Transcript

A (0:00)

Hey, everyone. I'm filming my new stand up special in Milwaukee at the Riverside Theater on November 14th and 15th. Tickets are available in Milwaukee for the November 14th show only. Get your tickets now at TomSecura.com tour 100%.

B (0:16)

Cheers. All right.

A (0:20)

Welcome to another episode of Two Bears, One Cave. I've never seen somebody that is the opposite of the usual person that sits in this chair. We're going from grotesque, visually impaired looking human. Somebody that is offensive to the eyes, to the. An absolute pleasure, a gentleman, a legend. Give it up for the undertaker, everybody. Let him hear it. And don't forget that WrestleMania takes place Saturday, April 18th and Sunday, April 19th, 2026 in Allegiant Stadium in Las Vegas. Vegas. And tickets are available now.

B (0:58)

Bam.

A (0:59)

Damn.

B (1:00)

Damn. You're pretty good at this, bro.

A (1:01)

I mean, you know, done a few thousand of them.

B (1:03)

A few thousand of them.

A (1:04)

Yeah, that's. That's pretty cool that Allegiant Stadium is gonna. It's so wild. Having watched the evolution of WrestleMania and I was watching that one of the docs about like the first time that I think Vince was like, I think we can do a stadium. And people were like, a stadium? Are you crazy? And then, and then I think it was in New York, right? It was a giant stadium.

B (1:26)

So the, the, the first stadium show, I believe was the old. The, the one in Detroit. Not the, not the one with the SkyDome.

A (1:37)

Sky.

B (1:38)

That's Toronto, isn't it? Skydome.

A (1:40)

Yeah, I think you're right. But it's. Is it where the Lions used to play?

B (1:43)

Yeah, yeah, yeah, yeah. They've got a new stadium now. But this is, this is kind of wrestling history. I should know this. Yeah, yeah, it was what, 80, 90,000? It was ridiculous. Yeah. And they filled that thing up and.

A (1:56)

And that must have been like eye opening to everybody. Like, oh, this is. Yeah, we can actually do this.

Summary

2 Bears, 1 Cave: Tom Goes One-On-One With The Undertaker!

Podcast: 2 Bears, 1 Cave with Tom Segura & Bert Kreischer
Host: Tom Segura
Guest: Mark “The Undertaker” Calaway
Producer: YMH Studios
Date: October 27, 2025

Episode Overview

In this special episode, Tom Segura sits down solo with wrestling legend Mark Calaway—better known as The Undertaker. The conversation dives deep into Mark’s transition from college athlete to wrestling icon, the evolution and legacy of The Undertaker character, backstage stories, the physical toll of wrestling, parallels between stand-up and wrestling, and memorable anecdotes involving fellow athletes and celebrities. Throughout, the tone stays witty, candid, and reverent, as Tom and Mark swap stories and jokes.

Key Discussion Points & Insights

The Evolution of WrestleMania and Wrestling’s Popularity

Stadium Shows & Wrestling's Growth:
- Tom marvels at how WWE went from small venues to massive stadium shows, referencing the early risk-taking of filling arenas and the spectacle it became.
  - “Having watched the evolution of WrestleMania...I think Vince was like, ‘I think we can do a stadium.’ And people were like, ‘A stadium? Are you crazy?’” (01:04, Tom)
- Undertaker recollects the historic shows, confirming the significance of Detroit’s venue with 80-90,000 fans. (01:37)

The Grind: Life on the Road

Shared Challenge with Stand-Up:
- Tom and Mark compare the relentless travel and performance grind of wrestlers and comedians.
  - “We were talking about like doing doubles...how you hit an age basically where you're like, I don't want to do two of these, man...that lifestyle feels very parallel.” (04:40, Tom)
- Undertaker notes the “addiction” of being on the road and how returning home is an adjustment. (05:18)
  - "You're home for a couple of weeks, and then you're just like, yeah, I need to go again." (04:58, Undertaker)

