2 Bears, 1 Cave with Tom Segura & Bert Kreischer

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2 Bears, 1 Cave with Tom Segura & Bert Kreischer artwork
Comedy
Society & Culture

by YMH Studios

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.

12 episodes summarized

Episodes

Nick Kroll Convinced Netflix to Air Animated Animal Sex | 2 Bears, 1 Cave

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Gape your 4th eye with Kurt Metzger and Duncan Trussell's new podcast Mystery Boys and get to the bottom of what's really going on in the world: https://www.youtube.com/playlist?list=PL-i3EV1v5hLfZinN-4ZV4wmZ862wupBWF Also, check out Tom's new bakery, Ciccio Bomba, at the new third location at 1100 South Lamar Blvd in Austin, right across from the Alamo Drafthouse. SPONSORS: - Sign up now and Acorns will boost your new account with a $5 bonus investment. Join the over 14 million all-time customers who have already saved and invested over $27 billion dollars with Acorns. Head to acorns.com/bears or download the Acorns app to get started. - 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. - Don’t let your mind get in the way of a good time. Discover your options at https://BlueChew.com - Right now, Babbel is offering listeners up to 60% off. Go to https://Babbel.com/BEARS - Sponsored by Better Help. Sign up and get 10% off at https://betterhelp.com/bears - Sign up for your one-dollar-per-month trial and start selling today at https://shopify.com/bears This week on 2 Bears 1 Cave, Nick Kroll joins Tom and Bert to break down his new Netflix animated series Mating Season, why animation produces tighter comedy than anything shot on the fly, and the emotional formula behind Big Mouth that turned a filthy puberty show into something people actually shed real tears for. Along the way, they get into an all-timer story from a legendary comedy industry gathering featuring basically every comic you've ever loved, Tom's Charlie Murphy sushi dinner story, Bert's 50-pound weight loss and very specific relapse date, a true urban legend about Michael Landon and a javelin, a genuinely compelling movie pitch called The Quad Squad, and somehow end up in a deep dive on the Eichmann trial, featuring Sir Ben Kingsley showing up to a table read entirely off-book with a swastika-covered script. 2 Bears, 1 Cave Ep. 330 https://tomsegura.com/tour https://www.bertbertbert.com/tour https://store.ymhstudios.com Chapters 00:00:00 - Intro 00:06:30 - Why Animation Forces Comedians to Actually Write 00:18:31 - The Greatest Comedy Photo You're Not In 00:25:25 - Tom's Charlie Murphy Sushi Dinner Story 00:39:33 - Raccoons, Black Voice, & Building the Mating Season Universe 00:54:46 - Did Michael Landon Kill a Man With a Javelin? 01:01:18 - A Completely Serious Movie Pitch 01:04:19 - Clothes, Bert's Transformation, & Relapse Date 01:13:07 - Nacho Figueras & the Argentina Horse Riding Disaster 01:25:13 - Gay Moose, Goats, & Nick Kroll's Full Project Lineup 01:29:54 - N.O.R.E Calls In 01:32:30 - Nick Kroll Speaks Spanish 01:36:45 - Hunting Eichmann & Sir Ben Kingsley's Unhinged Table Read 01:44:11 - Wrap Learn more about your ad choices. Visit megaphone.fm/adchoices

June 1, 20261:45:14

Live from the Rose Bowl | 2 Bears 5K ft. Jelly Roll, Ari Shaffir, Joe DeRosa & Are You Garbage?

