• 1 hour 7 minutes
    Shane Gillis vs SNL: Round 2 | 2 Bears, 1 Cave

    SPONSORS:

    • Visit https://betterhelp.com/bears to get 10% off your first month.

    • Download the DraftKings Sports app and use code BEARS. New DraftKings customers can spend five and get two hundred in total bonuses paid within 21 days – includes all markets.

    • Get up to $200 off Square hardware when you sign up at https://square.com/go/bears! #squarepod

    • Get out there and enjoy the outdoors with Mountain Dew. An American Original. Tasting Great Since ’48. Look for Mountain Dew in stores near you.

    This week on 2 Bears, 1 Cave, Tom Segura and Bert Kreischer check in with Tom in Austin and Bert in New York for the Food & Wine Festival. Tom opens by tackling the Shane Gillis backlash from his SNL monologue, while Bert tries to stay out of it for once (he just really loves those pants). The Bears react to the livestreamed execution of the Fort Hood shooter getting called off. Then Bert declares himself Team Katie for new White House press secretary Katie Zacharia, from her shaky first briefing to her gym pics and the bar exam she failed, and the guys give her three months, tops. He also opens up about his people-pleasing after a woman on a plane Googles him and asks, "What did you do?" Plus: Condoleezza Rice's 9/11 story, Bert buying Napoleon's cologne in Paris, Pope Leo's surgery, a maintenance guy catching Bert's 54-year-old mirror selfie, Bert's street-interview do-over, Chris Distefano charming Rachael Ray on Something's Burning, and Mark Zuckerberg's first Guinness.


    2 Bears, 1 Cave Ep. 344


    https://tomsegura.com/tour

    https://www.bertbertbert.com/tour

    https://store.ymhstudios.com


    Gambling Problem? Call 1-800-426-2537, 1-800-697-3738. Connecticut: call 888-789-7777, visit https://ccpg.org/. On behalf of Boot Hill Casino in Kansas. Bet tax pass-through may apply in Illinois. 21+. Void in Canada. Event contract trading with DraftKings Predictions involves risk of loss. Availability varies. Predictions offer void in New York. Bet to get Bonus bets that expire in 7 days. Trade to get Predictions Dollars that expire in 1 year. $50 in rewards issued every 7 days via click to claim for 21 days. One non-withdrawable reward redeemable. Terms at https://dkng.co/audio. Limited time offer. Nationwide based on Sportsbook, Predictions, and Free-to-Play Sports Contest availability. Varies by State.

    Chapters

    00:00:00 - Intro

    00:00:58 - Shane Gillis' SNL Monologue

    00:06:28 - Bert Stays Quiet For Once & Those Gym Pants

    00:18:35 - The Fort Hood Shooter's Execution Gets Called Off

    00:23:15 - Katie Zacharia & Condoleezza Rice's 9/11 Story

    00:27:58 - The George Bushes & Napoleon's Cologne

    00:35:03 - The Press Secretary Failed The Bar & Bert's Oval Office Plan

    00:42:31 - "What Did You Do?" Bert Gets Googled On A Plan

    00:48:25 - Pope Leo, Bert's Mirror Selfie, & The Street Interview Do-Over

    00:56:50 - Chris Distefano Charms Rachael Ray

    01:01:30 - Zuckerberg's First Guinness & Wrap Up

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

    19 October 2026, 12:00 pm
  • 1 hour 10 minutes
    The Sebastian Maniscalco SiriusXM Drama | 2 Bears, 1 Cave | 2 Bears, 1 Cave

    SPONSORS:

    • If your revenues are at least in the seven figures, get our free business guide, Aligning for the Agentic Era: How AI Is Changing Everyday Work, at https://netsuite.com/BEARS.

    • Start your free online visit today at http://hims.com/bears for personalized care-from hair to ED to weight loss and more.

    • Thanks to MANSCAPED® for sponsoring today’s episode! Get The Lawn Mower® Ultra Gen 6 for 15% OFF + Free Shipping with code BEARS at https://Manscaped.com!

