Tom Goes One-On-One With The Undertaker!
2 Bears, 1 Cave with Tom Segura & Bert Kreischer
October 27, 2025
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.
Speakers Tom Segura, Mark Calloway
TopicsComedySociety & Culture
Tom Segura (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 tomsegura.com/tour.
All right, welcome to another episode of 2 Bears 1 Cave. I've never seen somebody that is the opposite of the usual person that sits in this chair. We're going from a grotesque, visually impaired looking human, somebody that is offensive to the eyes, to an absolute pleasure. A gentleman, a legend. Give it up for The Undertaker, everybody. Let them hear it. And don't forget that WrestleMania takes place Saturday, April 18th and Sunday, April 19th, 2026 in Allegiant Stadium in Las Vegas. This and tickets are available now.
Mark Calloway (0:58)
Damn.
Tom Segura (0:59)
Damn.
Mark Calloway (1:00)
Damn, you're pretty good at this, bro.
Tom Segura (1:01)
I mean, you know, done a few thousand of them.
SPEAKER_4 (1:03)
A few thousand of them?
Tom Segura (1:04)
Yeah.
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? What are you crazy? And then I think it was in New York, right? It was a giant stadium.
Mark Calloway (1:26)
So the first stadium show, I believe, was the old... The one in Detroit, not the one with the... Sky Dome? No, no, no, that's Toronto, isn't it? Sky Dome?
Tom Segura (1:40)
Yeah, I think you're right. But is it where the Lions used to play then?
Mark Calloway (1:43)
Yeah, they've got a new stadium now. But this is kind of wrestling history. I should know this. But yeah, it was, what, 80, 90,000. It was ridiculous. Yeah. And they filled that thing up.
Tom Segura (1:56)
And that must have been like eye-opening to everybody, like, oh shit, this is, we can actually do this?
Mark Calloway (2:01)
Yeah. And they did that one. And then we still went back and did a few arena shows. My first mania was at the old sports arena in LA.
So-
Tom Segura (2:15)
Down, like what, like down the Forum? Like down there?
Mark Calloway (2:17)
Yeah, not the Forum.
Tom Segura (2:18)
It was called the Sports.
Mark Calloway (2:19)
The Sports Arena. I think that's where the Clippers originally played.
Tom Segura (2:22)
Okay.
Mark Calloway (2:23)
And, you know, yeah, we weren't even, yeah, we couldn't even handle the Forum at that point.
Tom Segura (2:31)
Well, you're part of the group of people that helped obviously transcend, like, the lines of popularity and the reach of this sport. I mean, you started when it was still-
Mark Calloway (2:46)
Yeah. I mean, it was, we had already had a really, really good run. Like, that Hulk Hogan run at the end, at the late 80s, was just, that's what took it, I think, to-
Tom Segura (2:58)
New heights, for sure.
Mark Calloway (2:59)
Yeah, to new heights where it just wasn't that old carnival atmosphere.
Tom Segura (3:04)
But your early days were some of, like, smaller venues. Yeah, because one of the things, like, when we met, for people, I've said this before, but for people they don't know the way we met, it always makes me laugh. Because I was having a home gym put together, and I was ordering equipment, and I was talking to this guy who was doing it for me, and I said, oh, I want a piece of equipment that another company makes. And he was like, that's fine. But he goes, you know, we make something similar.
Mark Calloway (3:36)
Right.
Tom Segura (3:36)
I said, well, you know, I'd like to say yes, but in order for me to feel comfortable, I'd really like to try it before that.
Mark Calloway (3:43)
Which is smart, with gym equipment.
Tom Segura (3:44)
With gym equipment.
Mark Calloway (3:45)
Yeah.
Tom Segura (3:45)
And he goes, well, I have a client in the area, and he would let you try it. And I go, okay. And then he just sends me a group text. Hey, Mark, this is Tom. He'd like to try it. And you're like, sure. And then he sends me a text separate. He goes, Mark is the Undertaker. I go, you want to fucking lead with that, dude? Then I'm texting the Undertaker? He was like, sorry. So I think that was Dustin, maybe?
Mark Calloway (4:09)
Yeah, Dustin Riddle, I believe.
Tom Segura (4:11)
Great guy. And by the way, they do great work, Soarenex people. So I went over to your house, well, your under construction house. But your gym was done.
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