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