    • Sign up for your free Shopify trial at https://shopify.com/bears

    This week on 2 Bears, 1 Cave, Tom Segura and Bert Kreischer check in from the road, with Tom in Atlanta and Bert in Philly on his Permission to Party World Tour. The Bears debate whether they'll watch the Pentagon's livestreamed firing squad execution of the Fort Hood shooter, then dig into the SiriusXM Raw Dog Radio shakeup that had comics coming after Sebastian Maniscalco, and how one video turned into Bert starting a comedians union (Leanne is handling it). From there, Bert swears he'll die with his beard, finally tells Tom about the shot in Bad Thoughts season two he can't believe made the cut, and gets fired up over hood horse racing in Mississippi. Plus: Mike Ditka's one-take steakhouse commercial, Michael Jordan finding his lost championship rings in a forgotten safe, Chamillionaire's $25,000 autograph, Barry Sanders and The Fridge, and Tom getting pitched hair transplants.


    2 Bears, 1 Cave Ep. 343


    https://tomsegura.com/tour

    https://www.bertbertbert.com/tour

    https://store.ymhstudios.com

    Chapters

    00:00:00 - Intro

    00:06:15 - Should You Watch The Fort Hood Shooter's Execution?

    00:12:14 - Black Horse Racing & Sprinting On A Horse

    00:19:31 - Bert Will Die With This Beard & The Bad Thoughts Shot

    00:24:52 - SiriusXM, Raw Dog Radio, & The Sebastian Maniscalco Backlash

    00:35:19 - Bert's Comedians Union

    00:41:25 - Spam Calls & Mike Ditka's One-Take Commercial

    00:46:34 - Michael Jordan's Lost Championship Rings

    00:56:52 - Barry Sanders, The Fridge, & Elway's Two-Minute Drill

    01:03:07 - Tommy Time & Wrap Up

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

    12 October 2026, 12:00 pm
  • 1 hour 11 minutes
    The Most Delusional Man In Comedy | 2 Bears, 1 Cave

    SPONSORS:

    • Head to https://BlueChew.com and buy two months of BlueChew Gold you get the third FREE with 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. Trustpilot rating as of 6/1/2025.

    • This episode is sponsored by Betterhelp. Get 10% off your first month. Visit https://betterhelp.com/bears to explore your payment options.

    • Sign up for your free trial at https://shopify.com/bears

    • Sign up now and join over 14 million people already investing with Acorns. New customers get a $20 bonus investment just for signing up. Head to https://acorns.com/bears to claim your $20 bonus today. Limited time offer. Terms and conditions apply. See https://acorns.com/terms for details.

    This week on 2 Bears, 1 Cave, Tom Segura and Bert Kreischer call in from opposite ends of the map: Tom on a day off from his movie in Atlanta, Bert from Cleveland's Rocket Mortgage arena. Bert pulls up old Hollywood stars next to today's to prove Tom belongs in Cocoon, and Tom fires back that Bert looks like ten pounds of shit in a five-pound bag. Then Bert drags in an arena worker to vouch for his looks, and she guesses Tom is 45. From there, the Bears lock in a bench press push-up challenge, Bert asks Claude who he should support between Israel and Palestine, before he finally admits to needing a seatbelt extender. They also get into Zach Bryan's Free Palestine shirt at Gillette Stadium, Ari Emanuel's memoir Roll the Calls, Bert's brutal gum surgery, Tom Cruise's Digger, and Tom introducing Bert to the cinematic universe of Quan Millz.


    2 Bears, 1 Cave Ep. 342


    https://tomsegura.com/tour

    https://www.bertbertbert.com/tour

    https://store.ymhstudios.com

    Chapters

    00:00:00 - Intro

    00:04:09 - Football, The Metric System, & Catching Strays

    00:09:13 - Tom Belongs In Cocoon

    00:16:07 - One-Drink Bert & The Bench Press Push-Up Challenge

    00:28:11 - Club Runs, Zach Bryan, & The Pillow Debate

    00:33:20 - Goodwill Listening & The Gillette Stadium Beef

    00:37:15 - Bert Asks Claude To Pick A Side

    00:44:10 - "Do You Need Readers, Ma'am?"

