2 Bears, 1 Cave with Tom Segura & Bert Kreischer

By YMH Studios

Weekly, comedian best friends Tom Segura and Bert Kreischer get together in the bear cave at YMH Studios to do what bears do: make each other laugh.... more

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FAQs about 2 Bears, 1 Cave with Tom Segura & Bert Kreischer:

How many episodes does 2 Bears, 1 Cave with Tom Segura & Bert Kreischer have?

The podcast currently has 327 episodes available.

2 Bears, 1 Cave with Tom Segura & Bert Kreischer episodes:

December 01, 2025 The Dark Side of Internet Fame w/ Marcus King | 2 Bears, 1 Cave
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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
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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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1h 29min
November 24, 2025 Louis C.K. on Writing His First Novel and Returning to Stage | 2 Bears, 1 Cave
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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.
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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Chapters
00:00:00 - Intro
00:01:00 - Becoming A Novelist, Eastern Europe, & Russian Literature
00:05:12 - Quitting Stand Up & Daily Rituals
00:08:47 - Writing Ingram & Why Tom Teared Up
00:19:38 - Loneliness, Street Kids, & the Human Threshold for Empathy
00:34:27 - Trauma, War & Emotional Damage
00:39:17 - Coming Back to Stand-Up & Rebuilding Material
00:46:22 - Upsetting Audiences, Articulating Thoughts, & Punching Down
00:59:59 - Touring Burnout & The Future of Live Comedy
01:06:42 - Final Thoughts & Tom Praises Ingram

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1h 9min
November 17, 2025 My Dad Was Probably A Murderer w/ Kirk Fox | 2 Bears, 1 Cave
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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.
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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1h 10min
November 10, 2025 Mel Robbins Calls Out Bert’s People-Pleasing | 2 Bears, 1 Cave
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 .
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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 Kidman Kiss & Approval Addiction
01:01:39 - ADHD, Dyslexia, & The Volcano Inside
01:10:44 - What Could Possibly Go Wrong?
01:20:01 - Bert Gets Real
01:31:05 - Wired To Change
01:36:25 - Opportunity Of A Lifetime
01:45:51 - Let Them (And Let Yourself)

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1h 60min
November 03, 2025 Duncan Trussell BLOWS Bert's Mind! | 2 Bears, 1 Cave
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.
SPONSORS:
- Protect your family with life insurance from Ethos. Get your free quote at https://Ethos.com/BEARS
- Get your first month of BlueChew FREE Just use promo code BEARS at checkout and pay five bucks for shipping https://bluechew.com
- Sponsored by BetterHelp. Our listeners get 10% off their first month at https://betterhelp.com/bears
- Right now, get our free business guide, Demystifying AI, at https://Netsuite.com/BEARS.
- 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. If you’ve ever wondered why we laugh at tragedy, why people live like they’re being filmed, or if you might just be an AI simulation of yourself — this is the episode for you.
2 Bears, 1 Cave Ep. 313
https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com
Chapters
00:00:00 - Intro
00:00:43 - Death Plans & Bigfoot’s Balls
00:03:59 - AI, Immortality & Roko’s Basilisk
00:07:02 - Main Character Syndrome
00:14:54 - Comedy, Therapy & Freddie Soto
00:17:10 - Hail Satan & The Disney Adult Disaster
00:22:46 - Loving Your Fans & Bert’s Cruise of Chaos
00:33:07 - Performative Life & The Polar Plunge Moment
00:41:50 - Are You Really You? Identity, Trauma, & Thumbnail People
00:54:17 - Smiling on the Way to the Gallows
01:03:10 - Cancel Culture, Bunkers & The Human Comedy
01:09:52 - The Weird Miracle Of Being Alive
01:13:43 - Bert Ruined A Photo Op

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1h 19min
October 27, 2025 The Undertaker Goes One-On-One With Tom Segura! | 2 Bears, 1 Cave
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.
SPONSORS:
- Get $10 Off at BRUNT with code CAVE at https://www.bruntworkwear.com/CAVE #bruntpod
- Eat smart at https://FactorMeals.com/bears50off and use code bears50off to get 50% off your first box, plus Free Breakfast for 1 Year.
- Order a bottle of Por Osos and some killer merch online https://drinkporosos.com
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 teammates during basketball drills to heartfelt reflections on the fans who grew up with him, The Deadman proves he’s every bit as thoughtful as he is intimidating.
2 Bears, 1 Cave Ep. 312
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https://store.ymhstudios.com
Chapters
00:00:00 - Intro
00:01:09 - Wrestlemania
00:06:36 - I Wanna Be A Wrestler
00:17:17 - The Birth Of The Undertaker
00:31:26 - Injuries & Finding New Roles
00:42:40 - Big Strong Guys
00:47:35 - Shawn Michaels
00:56:17 - Novices
00:59:54 - Stupid Purchases
01:03:25 - Mike Tyson
01:06:57 - Wrap Up