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The End is here! Ari's new storytelling show is $5.99 per episode at https://theend.ymhstudios.com. There's a total of 7 episodes for you to enjoy! Check out Joe DeRosa's new podcast Vile and Horrendous Pull up a chair and listen to what Joe does best: piss and moan! https://www.youtube.com/watch?v=bWvLI8xCAa0 Also, check out Tom's new bakery, Ciccio Bomba, at the new third location at 1100 South Lamar Blvd in Austin, right across from the Alamo Drafthouse. SPONSORS: - 🌎 Get an exclusive 15% discount on Saily data plans! Use code bears at checkout. Download Saily app or go to https://saily.com/bears ⛵ - Thanks to MANSCAPED for sponsoring today’s video! Get The Beard Hedger® Plus for 15% OFF + Free Shipping with code “BEARS” at https://Manscaped.com! - Sponsored by BetterHelp. Sign up and get 10% off at https://betterhelp.com/bears. - For simple, online access to personalized and affordable care for Hair Loss, Weight Loss, and more, visit https://Hims.com/BEARS. - Get sixty days free at https://ShipStation.com with code cave - For a limited time, our listeners get 50% off FOR LIFE, Free Shipping, AND 3 Free Gifts at Mars Men at https://Mengotomars.com Live from the legendary Rose Bowl during Netflix Is A Joke Fest, the Bears are back and even sweatier than usual! Tom Segura and Bert Kreischer take the stage fresh off the 2 Bears 5K for a completely unhinged live episode packed with race stories, weight loss victories, comic cameos, chaos, and pure degeneracy. Joined by Jelly Roll, Ari Shaffir, Joe DeRosa, and the guys from Are You Garbage?, the crew covers everything from losing hundreds of pounds and surviving airplane bathrooms while fat, to bidet discoveries, Netflix brunch disasters, H. Foley's iPhone nightmare, and the emotional insanity that surrounds the 2 Bears community. Plus: Bert reveals he mailed busts of his own dick to his closest friends, Tom bombs in front of Eddie Murphy and lives to tell the tale, Ari returns from traveling the world with a surprise award, and the whole crew spirals into stories about body transformations, sobriety, addiction, and comedy fame. 2 Bears, 1 Cave Ep. 329 https://tomsegura.com/tour https://www.bertbertbert.com/tour https://store.ymhstudios.com Chapters 00:00:00 - Intro 00:02:50 - Jelly Roll aka The Third Bear 00:23:40 - H. Foley & Kevin Ryan 00:49:51 - Ari Shaffir 01:03:38 - Joe DeRosa 01:12:56 - Wrap & Plugs Learn more about your ad choices. Visit megaphone.fm/adchoices

May 18, 20261:14:32

The Bears Go Up In Smoke | 2 Bears, 1 Cave

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The End is here! Ari's new storytelling show is $5.99 per episode at https://theend.ymhstudios.com. There's a total of 7 episodes for you to enjoy! Check out Joe DeRosa's new podcast Vile and Horrendous Pull up a chair and listen to what Joe does best: piss and moan! https://www.youtube.com/watch?v=bWvLI8xCAa0 SPONSORS: - Brought to you by BetterHelp. Sign up and get 10% off at https://betterhelp.com/bears. - Don’t let your mind get in the way of a good time. Discover your options at https://BlueChew.com - Get up to 60% off at https://Babbel.com/BEARS. - Sign up for your one-dollar-per-month trial and start selling today at https://shopify.com/bears - 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. - Head to https://acorns.com/bears or download the Acorns app to get started. This week on 2 Bears, 1 Cave, Tim and Bart go up in smoke, sharing cigars together as they talk about whatever floats around in their collective heads. They talk about fat guy problems, before going into Tiger Woods' spiraling personal life. The Bears also walk down memory lane, comparing the infamous fat Bert pitching photo to one of him recently, and the drastic change is pretty staggering. They also unpack the text exchange between a student and the teacher sister of influencer Noah Beck, share some wild drug stories, and check out a clip of Doug Stanhope roasting a city council. Also the 2 Bears 5k is coming up! Hope you been training. 2 Bears, 1 Cave Ep. 328 https://tomsegura.com/tour https://www.bertbertbert.com/tour https://store.ymhstudios.com Chapters 00:00:00 - Intro 00:01:56 - Fat Guy Problems 00:09:23 - Tiger Woods & Cigars 00:21:23 - Pitching Fat Pictures 00:29:30 - Noah Beck's Sister's Texts 00:43:40 - Age Differences 00:47:12 - Girl Talk 00:48:17 - Wild Drug Stories 00:59:19 - Doug Stanhope Fought City Hall 01:05:40 - Brendon Walsh Shenanigans 01:11:33 - Sabbatical & Wrap Up Learn more about your ad choices. Visit megaphone.fm/adchoices

