The Undertaker Goes One-On-One With Tom Segura! 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 SPONSORS: - Get $10 Off at BRUNT with code CAVE at - Eat smart at 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 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 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

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The Undertaker Goes One-On-One With Tom Segura! 2 Bears, 1 Cave is an episode from 2 Bears 1 Cave with Tom Segura & Bert Kreischer by 2 Bears 1 Cave.

This episode is 70:58 long.

This episode was published on Oct 27, 2025.

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