    00:46:58 - Pretty Privilege & Bert's Seatbelt Extender

    00:50:31 - Ari Emanuel's Memoir & The Quan Millz Universe

    00:58:24 - Animating Bert's Dreams & Tom Cruise's Digger

    01:05:23 - Oppenheimer On A Phone & Wrap Up

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

    5 October 2026, 12:00 pm
  • 1 hour 52 minutes
    Tom Cruise Pulled His Own Tooth Out w/ Rob Lowe | 2 Bears, 1 Cave

    Presale tickets for Toms new tour Preposterous go live September 30th at 10am. Make sure to get yours over at https://tomsegura.com/tour and use code: TOMMY


    SPONSORS:

    • Head to https://superpower.com/bears for $50 off your membership. Get 150+ biomarkers tested every year plus a personalized health plan and on-demand care team. Detect early signs of 1,000+ conditions. #superpowerpod

    • Start learning a new language TODAY with Babbel. Right now listeners can save up to 60% off at https://Babbel.com/BEARS.

    • Get out there and enjoy the outdoors with Mountain Dew. An American Original. Tasting Great Since ’48. Look for Mountain Dew in stores near you.

    • If your revenues are at least in the seven figures, get our free business guide, Aligning for the Agentic Era: How AI Is Changing Everyday Work, at https://netsuite.com/BEARS .

    • Get started with ShipStation today and get sixty days free at https://ShipStation.com, with code cave.

    This week, Tom is off somewhere, so Bert Kreischer is joined by the legendary Rob Lowe, back in the Cave to talk about his new movie The Musical, the Sundance comedy with a twist so audacious the big distributors were too scared to buy it, now playing in theaters. Rob breaks down the 18-day shoot, the moment that makes audiences gasp, and why a small theatrical run still beats a mystery streaming "hit." From there, the two get into learning stick on La Cienega, LeeAnn's endless story recaps, Tom Cruise pulling his own tooth for The Outsiders, and Paul Newman's legendary hangs. Bert opens up about his Free Bert season two meltdown and the night he forgot how to yawn, Rob shares what 36 years of sobriety taught him, and they pitch the ultimate Netflix show: 24 Hours with Rob & Bert, starring Mark Wahlberg as Dirk Diggler. Plus: Usher's house tour, Bryson DeChambeau's eagle, and the national anthem bit.


    2 Bears, 1 Cave Ep. 341


    https://tomsegura.com/tour

    https://www.bertbertbert.com/tour

    https://store.ymhstudios.com

    Chapters

    00:00:00 - Intro

    00:00:39 - Skinny Bert & Driving Stick On La Cienega

    00:10:43 - Bert Doesn't Listen & The Cousin Who Can't Eat Anything With A Hoof

    00:23:54 - Tom Cruise Pulled His Own Tooth & Butch Cassidy Cool

    00:32:05 - The Musical & The Twist Nobody Would Buy

    00:48:40 - The Night Bert Couldn't Yawn

    00:54:54 - Measured Drinking & Rob's 36 Years Sobriety

    01:00:37 - Paul Newman

    01:05:43 - Rob's Headshot Composites & Growing Up Before Phones

    01:11:15 - Timothée Chalamet, Press Tours, & Tom Cruise's Perfect Day

    01:20:22 - Mark Wahlberg's 4AM Club & Bryson DeChambeau's Eagle

    01:32:11 - Stunt Flying With Tom Cruise & & The National Anthem Bit

    01:41:58 - Humble Sons & Usher's Netflix House Tour

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

    28 September 2026, 12:00 pm
  • 1 hour 13 minutes
    Raygun Deserved The Gold Medal | 2 Bears, 1 Cave

    SPONSORS:

    • New DraftKings customers, sign up with code BEARS, spend five bucks to get $150 in rewards within 14 days - includes all markets.

    • Get your free quote at https://ethos.com/BEARS.

    • Let’s eat real. Head to https://factormeals.com/bears50off and use code bears50off to get 50 percent off and 1 free breakfast item per box for 1 year, while supplies last until 10/31/2026. See website for more details.

    • Sign up and get 10% off at https://BetterHelp.com/bears. 

    • Start learning a new language TODAY with Babbel. Right now listeners can save up to 60% off at https://babbel.com/BEARS.

    • Get out there and enjoy the outdoors with Mountain Dew. An American Original. Tasting Great Since ’48. Look for Mountain Dew in stores near you.

