's another week of 2 Bears, 1 Cave with Burnt Krystals being joined by guest bear, the great Kevin Nealon! Tom is away looking into getting a hair job in Turkey or something, so Kevin
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It's another week of 2 Bears, 1 Cave with Burnt Krystals being joined by guest bear, the great Kevin Nealon! Tom is away looking into getting a hair job in Turkey or something, so Kevin is in to pick up the slack. Fresh off the SNL 50th Anniversary event, Bert and Kevin talk all about SNL and the funny group of friends that Kevin has had around him from there. They also talk about why comedy was their calling, how long Bert can keep up the shirtless thing, gifting people sharp objects, aging with fans, staying fit, and Kevin Nealon speaking at Garry Shandling and Norm Macdonald's respective funerals. Kevin and Bert also swap Norm stories and Bert impresses with his investigative journalist skills.
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#277 - Married To The Queen Of Garbage w/ Kevin Ryan & H. Foley (Are You Garbage?)
Episode overview
It's another week of 2 Bears, 1 Cave with Tom Segura joined by a pair of guest bears, the Are You Garbage? boys Kevin Ryan and H. Foley! They've got a documentary special coming out and
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It's another week of 2 Bears, 1 Cave with Tom Segura joined by a pair of guest bears, the Are You Garbage? boys Kevin Ryan and H. Foley! They've got a documentary special coming out and they talk all about the intimacies of behind the scenes moments and the classic comedy bit of shitting your pants on camera. Christina P had the pleasure of recently appearing on Are You Garbage and the trio give the "Queen of Garbage" her flowers. They also talk about how insane Philadelphia got when they won the Super Bowl, the importance of mean old coaches, getting thrown out of restaurants, financial goals, being a big baller when the bill comes, shady banks, and the homicidal shenanigans of Tom's kids. Check it out!
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#278 - Chrissy Crypto Explains Bitcoin w/ Chris Distefano
Episode overview
In this wild episode of 2 Bears 1 Cave, Bert Kreischer flies solo—well, almost. He’s joined by the hilarious Chris Distefano for a chaotic, high-energy conversation that somehow covers
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In this wild episode of 2 Bears 1 Cave, Bert Kreischer flies solo—well, almost. He’s joined by the hilarious Chris Distefano for a chaotic, high-energy conversation that somehow covers everything from colon health to Benito Mussolini.
Chris introduces Bert to the Yuka app and starts scanning his diet, exposing just how questionable his food choices really are. They dive into couple’s therapy, hair loss in men, and Bert’s “child in flip-flops" fashion sense. The two also get deep on career goals in comedy, grinding in the industry, and the "Luigi Mangione of Serbia".
But it wouldn’t be 2 Bears without some unhinged history talk—Bert and Chris go off on a tangent about the history of currency, Bitcoin, the time Nazis packed Madison Square Garden, and the Axis Powers (because, why not?). They also touch on Florence, Italy, young people thinking Democrats are gay, and how their families keep them grounded. Strap in, grab a drink (or a Yuka-approved snack), and enjoy the show!
In this wet and mild episode of 2 Bears 1 Cave, Tom Segura and Bert Kreischer are back together to catch up on everything that's been going on since the last time they were face to face.
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In this wet and mild episode of 2 Bears 1 Cave, Tom Segura and Bert Kreischer are back together to catch up on everything that's been going on since the last time they were face to face. They debate who the strongest comedian is, Bert claims it's himself, Tom suggests Godfrey or Carrot Top. Who do you think it is? The bears also talk about how cities kind of blow, Bob Dylan sorta sucks, Mussolini inventing fascism, Bert's big summer plans, Chrissy D performing at MSG on 9/11, plus some Oscars thoughts, some opinions on refrigerated food, and the different flavors of Spanish around the world. Enjoy the show!
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#280 - The Hottest & Baldest Episode Ever w/ Sean Evans
Episode overview
Sean hosts the hottest interview show Hot Ones and sits in the interview chair to play Tom's own version of Hot Ones, except it involves scrotum sniffing...you'll see. The two chat about
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Sean hosts the hottest interview show Hot Ones and sits in the interview chair to play Tom's own version of Hot Ones, except it involves scrotum sniffing...you'll see. The two chat about how the show has become a cultural phenomenon, the legacy of Chicago sports, Sasquatch, handwritten Quentin Tarantino scripts, weathermen, deep dish pizza, the Oscars, Bryce Mitchell, trustworthy news anchors, and Tom reveals when he will finally start watching "Severance". Sean also tells a cool story about how he became friends with Dave Grohl despite being kinda responsible for him shitting himself.
