The inside stories that define The Undertaker’s enduring WrestleMania legacy

Mark Calaway has walked into WrestleMania 27 times as The Undertaker. He has won 25 of those matches, including 21 in a row, before Brock Lesnar broke “The Streak” in 2014 and Roman Reigns added a second loss in 2017.

The Undertaker’s streak became the stuff of legend — the centerpiece of a career that has carried on over four decades. The Streak crystallized why Calaway has long represented the beating heart of the WWE locker room, and it made facing The Undertaker at WrestleMania a badge of honor.

“It was a bucket list situation to say I shared the ring with him,” Reigns said. “You’re dealing with The Undertaker; you’re dealing with so much more than one match. It’s the legacy and the influence. The trademark of him, like how his name echoes through the hallways backstage. We have traditions named in his honor. Like the ‘Taker Shot.’ We all gather up after every tour at the hotel or in catering. We give a toast to whoever led the tour, like the veteran in the main event. It’s always been known that after the main of the last show, you get everybody together and get these shots together, because we have to do the ‘Taker Shot.'”

Through “The Last Ride” documentary series, the world has learned what it was like for The Undertaker to maintain his aura of mystery and secrecy for 30-plus years while living up to the pressure of performing at WrestleMania.

The legacy that began with a win over Jimmy “Superfly” Snuka in 1991 and continued through this year’s cinematic “Boneyard” match against AJ Styles is undeniable. But what was it like to compete against The Undertaker?

ESPN spoke with 10 opponents of the Undertaker — and one referee — about what it was like to hear the “gong” of his entrance theme song, to take a Tombstone piledriver in front of 80,000 fans and to help write another chapter in a wrestling legend: Jake “The Snake” Roberts (WrestleMania VIII, 1992); Kane (Glenn Jacobs) (WrestleMania 14, 1998, and WrestleMania 20, 2004); Ric Flair (WrestleMania 18, 2002); Matt Bloom, aka A-Train (WrestleMania 19, 2003, with The Big Show in a handicap match); Randy Orton (WrestleMania 21, 2005); Edge (WrestleMania 24, 2008); referee Jimmy Korderas (WrestleMania 24); Shawn Michaels (WrestleMania 25 and 26, 2009 and 2010), Triple H (WrestleMania 27 and 28, 2011 and 2012), Shane McMahon (WrestleMania 32, 2016) and Reigns (WrestleMania 33, 2017).

What was it like when you found out you were facing The Undertaker at WrestleMania?

Ric Flair: I was shocked. I was horrified. I felt like I was being put in a position that would come around once in a lifetime. And I can’t tell you the pressure I put on myself, because I didn’t think I was ready for it. I certainly appreciated the fact that he picked me, which I couldn’t believe, because he could’ve picked anybody.

Kane: It all started when I found out I was going to be Kane. I was really excited because I’d have the opportunity to work with the Undertaker. Initially, it was presented as a one-off, and then of course it evolved into a storyline that would culminate at WrestleMania 14. I was excited. I was also intimidated, because it’s the Undertaker. It’s like saying, “Hey, you’re the third-string backup, here’s the Super Bowl, go knock ’em dead, kid.” It’s kinda the same thing.

Triple H: That [first WrestleMania] match was put together at the very tail end leading into WrestleMania. We both found ourselves in a position where we didn’t have [anything booked]. I don’t remember whatever he was doing, and to be honest, I don’t remember what I was doing — both things evaporated at the same time, and we found ourselves in a position where they were saying, “What about Taker? What about Triple H?” We were both like, “Yeah, I’ll do that.”

Randy Orton: They had me slap him, if I remember correctly. And that was going to get his attention. I was the “Legend Killer.” I had a good 2004. It was like, “Tonight you’re going to start your angle with Taker going into WrestleMania. Just haul off and slap him. And make sure you slap him real good.” And I’m thinking, “Holy crap, the receipt on this is gonna be something for the ages.”

Edge: Initially, I was in the Money in the Bank match [at WrestleMania 23], and I was supposed to win that match. And that would have kept my undefeated streak at WrestleMania intact. It was changed the week of, with Mr. Kennedy winning it. I voiced my concern, saying, “OK, I understand you want to go a different direction … however, if we are still going this way with Taker next year, to me there’s a lot more intrigue if you have two people undefeated [at WrestleMania].” [Later], my idea was that [The Undertaker] had never defeated me in any of our matches. So it was, “Maybe this guy just has Taker’s number?”