    This week on 2 Bears, 1 Cave, Tom Segura and Bert Kreischer are on separate sides of the country, but still together in our hearts. Tom's about to film a movie and Bert's been running his takes through ChatGPT before he says them out loud, which still doesn't stop LeeAnn and his daughters from destroying him over The Pastor's Wife. Bert explains how Last Comic Standing edited him into the villain, and how much public misrepresentation a person should take before they swing back; Michael Jackson, Shane Gillis, Johnny Depp, Joe Rogan, and Bert's "how many bees until you start swatting" theory. From there, Bert delivers the two greatest analogies of his life, Tom demands the production Bible for Tenet to understand it better, and Bert turns his garage door into a guillotine. They also get into Kyle Forgeard of Nelk Boys running seven marathons in seven days, Bert's daughters hijacking his couples therapy to tell the therapist he only feels emasculated at Lowe's, and Bert's case that Raygun should have won the gold medal and that Jackson Pollock was a shill.


    2 Bears, 1 Cave Ep. 340


    https://tomsegura.com/tour

    https://www.bertbertbert.com/tour

    https://store.ymhstudios.com


    Gambling Problem? Call 1-800-426-2537, 1-800-697-3738. Connecticut: call 888-789-7777, visit http://ccpg.org. On behalf of Boot Hill Casino in Kansas. Bet tax pass-through may apply in Illinois. 21+. Void in Canada. Event contract trading with DraftKings Predictions involves risk of loss. Availability varies. Predictions offer void in New York. Bet to get Bonus bets that expire in 7 days. Trade to get Predictions Dollars that expire in 1 year. $50 in rewards issued every 7 days via click to claim for 14 days. One non-withdrawable reward redeemable. Terms at http://dkng.co/offer. Limited time offer. Nationwide based on Sportsbook, Predictions, and Free-to-Play Sports Contest availability. Varies by State.

    Chapters

    00:00:00 - Intro

    00:00:38 - ChatGPT Approved Takes & Death Of The Pastor's Wife

    00:07:17 - How Many Bees Until You Start Swatting? + Purple Doritos

    00:15:02 - Tom's Movie Beard & Revisiting Tenet

    00:28:44 - 365 One-Minute Episodes & Bryson DeChambeau's Hole In One

    00:34:08 - Mountain Dew Sizzle

    00:38:01 - Football Segue

    00:39:19 - Kyle Forgeard's Seven Marathons & Andrew Schulz's Miami Era

    00:43:50 - Bert's Tom Impression & Couples Therapy With The Girls

    00:51:03 - The Honey Deuce & Bert's Return To Drinking

    00:56:16 - What Olympic Sport Could You Actually Get Good At?

    01:02:50 - Raygun Deserved The Gold & Jackson Pollock Was A Shill

    01:12:15 - Wrap Up

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

    21 September 2026, 12:00 pm
  • 1 hour 12 minutes
    What Percent Gay Are You? | 2 Bears, 1 Cave

    Check out Hoop and Huddle, YMH Studios' new comedy sports show, hosted by comedians Luke Touma & Nate Marshall. Two friends talking basketball, football, and whatever ruined their weekend. Less "analysts breaks down the tape," more "your boys yelling at the TV." https://www.youtube.com/@UCdaQbXFKAuvKcZcwieo8A6A

    SPONSORS:

    • Thanks to MANSCAPED® for sponsoring today’s episode! Get The Lawn Mower® Ultra Gen 6 for 15% OFF + Free Shipping with code BEARS at https://Manscaped.com!

    • The DraftKings Sports app is now live in all 50 states! Head to https://dkng.co/bears

    • For simple, online access to personalized and affordable care for Hair Loss, Weight Loss, and more, visit https://hims.com/bears

    • Sign up and get 10% off at https://BetterHelp.com/bears.

    • Get out there and enjoy the outdoors with Mountain Dew. An American Original. Tasting Great Since ’48. Look for Mountain Dew in stores near you.

    Welcome back to the cave! Hunter Biden says he's 48% gay, which raises the only question that matters: what percent are you? Bert and Tom build the math from zero, clothes, dicks, physiques, saunas, eye patches, a $5,000 face laser, and Bert climbs a lot higher than he expected to.

    Along the way: why Bert can't watch Sophie Cunningham highlights, the uncomfortable truth about loving Jason Williams, John Stockton's total lack of pizzazz, the hunt for a white DB in the NFL, Bert calling his dad mid-episode to check the family for slave owners (Tom's family does not come out clean), Bert's sister telling him to grow up about his sleep anxiety, Ila volunteering to fight Tom's ten-year-old in the Octagon, the 2:30am Dodger Stadium aftermath, a device that grades your poop, and Bert's full-throated defense of the Philadelphia Eagles' male cheerleader.