May 4, 20261:16:23

The End Is Here w/ Ari Shaffir | 2 Bears, 1 Cave

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The End is Ari's new storytelling show! And it's finally here! Only at https://theend.ymhstudios.com/ . Get 7 full, hour long episodes of completely unfiltered stories for $29.99. Get it now! SPONSORS: - Go to https://ShipStation.com and use code cave for sixty days for free! - For simple, online access to personalized and affordable care for Hair Loss, Weight Loss, and more, visit https://Hims.com/BEARS. - Text BEARS to 64000 to get 20% off all IQBAR products, plus FREE shipping. Message and data rates may apply. - Get 15% OFF your entire order @‌MANSCAPED with promo code BEARS at https://manscaped.com! #ManscapedPartner #TCSociety - Brought to you by BetterHelp. When life feels overwhelming, therapy can help. Sign up and get 10% off at https://BetterHelp.com/bears. - Order a bottle of Por Osos and some killer merch online https://drinkporosos.com Welcome back to 2 Bears 1 Cave! This week, Tom Segura and Bert Kreischer are joined by the always unpredictable Ari Shaffir, dropping in to promote “The End”, a bold, no-holds-barred storytelling series that serves as a spiritual sequel and final evolution of his cult-favorite show This Is Not Happening.This episode dives deep into Ari’s return to long-form storytelling, breaking down how The End was independently produced with a stacked lineup featuring top-tier comics and a unique profit-sharing model that actually pays performers. The trio reflects on the evolution of comedy since Ari's original show, from Comedy Central’s heyday to today’s creator-driven landscape. The conversation spirals into outrageous personal stories, behind-the-scenes industry insights, and hilarious debates about everything from sobriety culture to the lost art of live storytelling. There’s also an unforgettable deep dive into a near-collaboration with Tracy Morgan, a story that almost made it into final show, and the unhinged unseriousness of morning show promotional interviews. Check out The End, y'all! We legit worked hard on it here at Studio Jeans. 2 Bears, 1 Cave Ep. 327 https://tomsegura.com/tour https://www.bertbertbert.com/tour https://store.ymhstudios.com Chapters 00:00:00 - Intro 00:01:37 - The End 00:04:13 - Big Dicks & Big Chicks 00:12:20 - The Missing Tracy Morgan Story 00:31:10 - Morning Show Chaos 00:43:47 - 2 Bears 5K 00:47:30 - Booze Tales & Sobriety Influencers 01:01:09 - Road Trip Stories 01:08:31 - Tito's Vodka & Final Thoughts Learn more about your ad choices. Visit megaphone.fm/adchoices

April 20, 20261:14:56

Somethings Burning And It's Bert's Bus | 2 Bears, 1 Cave

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The End is Ari's new storytelling show! It's almost here! Premieres April 16 on https://theend.ymhstudios.com/ . Presale pricing only available for a short time! You get 7 full, hour long episodes of completely unfiltered stories for $24.99. Afterwards, the price will increase so get it now! 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. - Get 10% off your first month of BlueChew Gold with code BEARS. https://bluechew.com - Sign up for your one-dollar-per-month trial and start selling today at https://shopify.com/bears - Brought to you by BetterHelp. When life feels overwhelming, therapy can help. Sign up and get 10% off at https://BetterHelp.com/bears. - Get up to 60% off at https://Babbel.com/BEARS. - Join the over 14 million all-time customers who have already saved and invested over $27 billion dollars with Acorns. Head to https://acorns.com/bears or download the Acorns app to get started. Bert Kreischer and Tom Segura are back with a wild new episode of 2 Bears, 1 Cave, and this one has everything: a terrifying tour bus fire, Bert’s ongoing recovery from blood clots, near-death anxiety, celebrity gossip, and a heated defense of napping. Bert breaks down the shocking story of how his bus blew a tire outside Fargo, was left behind overnight, and then burst into flames just hours later — a moment that may have saved everyone on board. He and Tom unpack how close the situation really was, what Bert lost in the fire, and why he’s still obsessing over the hats. The Bears also dive into Bert’s fear of flying, life on blood thinners, what it means to face mortality without booze, and the bizarre mental spiral that comes with multiple near-death experiences in a matter of months. From there, the conversation takes its usual chaotic turn into Club Shay Shay, the “lost everything and got it back” misunderstanding, the Jeffrey Epstein email chatter, Chappell Roan backlash, and whether Jon Bernthal is dead wrong about naps. They also talk about the upcoming 2 Bears 5K in Pasadena on May 9, Bert’s current fitness goals, and whether he can break 30 minutes in the race. 2 Bears, 1 Cave Ep. 326 https://tomsegura.com/tour https://www.bertbertbert.com/tour https://store.ymhstudios.com Chapters 00:00:00 - Intro 00:01:20 - Bert's Bus Burned Down 00:14:47 - Losing Everything 00:18:19 - A Really Cool Gift 00:20:40 - Death Is A Cruel Mistress 00:34:34 - Air Canada Accident + Other Aviation Disasters 00:43:10 - Chappell Roan 00:50:28 - Beefing With Jon Bernthal About Naps 00:56:34 - 2 Bears 5K 01:00:20 - New Bus & Doing Stand-Up Again 01:07:33 - Epstein, Fluffy, & KREISCHER Learn more about your ad choices. Visit megaphone.fm/adchoices