Jake Roberts: It was a troubling time for me. I’d had an argument with Vince McMahon, and it did not go well. And I basically told him I would wrestle that one last match for WWE at the time. Being in the ring with Mark was always a pleasure. I schooled him quite a bit in the early days. I remember him coming to me and saying, “I want to ride with you.” Like, I don’t think you need [that]; you’re not ready for my “act.” I’ll drink you under the table; I’ll make you sick. So, the challenge was out, and off we went. And after a couple months, he was pretty damn near dead. Trying to follow my act, you know, which I’m not proud of now. I’m clean and sober.

Roman Reigns: I remember the conversation with Vince. I saw Taker like a week prior, and he almost gave it away, but he did good in covering it up. He could tell I didn’t know yet. When Vince explained it to me, I was just in awe. It’s something that everybody who gets into the business wants, to get into the ring with The Undertaker. And I remember the first thing I thought was that I wanted to put him over. I wanted to lose. Immediately, that was my instinct. Out of respect. I knew he was in pain, but I didn’t know he was going in [for hip surgery] soon after that or else I would have crafted that story a little differently. So I knew it was on me to try to help carry it. The movement of the match. Orbit around him. But I thought it would have been a better story if I was on my back at the end. Obviously, it didn’t go that way.

What was memorable about the lead-up to the match?

Orton: I inducted my father [Bob Orton Jr.] into the WWE Hall of Fame that year, and I practically got booed off the stage. The people were very into this match.

Matt Bloom: We actually went up to Taker’s ranch, and we spent some time talking about [the match]. And, you know, I remember it was going to be a tag match, and a few days before that, Taker called us up and let us know that creatively it changed. We had to make some changes [taking Nathan Jones out of the match], and we just went with it.

Shane McMahon: Prior to the match, Mrs. Calaway, Mark’s mother, comes up to me at a dinner a few days before WrestleMania. I’ve known her for a very long time. I ask her how she is, give her a hug. Then she grabs me with both arms and stands me back. She says, in this Texas drawl, “You know, you’ve always been one of my favorites. However … you hit my son right in his eye and made him bleed [on Raw]. You went down a couple of notches in my book.” She was scolding me! And I look over at this big, huge Mark Calaway bowing his head very humbly, thinking how embarrassing this moment is. But it doesn’t matter how badass you are. There’s going to be a protective mother.

Shawn Michaels: The biggest concern [was topping as big a match as we had at WrestleMania 25]. It was very much an issue, very much talked about. I feel like we both felt that the “Streak vs. Career” stipulation obviously helped. We had at least gotten to the point in our careers where you worry about that topping factor, but you don’t quite apply the pressure to yourself that you did when you were younger. We had some different dynamics to the story. If all of that is fresh, then technically the only thing that’ll be the same [as the previous match] are the two guys. You have to do your best to rationalize it, as best you can. Because the big pink elephant in the room is, “Can you follow it?”

Triple H: Obviously coming off of the two back-to-back matches that Shawn and Taker had, which were two of the greatest matches ever, there was pressure to deliver something really special — on both of us — and I feel like we did in both of our matches.

Edge: I was in a dressing room with Dave [Bautista]. It was a tent. I remember how hot it was. I remember smelling barbecue. I walked out, and I realized it’s because Snoop Dogg’s bus was parked next to our tent. They were having a big ol’ barbecue. They were having fun, but I needed to get into business mode. I didn’t watch any of the other matches on the card, because I didn’t want them in any way to get in my head or in any way affect what I was going to do.

What was it like to experience The Undertaker’s entrance at WrestleMania?

Triple H: You stood there waiting for him to get to the ring just in awe. Not only on the entrance, but the whole time that you were in there … it was epic.

Bloom: I had the opportunity to work sold-out, or almost sold-out, Tokyo Dome shows and really big other live pay-per-views. [WrestleMania against The Undertaker] was special. Everything about it. I remember being a Limp Bizkit fan and thinking, holy s—, like this is pretty cool [as Limp Bizkit played The Undertaker to the ring in a live performance by the band].

Reigns: Every single step that he takes to the ring, he’s thought about it. Every movement. Every inch of his entrance.

McMahon: There’s something so very special and ominous during his [ring] entrance. The house goes dark. The crowd goes bonkers. Goose bumps explode all over my body. I remember thinking, “OK, I’m about to go to war. I’m about to have my ass handed to me. I gotta be sharp.” There was a big strong boy coming to get me, and he was pumped. He had like 20 cups of coffee in the back.

Were you nervous ahead of your match with The Undertaker at WrestleMania?

Orton: Some of these guys say they don’t get nervous. We all get nervous, more or less. And I’ve always been a guy where if they’re counting down the hours before a match, I’m always in my head. It was no different back then. I knew I had something special. I don’t think I fully appreciated that opportunity then as much as I could have.