    Plus: this week's Mountain Dew summer sizzle submissions, including one that requires $2.6 million of CGI and one that just shuts Bert up.


    2 Bears, 1 Cave Ep. 339


    https://tomsegura.com/tour

    https://www.bertbertbert.com/tour

    https://store.ymhstudios.com


    In Partnership with DraftKings. The Crown Is Yours. Bet with DK Sportsbook: Gambling Problem? Call 1-800-426-2537, 1-800-697-3738. Connecticut: call 888-789-7777, visit https://ccpg.org. On behalf of Boot Hill Casino in Kansas. Bet tax pass-through may apply in Illinois. 21+. Void in Canada. Event contract trading with DraftKings Predictions involves risk of loss. Availability varies. Bet to get Bonus bets that expire in 7 days. Trade to get $50 in Predictions Dollars that expire in 1 year, issued every 7 days via click to claim for 21 days. 1 non-withdrawable reward redeemable. Predictions offer void in New York. Ends July 19th. Terms at https://dkng.co/audio.

    Chapters

    00:00:00 - Intro

    00:00:14 - Hunter Biden Says He's 48% Gay

    00:06:23 - Clip Farms, Sophie Cunningham, & Jason Williams

    00:15:32 - John Stockton, White Boxers & Tim Dwight

    00:29:23 - California's Slavery Bill & Bert Calls His Dad

    00:34:41 - The Girlfriend, The Sister, & The Fight Challenge

    00:42:34 - The Dodgers Game Aftermath & A Whoop For Your Toilet

    00:46:11 - Male Cheerleaders, Female Urologists, & Checking Out Men

    00:52:38 - Hiding From Lightning With A Grindr Meetup

    00:59:05 - Comedian OnlyFans & Ohtani's $17 Million Translator

    01:05:44 - Mountain Dew Summer Sizzle Submissions

    01:11:34 - Wrap Up

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

    14 September 2026, 12:00 pm
  • 1 hour 14 minutes
    Jelly Roll Called The President A Fat Pig | 2 Bears, 1 Cave

    SPONSORS:

    • Don’t let your mind get in the way of a good time. Discover your options at https://BlueChew.com

    • Visit https://ethos.com/BEARS

    • Sign up for your free trial at https://shopify.com/bears

    • Sign up now and join over 14 million people already investing with Acorns. New customers get a $20 bonus investment just for signing up. Head to https://acorns.com/bears to claim your $20 bonus today. Limited time offer. Terms and conditions apply. See https://acorns.com/terms for details.

    • New DraftKings customers, sign up with code BEARS spend five bucks to get $200 in rewards within 21 days - includes all markets.

    Welcome back to 2 Bears 1 Cave! This week Tom Segura and Bert Kreischer dive right in with Jelly Roll's headline-grabbing Kimmel monologue where he addressed the president as "from one fat pig to another." Bert then takes full credit for Jelly Roll's weight loss and the entire genesis of the Two Bears 5K, because technically he was in the room when that casually became a thing. They also have exciting news, a new 5K is coming in April and it's going to be bigger than ever.

    From there, Bert opens up about the panic attacks he's been having, severe, physical, and rooted in something he now understands: a complete lack of childhood bedtime structure. Tom grew up getting nightly Catholic prayers, a sign of the cross from mom, and the full rosary in the car for any trip over ten minutes. Bert grew up watching Letterman alone at nine years old at 3am while his dad slept off a ten mile run. The bears compare notes on childhood bedtime routines, how they each put their own kids down now, and what sleep anxiety looks like when it hits a grown adult, including Bert's most recent 36-hour panic attack that started when a friend told him he yawns too much and he forgot how to do it. He couldn't yawn for a day and a half. He finally yawned in couples therapy. That's where we are.

    They also get into Mel Gibson getting lightly canceled for mocking a sign language interpreter (on the scale of Mel Gibson incidents, this doesn't even register), a game of complimenting Salma Hayek on the one thing she's never heard in her 60 years on earth, Tom Hardy's new rap album, Jonah Hill's white belt jiu jitsu bravado and whether he'd actually beat Jason Bateman's ass, the Eddie Bravo black eye that made Bert walk out of a jiu jitsu class without ever taking his jeans off, and the Times Square Stabber whose fat padding made every taser completely ineffective and whose stabbing motion made this incident appear beyond ridiculous at first.


