The Undertaker Reveals His Greatest Match, Kayfabe Secrets, Career Surgeries

The Undertaker Reveals His Greatest Match, Kayfabe Secrets, Career Surgeries – During a candid interview with Tom Segura on 2 Bears, 1 Cave, WWE legend The Undertaker opened up about his storied career, revealing which match he considers the best of his life, the extreme lengths he went to maintain his iconic persona, and the toll wrestling has taken on his body.

When asked about his greatest performance, The Undertaker immediately pointed to his unforgettable showdown with Shawn Michaels at WrestleMania 25.

“So the match I’m probably… man, as far as a wrestling purist kind of match, would have to be WrestleMania 25. Shawn Michaels.”
“That was as close to perfect that I ever got.”

He explained that both he and Michaels were in their 40s at the time, well into the back half of their careers, which only made their performance more powerful.

“We were both in our 40s, both late in our careers. But the story we were able to tell? That’s what wrestling is all about. Wrestling is a soap opera with violence.”

The match wasn’t just physically intense—it played with the emotions of the audience. Fans were fully invested, unsure if The Undertaker’s legendary undefeated WrestleMania streak would finally be broken.

“They all thought there was a chance I was going to lose the streak. That’s the goal—you want them to go through that emotional ride.”

The Undertaker also discussed how seriously he took protecting the mystique of his character, avoiding public appearances and media to maintain his aura.

“It paid off, I guess, but once I started being The Undertaker, everything was focused around that character. I always wanted people — even if they knew I wasn’t really dead — to look at me and think, ‘Yeah, I’m not messing with that guy.’ There’s something different about him. So, I didn’t do a lot of media or interactions. I lived that character.”

His commitment wasn’t just backstage either. The Undertaker said he kept the act going at airports, fan encounters, and everyday life—always dressed in black, never out of character.

“People always ask how I lived it, and yeah, I really did. Like now, I’ve got yellow tennis shoes on and jeans, but back then, if you saw me at the airport without my wrestling gear, there’d still be no doubt who I was. I was always dressed in black. I kept it going, and I lived it. That’s the way I approached it because the character is so unique and so different. I didn’t want people to see me on TV and think, ‘Whoa, that’s death,’ and then run into me in public wearing a Hawaiian shirt and a fedora and go, ‘Huh? That’s bulls*’”

Now that he’s stepped away from the ring, Taker says he’s enjoying life with a bit more personality—and even pokes fun at himself for showing up so often despite being retired.

“Yeah, I’m able now to obviously have a little more personality and not be so deadpan with the character, so that’s fun. You know, I think sometimes I get a little overexposed for not being able to actually go and have a match. It just becomes difficult. You’ll get your naysayers like, ‘Oh, well, you got the old man out there doing stuff.’ You know, it’s like, well, there must be a reason they keep asking, right?”

One of his favorite post-retirement outlets has been the One Deadman Show, where fans hear his personal stories in an exclusive setting with no cameras allowed.

“But yeah, I like my role. For years, I didn’t interact at all with the fans, and now I’ll do signings every once in a while. I don’t do a lot of them, but I do enough to get out there. I also do my One Deadman Show, which is a really cool experience for a wrestling fan and an Undertaker fan, because you actually get to hear a lot of the stories — even things that I don’t say on my podcast or someone else’s podcast. In the One Deadman Show, we take the phones and don’t allow recording, so you really get an uncensored experience. That’s pretty rad for a fan.”

The Deadman then turned to the physical price of his career, listing a staggering 18 surgeries.

“Well, let—how long we got? I can run them down,” he began before listing years of damage. “I’ve had both knees replaced at this point, partial hip replacements. That’s just from the wear and tear. But like acute injuries? I’ve blown out both eye sockets—I’ve had orbital blowout fractures in both eyes. I’ve been set on fire. Actually, I’ve been set on fire twice.”

Then came the insane number that would even shock longtime fans.

“Torn muscles, concussions, numerous lacerations, broken bones… 18 surgeries total to replace and fix wrestling-related injuries.”

The Undertaker explained that his generation of wrestlers didn’t have the medical safety protocols that today’s stars do. Back then, it was all about getting to the ring no matter how bad you were hurt.

“Back then, if you could figure out how to get to the ring, you went to the ring. And if you got hurt during the match, you did your best to get out of it.”

He also praised the modern WWE system, noting how far athlete care has come since his days on the road.

“Now we’ve got doctors ringside, trainers—it’s treated like a major league sporting event. The athletes are very well taken care of now. Not so much in the ’90s and before.”

Even after enduring nearly two dozen operations and countless injuries, The Undertaker said he has no regrets about the grind that made him a legend.

“I try not to complain about it because I knew the whole time that eventually something was gonna break. You don’t play the game that hard and not have residual effects.”