April 6, 20261:15:02

The Most Redacted Episode Ever | 2 Bears, 1 Cave

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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. - For simple, online access to personalized and affordable care for Hair Loss, Weight Loss, and more, visit https://Hims.com/BEARS. - Join the over 14 million all-time customers who have already saved and invested over $27 billion dollars with Acorns. Head to https://acorns.com/bears or download the Acorns app to get started. - Your emotional wellbeing matters. Find support and feel lighter in therapy. Sign up and get 10% off at https://BetterHelp.com/bears. - Learn a new Language and get up to 60% off your subscription at https://Babbel.com/BEARS - Sign up for your one-dollar-per-month trial and start selling today at https://shopify.com/bears In this episode of 2 Bears, 1 Cave, Bert Kreischer and Tom Segura cover everything from Bert’s sorta sober lifestyle, weight loss, sleep improvement, and 5K training to marriage non-negotiables, separate bedrooms, and life on tour. The Bears also react to internet beef between Quentin Tarantino and Rosanna Arquette, joke about the Epstein files, discuss "kept women", talk Trump and Mar-a-Lago, share a tense aborted plane landing story, and spiral into one of their darkest and funniest hypothetical conversations yet. If you missed this show, this one's for you. 2 Bears, 1 Cave Ep. 325 https://tomsegura.com/tour https://www.bertbertbert.com/tour https://store.ymhstudios.com Chapters 00:00:00 - Intro 00:01:19 - Bert's Weight Loss Journey 00:07:14 - Tarantino Beef & Unbothered Rogan 00:18:31 - Chef Drama 00:22:51 - Non-Negotiables 00:33:05 - Kept Women, Money, and Wild Relationship Logic 00:39:57 - Bert Learns He's In The Epstein Files 00:43:47 - Trump & Mar-A-Lago 00:50:07 - Dahmer & Plane Crashes 00:54:59 - How Would You Prefer To Die 01:02:23 - What Language Would You Prefer To Be Killed By? 01:06:55 - Racist Thing A Black Guy Told Me 01:11:40 - Vince Vaughan On The Pod? 01:13:35 - Wrap up Learn more about your ad choices. Visit megaphone.fm/adchoices