    2 Bears, 1 Cave Ep. 338


    https://tomsegura.com/tour

    https://www.bertbertbert.com/tour

    https://store.ymhstudios.com


    Gambling Problem? Call 1-800-426-2537, 1-800-697-3738. Connecticut: call 888-789-7777, visit https://CCPG.org. On behalf of Boot Hill Casino in Kansas. Bet tax pass-through may apply in Illinois. Twenty one plus. Void in Canada. Bet with DraftKings Sportsbook to get Bonus bets that expire in seven days OR Trade with DraftKings Predictions to get Predictions Dollars that expire in one year. Event contract trading involves risk of loss. Predictions offer void in New York. Non-withdrawable Rewards issued as Fifty dollar click-to-claims every seven days for twenty-one days. Terms at https://dkng.co/offer. Limited time offer. Nationwide based on Sportsbook, Predictions, and Free-to-Play Sports Contest availability. Varies by State.

    Chapters

    00:00:00 - Intro

    00:00:18 - Jelly Roll Called Trump A Fat Pig on Kimmel

    00:15:49 - Mel Gibson's Sign Language Incident & Cancel Culture

    00:22:32 - Childhood Bedtimes & Panic Attacks

    00:33:38 - Putting Kids to Bed & Bert's Sleep Anxiety Deep Dive

    00:41:44 - Bert Forgot How to Yawn and Had a 36-Hour Panic Attack

    00:51:25 - Salma Hayek At 60

    00:55:47 - Tom Hardy's Album, Shapeshifters & Jonah Hill's White Belt Energy

    01:05:56 - The Times Square Waddling Stabber

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

    7 September 2026, 12:00 pm
  • 1 hour 46 minutes
    Breaking Down The Barstool Brawl | 2 Bears, 1 Cave

    SPONSORS:

    Tom Segura and Bert Kreischer are back in the cave and surprise surprise, Bert opens with a confession: he wishes he'd never quit drinking. What follows is a full inventory of the modern male brain, the online pastor Tom watches every morning to get inspired, why 17-year-olds have no business being nostalgic for anything, the exact moment each of them gave up on playing pro sports, and why comedians never seem to get that same reality check. The guys break down Bert's Whoop addiction and the blood clot that started it, get talked into a completely fictional performance-enhancing stack for a 5K, fall in love with bull riding legend JB Mauney, pitch the worst sponsorship idea in podcast history, and watch a food delivery driver take on the entire Barstool office. Then it's cringe cancellation, sobriety influencers, 4:23 a.m. morning routine guys, and a long, very funny argument about which movie stars are actually men and which ones just look at themselves in the mirror. Plus Bert's new fragrance obsession, the colognes of Napoleon, Elvis and JFK, Sebastian Maniscalco's four seasonal robes, Joe Rogan's splits, Billy Bob Thornton at the CMAs, and a big announcement about the future of the show.


    2 Bears, 1 Cave Ep. 337


    https://tomsegura.com/tour

    https://www.bertbertbert.com/tour

    https://store.ymhstudios.com


    Bet with DK Sportsbook: Gambling Problem? Call 1-800-GAMBLER, 1-800-MYRESET. Connecticut: call 888-789-7777, visit https://CCPG.org. On behalf of Boot Hill Casino in Kansas. Bet tax pass-through may apply in Illinois. 21+. Void in Canada. Event contract trading with DraftKings Predictions involves risk of loss. Availability varies. Predictions offer void in New York. Bet to get Bonus bets that expire in seven days. Trade to get Predictions Dollars that expire in one year. $50 in rewards issued every seven days via click to claim for twenty-one days. One non-withdrawable reward redeemable. Terms at https://dkng.co/offer. Limited time offer. Nationwide based on Sportsbook, Predictions, and Free-to-Play Sports Contest availability. Varies by State.