Bert and Tom take 2 Bears 1 Cave on location at SXSW, broadcasting straight from The Portal, a Por Osos sponsored party house—where the drinks are flowing, fans are mingling, and people
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Bert and Tom take 2 Bears 1 Cave on location at SXSW, broadcasting straight from The Portal, a Por Osos sponsored party house—where the drinks are flowing, fans are mingling, and people are literally jumping off the roof into the pool.
The chaos kicks off as Bert calls back to an insane AI-generated video called "Fat N-word Season," that does in fact exist. From there, they tackle the big questions in life, like what is the perfect boob size and do Black guys really not always fit all the way in during intercourse?
They also get deep about comedians being forgotten in pop culture history, before immediately pivoting to Bert’s questionable SXSW outfit and how he narrowly avoided disaster with Magic Johnson. Ari Shaffir’s name comes up, Bert lays some praise on Tom for his Robert Smith costume on YMH Live X, and Tom tries to wrap his head around Bert becoming friends with Mel Gibson at a UFC event—which might just be the most Bert Kreischer thing ever.
Joey "CoCo" Diaz is back, baby! This week on 2 Bears 1 Cave, Bert Kreischer welcomes the legend himself, Joey Diaz to join him in the cave. Uncle Joey recently had a health scare and was
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Joey "CoCo" Diaz is back, baby! This week on 2 Bears 1 Cave, Bert Kreischer welcomes the legend himself, Joey Diaz to join him in the cave. Uncle Joey recently had a health scare and was forced to spend some time in the hospital. He's doing alright now, but the worst part about it all was the blue balls and repressed feelings of horniness he felt. Jose and Bart also talk about falling back in love with comedy, slowing down your touring, the mass comedy exodus of Los Angeles, moving during a pandemic, the early days doing comedy with Rogan, the best Ralphie May stories, comic actors, saying whatever you want, and how important parking spots are in major cities.
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#283 - Kill Tony Hits Netflix & Kyle Dunnigan’s Most Hated Impression
Episode overview
This week on 2 Bears 1 Cave we have Tom Segura and guest bear Kyle Dunnigan! After both appearing on "Kill Tony: Kill Or Be Killed", now streaming on Netflix, they've got some thoughts
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This week on 2 Bears 1 Cave we have Tom Segura and guest bear Kyle Dunnigan! After both appearing on "Kill Tony: Kill Or Be Killed", now streaming on Netflix, they've got some thoughts and reactions from that insane event to share with of you. They also discuss Kyle's weird dating history, his interest in taller women, and how he finds dates in a world of dating apps. Kyle also has a massive collection of impressions he unloads, including Caitlyn Jenner, RFK Jr, Joe Biden, and the infamous Bill Maher impression that Bill Maher just absolutely loves okaaayy. They also exchange stories about bombing at private events and Kyle tells Tom all about the time he worked Tony Robbins' weird birthday party. Lot of stories, lot of impressions, check it out!
This episode has no summary.
This episode has no summary.
This week on 2 Bears 1 Cave, Bert Kershire and Tim Segura are hooked up to IV's as they recover from their gay bar takeover and all the love the received from all those hungry bears.
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This week on 2 Bears 1 Cave, Bert Kershire and Tim Segura are hooked up to IV's as they recover from their gay bar takeover and all the love the received from all those hungry bears. They talk Instagram FOMO, the magic of minority women making meals for their husbands, a chola influencer named La Sleep that Bert is obsessed with, and the performative nature of social media. They also talk about the appeal of the Kelce brothers to gays, share the unique name of a cocktail that was invented at the takeover, debate which group of people gives the best compliments, and finally they tackle the subject of sampling your own sauce, which means exactly what you think it means. Enjoy the show!
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#286 - The Blue Origin Broads Backlash w/ Thomas Lennon
Episode overview
This week on 2 Bears 1 Cave, Bert Kreischer is joined by legendary funnyman and certified bear Thomas Lennon for one of the wildest rides yet. No stranger to confrontations, Thomas tells
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This week on 2 Bears 1 Cave, Bert Kreischer is joined by legendary funnyman and certified bear Thomas Lennon for one of the wildest rides yet. No stranger to confrontations, Thomas tells Bert some stories about a fight he got into in the real-world and the internet. They dive into the Amazon reviews of Mein Kampf, unpack the all-female Blue Origin space flight, and debate which celebs should be launched into orbit next.
Thomas also opens up about working with Christopher Nolan, shares the weirdest thing he’s ever used his fame for, and the two squirm over some spelunking stories. The two also discuss claustrophobia, Tom's basketball injury, suicide pods in Switzerland, and whether getting beat up by a woman is a fair fight. From film criticism to Karen moments, to the legendary Pink Palace, this episode has it all!