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1h 11min
October 20, 2025 Robert DeNiro Didn't Wanna Be Friends w/ Sebastian Maniscalco | 2 Bears, 1 Cave
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.
SPONSORS:
- Head to https://DRINKAG1.com/BEARS to get a FREE Welcome Kit, including a bottle of Vitamin D and free AG1 Travel Packs, when you first subscribe!
- 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.
- Sponsored by BetterHelp. Our listeners get 10% off their first month at https://betterhelp.com/bears
- Sign up for a $1 per month trial period at https://shopify.com/bears.
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
https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com
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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1h 25min
October 13, 2025 Why Ice Cube Stays Mad in Every Movie w/ Funny Marco | 2 Bears, 1 Cave
Attention Hanover, MD! Tommy Buns is coming to The Hall At Live! Casino, Sunday, October 19. Get tickets now at https://tomsegura.com/tour
SPONSORS:
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- If you’re 21 or older, grab 30% off your first order plus free shipping with code BEARS at https://indacloud.co
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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
https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com
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 apply in Illinois. Twenty-one plus age and eligibility varies by jurisdiction. Void in Ontario. 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 - Intro
00:02:17 - What's My Age Again?
00:14:14 - Interviewing Celebs & Getting A Lambo From Nicki Minaj
00:20:14 - Orlando Brown & Bert's Cabin
00:29:31 - Top Black Comedy Movies
00:40:40 - Fame
00:50:20 - Strip Clubs
00:55:55 - NBA YoungBoy
01:00:25 - The Art Of Not Giving A F
01:05:00 - Animation Domination
01:08:55 - Black Phrases
01:15:25 - Lying
01:19:46 - Chappelle, Kevin Hart, IShowSpeed, & Kai Cenat
01:28:12 - The Entertainment Of Watching People's Lives
01:36:42 - Closing Thoughts

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1h 42min
October 06, 2025 Tom and Bert's Favorite OF Submissions | 2 Bears, 1 Cave
Attention Hanover, MD! Tommy Buns is coming to The Hall At Live! Casino, Sunday, October 19. Get tickets now at https://tomsegura.com/tour
SPONSORS:
- As always, get your first month of BlueChew FREE Just use promo code BEARS at checkout and pay five bucks for shipping. https://bluechew.com
-Sponsored by BetterHelp. Our listeners get 10% off their first month at https://betterhelp.com/bears
- Download the CFO’s Guide to AI and Machine Learning for FREE at https://NetSuite.com/BEARS.
This week, Bert and Tom dive headfirst into the weirdest brain rot rabbit holes yet — from testing out VR porn ("you can see her fillings!") to auditioning more OnlyFans submissions, one of which that includes… a unique Por Osos bottle cameo. The Bears also pitch a business idea for a grown-man “locker room,” debate how Bert's woke daughters compare to Tom's redneck sons, and discover the world’s wildest dogs and cats. Plus: Jelly Roll’s 5K transformation, Savannah cats that look like mini-lions, and Bert’s desperate plan to sneak another puppy past Leanne.
It’s sex robots, freeze porn, fat-to-fit inspiration, and pet chaos all rolled into one classic 2 Bears, 1 Cave mess.
2 Bears, 1 Cave Ep. 309
https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com
Chapters
00:00:00 - Intro
00:03:22 - Jimmy Kimmel and Tylenol
00:08:17 - New Interest
00:15:54 - What The Kids Are Into
00:27:48 - The Bears Draft A Prospect
00:38:32 - The Locker Room Experience
00:46:18 - Jelly Roll
00:52:10 - Cane Corso vs. Dogo Argentino vs. Savannah Cat
01:01:14 - Wrap Up

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1h 5min
September 29, 2025 Phones Are Making You Unfunny w/ Jimmy Carr | 2 Bears, 1 Cave
Attention Hanover, MD! Tommy Buns is coming to The Hall At Live! Casino, Sunday, October 19. Get tickets now at https://tomsegura.com/tour
SPONSORS:
- Upgrade to ShipStation today to get a sixty-day free trial at https://www.shipstation.com/cave.
- 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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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
https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com
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 - The Privilege of Pressure & Boredom
00:43:36 - Beautiful People
00:53:56 - Boinking Bert
00:59:02 - James Bond & GTA 6
01:06:11 - Quentin Tarantino
01:12:47 - Wrap Up

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1h 17min

FAQs about 2 Bears, 1 Cave with Tom Segura & Bert Kreischer:

How many episodes does 2 Bears, 1 Cave with Tom Segura & Bert Kreischer have?

The podcast currently has 327 episodes available.

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