    Chapters

    00:00:00 - Intro

    00:00:17 - The Jewish Joke Bert Can't Tell On Stage

    00:04:26 - Pastor Manning

    00:09:09 - Period Sex Confessions & Giving Up On Sports

    00:21:50 - Nobody Quits Comedy Or Drinking

    00:31:31 - Whoop Obsession, The Blood Clot, & Tren

    00:37:09 - JB Mauney & The PBR

    00:44:27 - Motorcycles & The 12 O'clock Boys Sponsorship

    00:46:56 - The Barstool Helmet Fight

    00:52:58 - Fighting Women

    00:56:13 - Cringe Cancellation

    01:01:35 - Tom's Pep Talk & Bert's Therapy

    01:05:05 - Sobriety Influencers & Morning Routine Guys

    01:09:04 - Cringey Actors vs. Real Men

    01:19:33 - Bert's Fragrance Obsession

    01:30:00 - Drakkar Noir Nostalgia

    01:36:49 - Sebastian Maniscalco Is A Study

    01:40:04 - Bert Meets Billy Bob At The CMAs

    01:44:26 - 2 Bears Is Going Back To Weekly

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

    31 August 2026, 12:00 pm
  • 1 hour 25 minutes
    Stavvy Called Us Out | 2 Bears, 1 Cave

    SPONSORS:

    This week on 2 Bears, 1 Cave, Tom Segura and Bert Kreischer celebrate Bert officially entering the Guinness Book of World Records for The Machine, possibly the most performed signature story in comedy history, and immediately spiral into the comedy record arms race: Shane Gillis' 77,000-person show, Nate Bargatze's 2 million tickets, the Dane Cook vs. Dave Chappelle longest-set war, and Bert's plan to lock 75,000 paid "hostages" inside Raymond James Stadium and perform for ten straight hours. Then the Bears respond to Stavros Halkias calling out comics who fly private, and explain why he's absolutely right: nobody gets funnier on a private jet. From there, Bert declares Busboys, the new Theo Von and David Spade movie, the greatest piece of art he's ever seen, and Tom finally watches The Odyssey, only for Bert to officially turn on it over the Travis Scott cameo. Plus: Gaddafi's all-female Amazonian Guard, plane-crash hypotheticals, Chimp Empire is the best reality show ever made, Mick Jagger on fame, and why the Bears are grateful they got famous late.


    2 Bears, 1 Cave Ep. 336


    https://tomsegura.com/tour

    https://www.bertbertbert.com/tour

    https://store.ymhstudios.com

    Chapters

    00:00:00 - Intro

    00:00:18 - Comedians Getting Guinness Records

    00:07:24 - The Attendance Record Arms Race

    00:18:09 - Stavvy Says Private Jets Don't Make You Funnier

    00:24:25 - Lunch Pail Phonies & Staying Honest

    00:35:39 - Busboys Is A Secret Masterpiece

    00:41:55 - Tom Finally Saw The Odyssey

    01:03:45 - Por Osos At Frenchies & MacDill

    01:07:29 - The Sexiest Military & Plane Crash Hypotheticals

    01:12:08 - Chimp Empire

    01:15:26 - Leanne's Birthday & The Black Crowes

    01:20:28 - Mick Jagger On Fame

    01:24:18 - Wrap Up

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

    24 August 2026, 12:00 pm
  • 1 hour 1 minute
    Tom & Bert's Brutally Honest Odyssey Review | 2 Bears, 1 Cave

    SPONSORS:

    • Don’t let your mind get in the way of a good time. Discover your options at https://BlueChew.com

    • Shopify: Turns out you don’t need a real job. Build your own business with a free trial
      at http://shopify.com/bears

    • Head to https://acorns.com/bears or download the Acorns app to get started.

    • New DraftKings customers, sign up with code BEARS spend five bucks to get one hundred fifty in rewards within 14 days, includes all markets. Over at https://dkng.co/bears.

    • For a limited time, our listeners get 50% off FOR LIFE, Free Shipping, AND 3 Free Gifts at Mars Men at http://Mengotomars.com.

