2 Bears, 1 Cave with Tom Segura & Bert Kreischer

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

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

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

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

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