Ep. 141 | 2 Bears 1 Cave w/ Tom Segura & Ryan Sickler

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 - Protect your family with life insurance from Ethos. Get your free quote at https://Ethos.com/BEARS - Head to https://DRINKAG1.com/BEARS you’ll get the welcome kit, a Morning Person hat, a bottle of Vitamin D3+K2, a AG1 Flavor Sampler and you’ll get to try their new sleep supplement AGZ for free. - Sign up for a $1 per month trial period at https://shopify.com/bears. 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! https://www.instagram.com/stavvybaby2 https://www.instagram.com/chrisdcomedy/ 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 - Intro 00:03:29 - Slutty Little Breakfast 00:07:14 - Podcast Polyamory 00:14:15 - Chrissy Housing Crisis 00:21:35 - Stavros Vs Fat Guy Medicine 00:31:48 - Fat Joe, Guy Code, & Graveyard Of Failed Shows 00:46:14 - Maybe The Worst Dog Ever 00:56:17 - Geopolitical Shenanigans & NYC Mayors 01:08:11 - Wrap Up Learn more about your ad choices. Visit megaphone.fm/adchoices

SPONSORS: - Make life easier by getting harder and discover your options at https://bluechew.com - If you’re 21 or older, get 25% OFF your first order + free shipping @IndaCloud with code BEARS at https://inda.shop/BEARS! #indacloudpod - For a limited time Hollow Socks is having a Buy 2, Get 2 Free Sale. Head to https://hollowsocks.com/ today to check out their huge sale. #HollowSockspod - Get 15% OFF your entire order with code BEARS at https://Manscaped.com. - Anyway, if you want to try Rho Nutrition’s NAD+, the Glutathione, whatever, they’re giving 20% off with the code BEARS at https://rhonutrition.com/discount/BEARS 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 Learn more about your ad choices. Visit megaphone.fm/adchoices

SPONSORS: - Go to https://HelloFresh.com/bears10fm now to Get 10 Free Meals + a Free breakfast for Life! - Make life easier by getting harder and discover your options at https://bluechew.com 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 Learn more about your ad choices. Visit megaphone.fm/adchoices

SPONSORS: - Protect your family with life insurance from Ethos. Get your free quote at https://ethos.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. - 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. - Sign up for a $1 per month trial period at https://shopify.com/bears. ‌ 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 https://tomsegura.com/tour https://www.bertbertbert.com/tour 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 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 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 - 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 Learn more about your ad choices. Visit megaphone.fm/adchoices

SPONSORS: - Sign up for a $1 per month trial period at https://shopify.com/bears - If you’re 21 or older, get 40% OFF your first order + free shipping @‌IndaCloud with code BEARS at https://inda.shop/BEARS ! #indacloudpod - Head to https://DRINKAG1.com/BEARS to get a FREE Welcome Kit with an AG1 Flavor Sampler and a bottle of Vitamin D3 plus K2, when you first subscribe! - Our listeners get 10% off their first month at https://betterhelp.com/bears ‌ 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 https://tomsegura.com/tour https://www.bertbertbert.com/tour https://store.ymhstudios.com 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 Learn more about your ad choices. Visit megaphone.fm/adchoices

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: -Take advantage of Ridge’s Biggest Sale of the Year and GET UP TO 47% Off  by going to https://www.Ridge.com/CAVE  #Ridgepod -Get $10 Off @‌BRUNT with code CAVE at https://www.bruntworkwear.com/CAVE  #BRUNTpod -Give the gift of smooth this holiday season with the Performance Package 5.0 Ultra. Get 15% off + free shipping at https://Manscaped.com with code BEARS. -Order a bottle of Por Osos and some killer merch online https://drinkporosos.com 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 https://tomsegura.com/tour https://www.bertbertbert.com/tour https://store.ymhstudios.com 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) Learn more about your ad choices. Visit megaphone.fm/adchoices

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 Learn more about your ad choices. Visit megaphone.fm/adchoices

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 https://tomsegura.com/tour https://www.bertbertbert.com/tour 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 Learn more about your ad choices. Visit megaphone.fm/adchoices

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 Learn more about your ad choices. Visit megaphone.fm/adchoices

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 your wallet today! Get 10% Off @Ridge with code CAVE at https://ridge.com/CAVE #ridgepod - Stop overpaying and start saving with Ownwell. Sign up in 3 minutes at https://Ownwell.com/bears - If you’re 21 or older, grab 30% off your first order plus free shipping with code BEARS at https://indacloud.co - 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. 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 Learn more about your ad choices. Visit megaphone.fm/adchoices