Roberts: A lot of guys, they get all crazy inside, whenever you say WrestleMania. To me, it was another day at the office. You know, I didn’t go out and do anything different. I didn’t go out and go way over the top. I went out and did what got me to the dance, you know? And that’s where a lot of guys miss; they do something completely out of character. And therefore they’re cheating the fans, because the fans pay to see their main character. So that’s my feeling, man. I mean, I used to watch guys drive themselves insane, getting ready for a WrestleMania match. Are you freaking kidding me, man? Go out and do what got you to that day. I know, you don’t need to change anything.

Kane: I got thrust into the situation that, in my heart, I knew I could do but hadn’t proved it to anyone yet. Including myself. So the first person I had to prove it to was myself. I was excited. I was a little scared, frankly. Then when we get to WrestleMania 14; at that point I had my sea legs under me. I knew I belonged there. I know I could do this.

Flair: I was horrified that I would let him down and the company. You’re in an event of that magnitude. WrestleMania is just as big as the Super Bowl, NBA championship, World Series; to me, it’s on par with anything big in sports. It just is: 80,000 people; it’s insane. And I thought, God, here I am, 55 years old, going to fight him at 56, and I’ve got to pull off my end. And I was mortified.

McMahon: I just remember my adrenaline was pumping so high at the start that I jumped high and kicked him right in the chest, really hard, to set the tone. Because he’s my friend, and you take more liberties with your friend than you would anyone else. So I waffled him. All of a sudden, I get this barrage of hands — pow, pow, pow — and I’m like, “Oh, my God.” Three shots. I was on my heels. I was like, “Oh, he’s mad.”

Jimmy Korderas, referee: I found out about two weeks prior to WM that Edge and Undertaker requested me to be the official for their match. While discussing the match the day before with Undertaker, Edge and producer Michael P.S. Hayes, it was decided that I would be “taken out of the match” via a referee bump. I was asked if I would be OK with taking a big boot from the Undertaker. Without hesitation I said yes! Inside, I’m thinking a big boot from the Undertaker, how would I not be OK with that! After all, it is The Undertaker. Of course, I’m cool with it. We came up with the right sequence of moves that would lead to the kick that would take me out. Taker sensed I was nervous and did his best to calm my nerves. The night before, I had trouble sleeping. I was wired and just couldn’t relax because I was worried about making the big boot look good.

At 2 a.m. I went for a walk outside the hotel. While sitting on a bench outside, I was approached by WWE superstar Ken Kennedy. He asked why I was up so late, and I told him my concerns about the match, and especially my concern about taking the boot. He told me not to worry, I was in that match for a reason and it will be evident when it’s all over with. I thanked him, went back to my room and got a little sleep. [After the match], I went to Undertaker to thank him not only for the match, but for having faith in me and allowing me to be a part of this special moment. He took my hand, thanked me and said it was a pleasure working with me. I had tears of joy and happiness that I could not hide. Taker put his arm around me and said he was proud of me. For me, there is no better feeling than that.

What is your most vivid memory from your WrestleMania match against The Undertaker?

Flair: He’s 20 years younger than me, and when I missed the flip in the corner, he backed me up and said, “Can you make it this time, kid?” Keep in mind that he’s calling me kid and I’m 20 years older. I went over the top, he booted me, and the rest was history.

Michaels: I did what I basically do with people that I trust and know “have it,” so to speak. You’ve got your main points, but everything else you sort of feel — and see where it goes. That’s how that [match] worked. You’ve got your signposts in the road, you have an idea how to get there, but then you just see how it goes. And we knew we were going to be there for a while.

Roberts: [Vince] said he wanted me to go out and do certain things in the match that I didn’t agree with, such as dropping The Undertaker twice with the DDT, a maneuver that I invented and nobody else had ever gotten up from. He wanted me to do it twice [and then lose]. Well, I did it twice. I just didn’t cover him [for the pin]. [Laughs] You know, which kind of says, “Screw you, Vince.” That wasn’t the right thing to do at the time. Hindsight is 20/20, and it didn’t matter; I still need to go out and do my job to the best of my ability, which I did not do.

Orton: I’ve seen clips of the RKO out of the chokeslam. I remember thinking that would be a tough reversal to pull off, because I’m not the most agile guy. But we pulled it off. I remember for the finish, I picked him up in the Tombstone [piledriver], and then he reversed it. That Tombstone, man … he’s the only guy that’s allowed to do a piledriver. Even being upside down, being prepared to be spiked on your head, I don’t care who’s got you. It’s a little scary. Even for guys that can do it in their sleep.

Edge: Our match was basically the last time that you saw Taker going for the title at WrestleMania. And, sure, a character like [Taker] doesn’t necessarily need the title. He’s an attraction to us. What Andre The Giant was, essentially. But every once in a while, it’s good to see them in those title matches.