March 16, 20261:17:05

Bert's Not Dead | 2 Bears, 1 Cave

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SPONSORS: - Sponsored by Pepsi. Go try Pepsi Zero Sugar today. Let Your Taste Decide. - 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. - Get 10% off your first month of BlueChew Gold with code BEARS at https://bluechew.com - Sign up for your one-dollar-per-month trial and start selling today at https://shopify.com/bears - Sponsored by BetterHelp. BetterHelp makes it easy to get matched online with a qualified therapist. Sign up and get 10% off at https://BetterHelp.com/bears - Head to https://factormeals.com/bears50off and use code bears50off to get 50 percent off and free breakfast for a year. - Get up to 55% off at https://Babbel.com/BEARS. This week on Two Bears, One Cave, Tom Segura and Bert Kreischer spiral gloriously through brand loyalty, fast-food hot takes, donuts, Super Bowl commercials, health scares, and the kind of brutally honest conversations only best friends can have. The Bears break down why Pepsi Zero Sugar might actually be better than Coke Zero, debate McDonald’s fries vs. literally everyone else, and revisit classic brand wars like Burger King vs. McDonald’s and Dunkin’ vs. Krispy Kreme. From Blooming Onion horror stories to why you should never order seafood at a steakhouse, this episode is packed with food takes that will absolutely start arguments. Bert also opens up about his recent blood clot scare, panic attacks, medications, and how the experience completely shifted his perspective on health, mortality, and gratitude. The guys also talk sleep apnea machines, Benadryl addictions, Mounjaro side effects, testosterone confusion, and why medical advice somehow never agrees ever. Plus: donut shop conspiracies in Los Angeles, Cambodian vs. Vietnamese sandwich excellence, Krispy Kreme’s wild history, Instagram’s “fatties eating” algorithm, tracking down Ari Shaffir in the jungle, and why the 2 Bears 5K might literally save lives. 2 Bears, 1 Cave Ep. 324 https://tomsegura.com/tour https://www.bertbertbert.com/tour https://store.ymhstudios.com Chapters 00:00:00 - Intro 00:00:06 - Brand Wars 00:07:07 - Weight Loss Drugs 00:14:58 - Pepsi Challenge 00:22:40 - I Bought A Donut Shop 00:39:22 - Coin Pusher 00:40:54 - 2 Bears 5K Is Back! 00:45:13 - Bert's Blood Clot 00:49:38 - Where In The World Is Ari Shaffir? 00:54:39 - Black Appreciation 01:00:41 - Wrap Up Learn more about your ad choices. Visit megaphone.fm/adchoices

February 9, 20261:02:29

The End Of Humanity | 2 Bears, 1 Cave

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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 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. BetterHelp makes it easy to get matched online with a qualified therapist. Sign up and get 10% off at https://BetterHelp.com/bears - Sign up for your one-dollar-per-month trial and start selling today at https://shopify.com/bears The OG Bears are back on this absolutely unhinged episode of 2 Bears, 1 Cave! Bert Kreischer and Tom Segura dive headfirst into VR porn disasters, accidental virtual orgies, and the terrifying realization that Oculus might actually be ending humanity. Bert recounts a weekend alone that spirals into nine virtual orgies, soul-stealing eye contact, and panic-induced controller fumbling in a pitch-black room. The Bears also unpack loneliness, online hate comments, incel psychology, and how social media gives angry dudes a place to scream just to feel noticed. From there, things somehow get deeper: wealth guilt, excess consumption, purging hundreds of shoes and jackets, Mounjaro weight loss, beating Jelly Roll in the next 2 Bears 5K, parenting chaos, friendship evolution, Jake Paul as a “god,” and why success is always part luck. Enjoy the Bears while they're here. https://www.instagram.com/stavvybaby2 https://www.instagram.com/chrisdcomedy/ 2 Bears, 1 Cave Ep. 323 https://tomsegura.com/tour https://www.bertbertbert.com/tour https://store.ymhstudios.com Gambling Problem? Call 1-800-GAMBLER. New York: call 8778- HOPENY or text HOPENY. Connecticut: call 888-789-7777 or visit https://CCPG.org. On behalf of Boot Hill Casino in Kansas. Wager tax pass-through may apply in Illinois. Twenty one plus in most states. 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 00:00:14 - Bert's First Threesome 00:05:58 - Mean Comments 00:13:05 - Hanging With The Kids During Christmas 00:30:02 - Stroke Of Luck 00:34:11 - Excess & Purging Stuff 00:44:05 - Weight Loss, Mounjaro & Jelly Roll 00:55:15 - Jake Paul Is A God? 01:01:01 - Wrap Up Learn more about your ad choices. Visit megaphone.fm/adchoices

January 12, 20261:03:03

The Dark Side of Internet Fame w/ Marcus King | 2 Bears, 1 Cave

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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

December 1, 20251:28:06E317

My Dad Was Probably A Murderer w/ Kirk Fox | 2 Bears, 1 Cave

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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

November 17, 20251:09:07E315

Mel Robbins Calls Out Bert’s People-Pleasing | 2 Bears, 1 Cave

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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

November 10, 20251:59:04E314

Tom and Bert's Favorite OF Submissions | 2 Bears, 1 Cave

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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

October 6, 20251:04:58E309