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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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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 Sitcoms
00:54:39 - Stav & Chrissy's Movie Corner
01:00:47 - New Jurassic Park
01:05:01 - A Message From Tom Segura
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Aug 4
1 hr 11 min
Video

Check out our new summer merch at https://store.ymhstudios.com/
SPONSORS:
- 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
https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com
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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Jul 28
1 hr 10 min
Video

Check out our new summer merch at https://store.ymhstudios.com/
SPONSORS:
- Upgrade your wardrobe and save on @trueclassic at https://trueclassic.com/BEARS! #trueclassicpod
- Sign up for a $1 per month trial period at https://shopify.com/bears
- Sponsored by BetterHelp. Our listeners get 10% off their first month at https://betterhelp.com/bears
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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Jul 21
1 hr 14 min
Video

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- Start your free online visit today at https://Hims.com/BEARS.
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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
https://www.bertbertbert.com/tour
https://store.ymhstudios.com
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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Jul 14
1 hr 14 min
Video

SPONSORS:
- Order on DoorDash and save big during Summer of DashPass. Sign up today! DashPass benefits apply only to eligible orders. Terms apply.
- Sponsored by BetterHelp. Our listeners get 10% off their first month at https://betterhelp.com/bears
- 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.
- If your revenues are at least in the seven figures, download the free e-book “Navigating Global Trade: 3 Insights for Leaders” at https://NetSuite.com/BEARS
- Get a 60-day free trial at https://www.shipstation.com/cave Thanks to ShipStation for sponsoring the show!
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
00:16:45 - FaceTiming Chrissy D
00:20:16 - The Middle Class Of Comedy
00:33:09 - Bert Explains Global Politics
00:39:48 - Hot Air Balloons Are Sketch
00:49:29 - Crazy Plane Stories
01:00:17 - Helicopters
01:06:45 - Uber Driver Smackdown
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Jul 7
1 hr 11 min
Video

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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.
They spiral into career-ending scandals — Ray Rice, Aaron Hernandez, Mel Gibson, Michael Jackson, and Hitler — and debate whether being talented enough erases your crimes. Plus: the Oceangate sub disaster, a fisherman who supposedly ate his friend, and a fascinating discussion about racist costumes, slurs, and Bert turning purple in a sauna. Also: plutonium, bad names, the lady versions of both bears, and how throwing your wife through a window could be noble. Classic Bear chaos.
2 Bears, 1 Cave Ep. 295
https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com
Chapters
00:00:00 - Intro
00:00:58 - DMV Hotties & Beefing With Kids
00:10:07 - Women & Children First
00:17:53 - Shame, Mel Gibson, & Lance Armstrong
00:24:57 - Famous People Committing Crimes
00:35:32 - Would You Rather?
00:39:13 - War Documentaries
00:44:48 - Slurs In Other Languages
00:53:44 - Names & The Studio Beef
00:59:11 - Japan & Uranium
01:05:08 - Lady Bert
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Jun 30
1 hr 9 min
Video

Check out Jim's new special Unconceivable right now on YouTube! Watch is here: https://www.youtube.com/watch?v=rb05fiUz6cU
SPONSORS:
-Our listeners get 10% off their first month at https://betterhelp.com/bears
-Get up to $200 off Square hardware when you sign up at http://square.com/go/bears ! #squarepod
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!
2 Bears, 1 Cave Ep. 294
https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com
Chapters
00:00:00 - Intro
00:00:38 - It's Hitler Summer
00:05:41 - Comedy Special Edits, Self-Hatred, & Narcissists
00:16:41 - Embracing Shame
00:23:49 - Dopamine Release
00:30:01 - Orson Welles & William Shatner
00:38:27 - Favorite Interview Guests & JFK Conspiracies
00:43:50 - Epstein
00:50:10 - Bombing
00:56:30 - Headliners
01:02:27 - Patrice O'Neal
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Jun 23
1 hr 12 min
Video

SPONSORS:
- Your summer wardrobe awaits! Get 20% off @chubbies with the code cave at https://www.chubbiesshorts.com/cave #chubbiespod
- Sign up for a $1 per month trial period at https://shopify.com/bears.
- Order a bottle of Por Osos and some killer merch online https://drinkporosos.com
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!
2 Bears, 1 Cave Ep. 293
https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com
Chapters
00:00:00 - Intro
00:04:16 - Mexican Food, Burger Places, & Eggs
00:10:47 - Kangaroo Hunting, Collabs, & Project Recess
00:19:56 - Bullfighting & Strippers
00:25:57 - Mom Scents & Med Shit
00:34:30 - Going International
00:40:18 - Authenticity & Growing Up Young
00:46:30 - Four Wheelers & Cholo Culture
00:52:26 - It's Scary Underwater
01:00:25 - Tough Guys
01:07:19 - Album Drop, Movies, & Rap Music
01:15:38 - Vodka Endorsement
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Jun 16
1 hr 25 min
Video

SPONSORS:
- Upgrade your wardrobe and save on @trueclassic at https://trueclassic.com/BEARS ! #trueclassicpod
- Head to https://acorns.com/bears or download the Acorns app to get started.
- Get started at https://factormeals.com/bears50off and use code bears50off to get 50 percent off plus FREE shipping on your first box.
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!
2 Bears, 1 Cave Ep. 292
https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com
Chapters
00:00:00 - Intro
00:00:35 - Sharts & Babies
00:05:08 - Tom Cruise
00:13:42 - Dad Stuff
00:20:12 - COMEDY!
00:27:22 - Hate From The Internet
00:33:42 - New York Comedy Scene
00:38:46 - Gay For Bert
00:44:41 - Conquering New York
00:51:03 - Right Man For The Job
01:00:10 - Texas
01:03:34 - Wrap Up
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Jun 9
1 hr 6 min
Video

Check out the newest podcast from YMH Studios "Not A Damn Chance"! Hosted by pro skateboarder Neen Williams and Michelin-starred chef Phillip Frankland Lee https://www.youtube.com/watch?v=ihy5odp5G9A
SPONSORS:
- 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.
- If your revenues are at least in the seven figures, download the free e-book “Navigating Global Trade: 3 Insights for Leaders” at https://NetSuite.com/BEARS.
- Sponsored by BetterHelp. Our listeners get 10% off their first month at https://betterhelp.com/bears
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!
2 Bears, 1 Cave Ep. 291
https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com
Chapters
00:00:00 - Intro
00:02:36 - Chicago Shenanigans
00:16:06 - Mouth Stuff
00:19:39 - Bombing Hawaii
00:29:01 - Friends
00:36:51 - Internet
00:43:28 - Women
00:49:04 - Big Words
00:59:18 - Mandela Effects
01:03:51 - Kids Stuff With Big Cat
01:12:09 - Gambling
01:20:42 - MobLand
01:24:17 - Work From Home
01:30:37 - Big Cat's Other Interests
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Jun 2
1 hr 39 min
Video
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