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

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

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 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 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. - For simple, online access to personalized and affordable care for Hair Loss, ED, Weight Loss, and more, visit https://Hims.com/BEARS. - Upgrade your wardrobe and save on @trueclassic at https://trueclassic.com/BEARS! #trueclassicpod 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 Learn more about your ad choices. Visit megaphone.fm/adchoices

SPONSORS: - 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 - Upgrade to ShipStation today to get a sixty-day free trial at https://www.shipstation.com/cave. - If you’re 21+, try VIIA! For 15% off AND a free gift with your first order head to https://viia.co/BEARS and use code BEARS! #viiaparter In this episode of 2 Bears, 1 Cave, James Gunn joins Tom Segura to talk filmmaking and the state of the entertainment industry. Gunn opens up about directing Superman, the pressures behind it, and the relief of its success. He also discusses his role as co-head of DC Studios, building a decade-long DC universe, and the bold choice to reshoot five and a half episodes of Peacemaker with a new Vigilante. Tom and James bond over grounded storytelling, casting decisions, and the balance between comedy, superhero films, and CGI. They also touch on the return of comedies to theaters and how the industry continues to evolve. 2 Bears, 1 Cave Ep. 307 https://tomsegura.com/tour https://www.bertbertbert.com/tour https://store.ymhstudios.com Chapters 00:00:00 - Intro 00:00:45 - Peacemaker, El Tigre, & Grounded Aesthetics 00:08:24 - Big Screen Comedy 00:22:04 - Hitting The Creative Lottery With Superman 00:32:59 - The Writing Process & Juggling Big Budgets 00:41:16 - Special FX & Special Actors 00:47:57 - Batman 00:55:53 - Star Wars 01:00:12 - Guardians Of Fun 01:04:11 - Serious Filmmaking & "Ripley" 01:08:36 - Casting Highs & Lows Learn more about your ad choices. Visit megaphone.fm/adchoices

SPONSORS: - Head to https://acorns.com/BEARS or download the Acorns app to get started. - 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. - Order a bottle of Por Osos and some killer merch online https://drinkporosos.com Hey look, it's your favorite podcast hosts, Tom Segura and Bert Kreischer! This week in the cave Bert kicks things off with a brand-new joke he swears is the best thing he’s ever written, before diving into an emotional (and hilarious) story about his late bull mastiff, and the wild twist involving the family dog's long-lost sister. From there, the Bears riff on straight cat dads, Bert’s “sleep divorce,” VR porn addictions, childhood prank calls, and even the lost art of memorizing phone numbers. Bert even calls his dead grandma and chit chats with scam caller live on air. The episode only gets wilder as Tom and Bert review real OnlyFans submissions from fans, debate who should be the first official “2 Bears OF star,” and spiral into some truly insane pitches that only these two maniacs could come up with. Plus: speech impediments, Elmer Fudd racism, trolling stories, gambling breakdowns from NFL Week 1, and Bert trying to recruit Zac Efron into a shirtless golf fantasy with their new NIL athlete. This might just be the best episode of this show in a long ass time, don’t miss it. 2 Bears, 1 Cave Ep. 306 https://tomsegura.com/tour https://www.bertbertbert.com/tour https://store.ymhstudios.com Chapters 00:00:00 - Intro 00:01:41 - Dogs & Cats 00:08:59 - VR Corn 00:17:30 - Memorizing Geography 00:23:24 - Memorizing Phone Numbers 00:31:35 - Prank Calls 00:37:59 - We Got Some OF Prospects 00:49:50 - Speech Impediments 00:53:45 - NFL Week 1 Gambling 00:59:51 - Bert Wants To Adopt Athletes Learn more about your ad choices. Visit megaphone.fm/adchoices

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. - Don’t let financial opportunity slip through the cracks, get half off your first year with promo code BEARS at https://www.monarchmoney.com/bears - 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 at https://NetSuite.com/BEARS. 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! 2 Bears, 1 Cave Ep. 305 https://tomsegura.com/tour https://www.bertbertbert.com/tour https://store.ymhstudios.com Gambling problem? Call one eight hundred Gambler. In New York, call eight seven seven eight HOPENY or text HOPENY (four six seven three six nine). 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). Twenty-one plus age and eligibility varies by jurisdiction. Fees may apply in Illinois. Void in Ontario. Bonus bets expire seven days after issuance. See https://sportsbook.draftkings.com/promos. NFL Sunday Ticket offer for new subscribers only and auto-renews until cancelled. Digital games and commercial use excluded. Restrictions apply. Additional NFL Sunday Ticket terms at https://youtube.com/go/nflsundayticket/terms. Limited time offer. Chapters 00:00:00 - Intro 00:01:30 - Druski Doing White Face 00:10:54 - Streamers Ruined The Military 00:17:32 - Would You Die For Our Country? 00:26:25 - Kam Patterson 00:33:20 - Another Tour 00:38:25 - College Football Weekend 00:49:42 - Let's Become OF Boosters 00:59:17 - Bert's Fight With LeeAnn 01:05:28 - Wrap Up Learn more about your ad choices. Visit megaphone.fm/adchoices