From Basketball to Wrestling: The Accidental Origin Story

Finding Wrestling by Chance:
- Mark shares he played college basketball and got pro offers from Europe, but a persistent friend invited him to a wrestling camp—sparking the idea that lead to his career.
  - “I was in college. I was playing basketball...I'm going to this gym every day. And there was another guy...he was like, ‘Hey man...I want to be a professional wrestler. He said, you should do that with me.’” (07:07, Undertaker)
- He admits he was skeptical, but soon saw the potential for athletic big men in wrestling (late 80s). (08:44)

The Moment of Transition

Defining ‘I’m a Wrestler’ Moment:
- After a physical incident in basketball practice, Mark realized wrestling was his true calling.
  - “I jump up really quick and I step on him. I step on his chest. And I was like, listen, you ever cut me like that again, I'll break your f**ing neck...at that moment I was like, I'm a wrestler, dude. I'm done.”* (15:38, Undertaker)

Developing The Undertaker Persona

Performance & Reinvention:
- Mark’s true challenge in his early career was not athleticism but personality and marketability. He credits the creation of The Undertaker character to Vince McMahon’s vision, modeled after an old western mortician.
  - “He came up with the whole character, which was based on the Undertaker...he kind of handed it over to me and said, ‘Okay, now make it yours.’” (24:11, Undertaker)
- Drawing inspiration from horror movies and adding personal touches led to the character’s massive success.
  - “I’m watching all of Friday the 13th movies...trying to take little bits of all of them and incorporate them and make them my own.” (25:06, Undertaker)
Initial Doubt & Overnight Impact:
- Mark acknowledges the potential for the gimmick to turn corny, but its uniqueness resonated.
  - “You’re right, you don’t want something to be...that really has the potential to be really corny. I think it was so different at the time that it resonated.” (25:06, Undertaker)
- Within four years, he found himself wrestling Hulk Hogan, with unexpected crowd support.
  - “By the time that I wrestled Hogan in ‘91…crowd was...60/40 in favor of me.” (26:22, Undertaker)

Legacy, Longevity, and Reinvention

Staying Power:
- Mark attributes his decades-long relevance to constantly tweaking the Undertaker, both visually (changing colors, gloves) and in-ring moves.
  - “You can never be content in this business because there's so much content being produced.” (30:11, Undertaker)
  - “Just changing it to purple...just like, oh, that's different.” (31:07, Undertaker)

The Physical Toll

Injuries & Surgeries:
- Mark lists an extensive catalog: knees, hips, eye sockets, being set on fire, muscle tears, concussions—culminating in 18 surgeries.
  - “I've had both knees replaced at this point, partial hip replacements...I've blown out both eye sockets...I've been set on fire twice...” (32:49, Undertaker)
Mentality of the Old School:
- The old attitude was “if you can get to the ring, you go to the ring,” with minimal medical support. He recognizes the drastic improvements in athlete care today.
  - “Now we have doctors ringside, trainers...athletes are very well taken care of now. Not so much...in the 1980s.” (33:24, Undertaker)

Protecting the Mystique

Dedication to Kayfabe:
- Mark maintained character off-camera, rarely breaking Undertaker’s mystique, rarely doing media, and even always dressing in black in public.
  - “If you saw me in the airport, there'd be no doubt who that was. I was always dressed in black...I lived it.” (39:51, Undertaker)
  - Tom compares this to “method acting” and great actors’ devotion to their characters. (40:21, Tom)

Wrestling’s Athletic ‘Freaks’

Who Impressed the Undertaker:
- Mark Henry, Kane, Big Show, and especially Brock Lesnar get praised for freakish strength and athleticism.
  - “Brock’s what, 6’3”, 295 in his first run...there's no way he can be as fast as he is...he was a freak of an athlete.” (43:52, Undertaker)
- Newer generations (e.g. Bron Breaker running 22-23 mph at 240 lbs) push boundaries further. (45:26)

Favorite Matches & The Art of Storytelling

WrestleMania 25 vs. Shawn Michaels:
- Mark singles out this match as his most perfect, blending athleticism with compelling storytelling.
  - “As far as a wrestling purist kind of matches would have to be WrestleMania 25. Shawn Michaels. That was as close to perfect that I ever got.” (48:18, Undertaker)
- Reiterates wrestling is “a soap opera with violence.” (50:10, Tom)

