2 Bears, 1 Cave with Tom Segura & Bert Kreischer

Available Episodes

5 of 318

My Dad Was Probably A Murderer w/ Kirk Fox | 2 Bears, 1 Cave
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
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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 . 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
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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 Learn more about your ad choices. Visit megaphone.fm/adchoices
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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 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
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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 Learn more about your ad choices. Visit megaphone.fm/adchoices
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