    This week on 2 Bears, 1 Cave, Tom Segura and Bert Kreischer are back in the cave after eight weeks apart, and they open with a full review of The Odyssey, Lupita Nyong'o as Helen of Troy, Matt Damon's rogue Boston accent, and why Jon Bernthal is Hollywood's most legendary napper. From there, Bert unveils his billionaire rebrand (Sabah shoes, LBJ Stetsons, and the top five shoes billionaires wear this fall) before getting real about sobriety, anxiety attacks, and self-diagnosing 12 terminal illnesses in a single month. The Bears also spiral into the movies that blindsided them, Primal Fear, The Sixth Sense, Memento, Fight Club, and why the DIY hits like Obsession prove Hollywood is in another pivot moment. Plus: Project Hail Mary vs. the 15-hour audiobook, Bert's theory that this is the funniest (and most jacked) generation of comics ever, college football weight-room PRs, Jason Kelce showing up for a 9 AM bench session, and a meet & greet at MacDill Air Force Base August 14. If you missed the Bears, this one's for you.


    2 Bears, 1 Cave Ep. 335


    https://tomsegura.com/tour

    https://www.bertbertbert.com/tour

    https://store.ymhstudios.com

    Bet with DK Sportsbook: Gambling Problem? Call 1-800 GAMBLER, 1-800 MY RESET. Connecticut: call 888-789-7777, visit http://CCPG.org. On behalf of Boot Hill Casino in Kansas. Bet tax pass-through may apply in Illinois. Twenty one plus. Void in Canada. Event contract trading with DraftKings Predictions involves risk of loss. Availability varies. Predictions offer void in New York. Bet to get Bonus bets that expire in seven days. Trade to get Predictions Dollars that expire in one year. Fifty dollars in rewards issued every seven days via click to claim for fourteen days. One non-withdrawable reward redeemable. Nationwide based on Sportsbook, Predictions, and Free-to-Play Sports Contest availability. Varies by State. Terms at http://dkng.co/offer. Limited time offer. Chapters

    00:00:00 - Intro

    00:00:26 - The Bears Review The Odyssey

    00:10:34 - Bears At MacDill Air Force Base

    00:11:15 - Project Hail Mary & Bert's Cute Shoes

    00:23:37 - Bert's Drinking Again

    00:33:36 - Obsession & The New Hollywood Pivot

    00:39:00 - The Best Twist Movies Ever

    00:52:33 - Everyone's Got Abs

    00:56:02 - College Weight Room Energy

    01:00:44 - Wrap Up

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

    10 August 2026, 12:00 pm
  • 1 hour 3 minutes
    Fat Tommy Vs Skinny Tom | 2 Bears, 1 Cave

    SPONSORS:

    This week on 2 Bears, 1 Cave, Tom Segura and Bert Kreischer compare their two very different eras of being fat, Tom's custom-made fat guy shirts, hard visceral fat vs. soft fat, and why losing weight made everyone think Tom got lip injections. Bert's sober documentary binge takes them from Patient Zero "Gay Tom" spreading AIDS across the Air Canada route map to Concorde pricing scams. Tom also reveals the fattest thing he's ever seen Bert do: ten appetizers, four entrées, and twenty doubles in Tallahassee. Bert also retells Bill Hader's retelling of Henry Rollins meeting David Lee Roth, and his daughter's instantly legendary Boston Tea Party take. Then things get real: a midlife crisis YouTube video sends Bert and LeeAnn into a "sell everything and get five apartments in five cities" fantasy, LeeAnn gets brutally honest about when she was happiest, and Tom breaks down the difference between happy and content. Plus: Hulk Hogan inflating Andre the Giant's weight, Julian's belt reaction to the Michael Jackson movie, Whoop resting heart rate brags, Craig Robinson's dunk, and the great first sweat vs. last sweat debate.

    2 Bears, 1 Cave Ep. 334

    https://tomsegura.com/tour
    https://www.bertbertbert.com/tour
    https://store.ymhstudios.com

    Chapters
    00:00:00 - Intro
    00:00:52 - Fat Tommy Vs Skinny Tom
    00:09:16 - Patient Zero, Polio, & The Concorde
    00:19:38 - The Fattest Thing Tom Ever Saw Bert Do
    00:23:55 - Bill Hader, David Lee Roth & Boston Tea Party
    00:32:21 - Hulk Hogan, Macho Man & LeeAnn Off Leash
    00:36:37 - Five Apartments In Five Cities
    00:46:12 - Bert's Midlife Crisis Theory
    00:54:34 - "You're Not Hitting The Notes, Mike"
    00:57:05 - Whoop Brags & Craig Robinson Dunking
    01:02:36 - Wrap Up

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

    27 July 2026, 12:00 pm
  • More Episodes? Get the App