Behind the Curtain: Locker Room Culture & Training

Chattel in the Ring:
- Some wrestlers are stiffer than others; Mark tolerated roughhousing as long as he could return the favor.
  - “Don't hit me hard in the nose or face...but if you want to work snug, I can work snug. Just don't bitch when it comes back.” (58:16, Undertaker)
- Today’s environment is more professional with vastly improved recruitment and training. (59:04)

Life Outside Wrestling

Buying Stupid Stuff:
- Mark shares buying a new Harley as his first “I’ve made it” purchase. Now he prefers pickups over motorcycles due to safety and mobility issues.
Parking Lot Mishap:
- Incidentally ran over a low car at Whole Foods—luckily, the owner was a fan happy to meet The Undertaker. (62:37)

Crossing Paths with Legends

Meeting Mike Tyson:
- Both recall being starstruck by Tyson, despite their own fame. Mark describes Tyson as a “kid around wrestling” and an encyclopedic fan.
  - “He’s like a little kid when he's around wrestling...he lights up. The stuff he knows blew me away.” (65:01, Undertaker)

Lessons on Humility

Tom’s Praise:
- Tom lauds Undertaker as down-to-earth and authentic, despite his intimidating legacy:
  - “You're such a genuine, authentic, nice man...It’s a real pleasure to be around, so.” (67:52, Tom)
- Mark, in classic fashion, responds self-deprecatingly:
  - “As seriously as I take what I did and what I do, I don’t take myself as serious… I feel like I've been incredibly blessed.” (67:55, Undertaker)

Notable Quotes & Moments (with Timestamps)

“If they're indifferent towards you, you're not going to have a long career.”
- —Undertaker, on the necessity of audience investment (18:52)
“For years I didn’t interact at all with...the fans...now, I'll do signings...my One Dead man show, which is a really cool experience for a wrestling fan.” (37:35)
“I always wanted people...when they saw me, even in public, I wanted [them to] go, ‘Yeah, no, I ain't with that guy.’” (39:09)
“Wrestling is a soap opera with violence.”
- —Tom, on wrestling’s unique appeal (50:10)
“Brock Lesnar...there's just, like, there's no way he can be as fast as he is. Your eyes and your brain can't comprehend someone this big moving like this.” (43:52)
“You want to pay to see them kick someone’s ass or get their ass kicked. Either way, as long as they care.”
- —Undertaker, on wrestling personas (19:03)
“As seriously as I take what I did and what I do, I don't take myself as serious. So, I mean, it's...I'm in a great place.” (67:55)

Timestamps for Important Segments

WrestleMania's Stadium Era & Early Days: 01:03 – 03:04
Comedy & Wrestling: Shared Road Grind: 04:40 – 06:33
Origin Story (Basketball to Wrestling): 06:36 – 11:37
Transition Story: “I’m a Wrestler” Moment: 15:38
How The Undertaker Character Was Born: 21:17 – 25:46
Staying Relevant & Reinventing: 29:45 – 31:22
Long-Term Physical Toll, Surgeries: 32:32 – 36:21
Protecting the Character in Real Life: 39:09 – 42:50
Strongest Wrestlers & New Era Athletes: 43:52 – 45:26
Best Match: WrestleMania 25 vs. Shawn Michaels: 48:18 – 51:01
Backstage/Locker Room Culture: 51:56 – 59:04
Materialism, Motorcycles, & Trucks: 60:25 – 62:38
Mike Tyson Encounters: 64:02 – 66:55
Reflections on Humility & Legacy: 67:52 – End

Final Thoughts

This episode is a must-listen for wrestling fans, sports aficionados, and anyone interested in the mechanics of iconic performance. Mark Calaway peels back the curtain on the persona of The Undertaker, revealing the grind, strategy, and devotion behind his legacy. Tom Segura’s mix of irreverence and genuine admiration ensures an entertaining, revealing, and surprisingly relatable conversation—covering everything from in-ring psychology to parking lot mishaps.

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Tom Goes One-On-One With The Undertaker! | 2 Bears, 1 Cave