Season 2025 - Episode Guide

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 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, 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 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! 

It's another week of 2 Bears, 1 Cave with Tom Segura and Bert Kreischer!!! 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!

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. Check it out!

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!

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. 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!

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. Enjoy the show!

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 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. Enjoy the show!

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!

Tom and Bert are back in the cave and things get spicy fast. This week the Bears dive into alternative p*rn genres you didn't know you needed, celebrate the beauty of international women, and break down the logic and logistics behind the noble art of "homie head." They also mentally prepare for a Por Osos gay bar takeover and talk the top 5 hot chick accents. Next, Bert recounts his unforgettable Monday Night RAW moment where he went full low-IQ adult and choke slammed two dudes on live TV! Then it's onto arranged marriages, glory holes, and other socially important topics. Pack a towel, this one gets sweaty.

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!

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.

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.

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. Enjoy the show!

This week on 2 Bears 1 Cave, Tom Segura and Bert Kreischer go deep on Tom's new Netflix series Bad Thoughts — a disturbing, hilarious, and brilliantly unhinged ride that Charo absolutely hated. The Bears talk about favorite sketches, behind-the-scenes moments, bloopers, and why Bert is both joking and not joking about not being cast.

This week on 2 Bears 1 Cave, Bert is on a retreat in Istanbul so Tom Segura is joined by the brilliantly bizarre Harland Williams for an unhinged episode packed with supposedly true stories, bootyholes, and too many farts. Harland kicks things off by reminiscing about fingering calamari and the first time someone touched his arse—with a thermometer. Tom shares the traumatic moment he had to show a friend his infamously hairy sphincter... and yes, he ends up showing Harland too.

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. Enjoy the episode!

This week on 2 Bears 1 Cave, Tom Segura is joined by the hilariously unfiltered Mark Normand! 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! 
 

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!

This week on 2 Bears 1 Cave, Tom Segura is joined by the legendary Jim Norton! The bears dive into Jim's brand new special, why he no longer wants to be a cuck, and what it's like to live shamelessly — including some very NSFW stories from Brazil. Tom and Jim cover everything from a friendly Hitler and war documentaries to bombing onstage and the dark side of stand-up. They check out clips of Orson Welles' drunk ad reads and William Shatner being difficult during a recording, and discuss JFK conspiracies, before pivoting to the power of charismatic maniacs like Jeffrey Epstein. Plus, Tom confronts his own comedy insecurities and Jim shares some Patrice O'Neal stories and breaks down the wildest moments from his years in radio. You don't want to miss this one!

This week on 2 Bears 1 Cave, Tom checks in on Bert's intestine surgery and his new commitment to being loud, red, and barely alive. The Bears cover everything from Hellcats to Titanic cowards, and disgusting public behavior.

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.

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!

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).

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 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 forever? Stay tuned!

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. 
 

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."

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!

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! 

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!