On this episode of 2 Bears, 1 Cave, Tom Segura is joined by the legendary storyteller himself—MrBallen! Get ready for an epic conversation as they dive into some of the wildest true
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On this episode of 2 Bears, 1 Cave, Tom Segura is joined by the legendary storyteller himself—MrBallen! Get ready for an epic conversation as they dive into some of the wildest true crime mysteries and horror stories, including the chilling unsolved case of the Yuba County Five and a gruesome incident on an oil rig that will haunt your dreams.
They also explore mind-blowing topics like habitable exoplanets, Katy Perry’s space adventure, and MrBallen’s incredible journey from Navy SEAL to YouTube sensation.
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#288 - Ripping Beers & Running 5K's w/ Jason Kelce, N.O.R.E, and Beau Allen
Episode overview
This week on 2 Bears 1 Cave, Tom Segura and Bert Kershire are LIVE from the 2 Bears 5k in Tampa Bay Florida! They aren't alone either, the bears are joined by not one, not two, but three
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This week on 2 Bears 1 Cave, Tom Segura and Bert Kershire are LIVE from the 2 Bears 5k in Tampa Bay Florida! They aren't alone either, the bears are joined by not one, not two, but three guest bears! Joining Tom and Bert are rapper/running enthusiast N.O.R.E, as well as, former NFL players/Super Bowl champs, Jason Kelce and Beau Allen. The group all get together to talk about the real challenges of the 2 Bears 5k, who the best drinkers are, running, nicknames, dictators, Hype Williams, stupid purchases, and so much more.
This episode has no summary.
This episode has no summary.
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#290 - Tom Shows Harland Williams His Chocolate Starfish
Episode overview
This episode has no summary.
This episode has no summary.
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#291 - Tom's Dad STOLE Dynamite & BLEW UP A Bridge w/ Barstool Big Cat
Episode overview
This week on 2 Bears 1 Cave, Tim Segura and Bert Kershire are LIVE from the Barstool Chicago studio and share some stories of their latest shenanigans in the Windy City. The Bears also
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This week on 2 Bears 1 Cave, Tim Segura and Bert Kershire are LIVE from the Barstool Chicago studio and share some stories of their latest shenanigans in the Windy City. The Bears also talk about bombing in Hawaii, jokes about slurs, fathers, women fading, whatever's going on in Bert's mouth, plus the internet hate for WNBA player Angel Reece and alleged royal Meghan Markle. The Bears are then joined by Big Cat who talks about stuff his kids are into lately and his favorite hobby aka gambling. Speaking of which, he also teaches the Bears about Dana White's infamous Tunnel of Chaos, before they pivot to the series "MobLand", and Tom shares a story about almost buying Dr. Dre's house. Bert also trash talks Tom's home base for some reason and compares us...I mean...it, to an abortion clinic or a dentist office, which, let me say is totally an exaggeration....I love working here.
The episode kicks off with farts and sharts as Mark shares the horrifying tale of sharting on a date right after letting one rip at the top of the show.
The Bears talk about
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The episode kicks off with farts and sharts as Mark shares the horrifying tale of sharting on a date right after letting one rip at the top of the show.
The Bears talk about parenthood, including Mark's brand-new baby, Tom's kids telling gay jokes, the absolute chaos of tiny humans mimicking adult behavior, and the innocence of youth. They next dive into Tom Cruise’s intensity, his popcorn-eating habits, and whether the man who saved cinema is also just a little…off. Then they go deep on comedy life: struggling in New York, open mics, internet haters, and the brutal truth that even legends get roasted.
Mark also shares more about life as a Brooklyn dad, falling asleep to podcasts, his time as a janitor, and a wild Copenhagen strip club story courtesy of Bert Kreischer. The conversation also hits on Tim Dillon's CNN moment, Sam Morril, Joe List, Vyvanse brain boosts, and weird dudes trying to get into business with Tom’s old corn star neighbor. Buckle up, queef it up, and enjoy!
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#293 - "Dancers" Would Drop Me Off At School w/ That Mexican OT
Episode overview
This week on 2 Bears 1 Cave, Tom Segura and Bart Kersher are joined by rapper That Mexican OT! They kickoff the chat talking about Mexican food, burger spots, and That Mexican OT reveals
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This week on 2 Bears 1 Cave, Tom Segura and Bart Kersher are joined by rapper That Mexican OT! They kickoff the chat talking about Mexican food, burger spots, and That Mexican OT reveals a wild secret he has about eggs. On top of being super chill, That Mexican OT is a real authentic dude and he opens up about his very unique upbringing that helped shape who he is today. The trio discuss everything from hunting kangaroos to Japanese cholos, plus they also talk about bullfighting, gangster moms, pimp fathers, four wheelers, Project Recess! Grab some Por Osos and enjoy this episode!
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