McMahon: [Mark] was not a proponent of me jumping off the cage. Not taking anything away from [Mick] Foley, but this was the new Hell In A Cell. This was bigger, substantially higher. Mark would say there were other things we could do, different iterations. But I told him no. This is what the story needs. It was David vs. Goliath, and you’re expecting David is just going to be killed. In that match, I had exhausted everything in my toolbox to try and win. This is what WrestleMania needs. I blew my bellybutton out — an umbilical hernia — because I hit so hard [on impact]. I didn’t expect that force to be that hard. But oh, my God, it was.

How do you feel about not breaking The Undertaker’s WrestleMania winning streak, which Brock Lesnar eventually did at WrestleMania 30?

Bloom: I feel like I knew about The Streak a little bit before our match, and what made the match so cool is I thought that we could do a good job creatively of making everyone believe that The Streak could be in jeopardy. He has two people he has to fight. And not just two ordinary people. They have the Big Show and A-Train, and I think everyone in that match was — I don’t want to speak for Taker or Big Show — but I feel like we were all in our prime, bodywise, we felt good. We’re moving well, so I just thought, “Wow, we’re gonna be able to really tear that stuff in there.”

Edge: [Calaway’s wife] Michelle McCool has done interviews where she kind of let everybody know, at one point, I was asked about ending The Streak. To me I didn’t think The Streak should end. So I said no. What am I going to gain from [ending The Streak]? Sure, there’s this, that and the other, but I already had heat. I was already established. To me. It didn’t need to be ended. And I still don’t think it should have been ended until what would be, or will be, his last match.

Michaels: I’ve been on record as being one of the guys uptight about seeing The Streak being broken. We all felt like that was something that was always just going to be there. Once The Streak got so established, everyone from a creative standpoint asked when we should do it. But it would be brief, and then they’d say, “Gosh, no.” For me, I was ready [to keep The Streak alive]. All these years later, I’m comfortable with being one of the guys that was ready for that big decision. That made it a ton easier for everyone involved.

What was the aftermath of your WrestleMania match against The Undertaker?

Flair: He put me back on the map. It’s as simple as that. In the end, he took care of me, and the rest of it is history.

Triple H: Knowing that through the Attitude Era, through everything, we were three guys that had earned each other’s respect, three guys that were really close friends and had been through everything together and watched as people around us — the Austins and the Rocks and the Foleys — move on, and we’re still here and we’re still plugging away. When the end-of-an-era thing was brought up, for us it was kind of [for real]. It was the end of our run. Probably the last time that all of us would be in a ring, especially at a WrestleMania like that, all together. It was a moment. And at the end of that last match, with Shawn as a referee, with the three of us standing on top of that stage, we turned around and looked back over that crowd, it was absolutely real and emotional. One of my favorite moments ever in the business, and I’ll never forget it.

Kane: It was one of the most special matches I’ve ever had because it was the culmination of what I think is the greatest storyline in WWE history. Looking back, I would’ve been happy, really, if that was the high point of everything. But it wasn’t. It was just kicking off. Instead of it being the end of Undertaker vs Kane or Undertaker and Kane, it almost ended up the real ignition for many years, either against one another or as the Brothers of Destruction teaming up with one another.

Reigns: When I went through gorilla [position] and he was still in the ring, I was just tucked off from the ramp into this little tiny holding area where people do last-minute [preparations] before a match. I just sat in one of these little chairs and I cried. It was such an emotional overload, for bad reasons and for good reasons too. As a perfectionist, I think Mark can agree that we had such an awesome story. If it had all went perfectly … aw man, it would have been so fire. But the opportunity to main event a WrestleMania with Taker, I was so grateful. But the perfectionist in me could not let it go. It ate me up. It still bothers me a little bit. I remember my cousins [The Usos] and I skipped out on the after-party, and I didn’t get back to the hotel until like 2 a.m. because we drank all night and talked. I probably shed a few more tears that night too. I had so many hopes and aspirations to take advantage of that man’s time and do right by him, and I just felt like I failed that situation. And it just lit a fire under my ass. I don’t think I had a bad match since.

What does The Undertaker mean to you as a wrestler?

Roberts: I knew that he was going to be there a long time, because he was smart. You know, he was business smart. I wasn’t business smart. He knew how to play the game. He knew when to say no and when not to say no. So yeah, I definitely saw him going a long way. He took care of himself.

McMahon: The Undertaker is singular and iconic. The character is just awesome, and it’s grown. It’s been the connective tissue [of the WWE], not only from an audience standpoint, but also linking in multiple eras of superstars. It’s kind of like if Michael Jordan was still playing and performing at a high level. What Jordan is to basketball is what Undertaker still is to the WWE.

Orton: That was my second WrestleMania. I was still green. I didn’t know then how to appreciate that for what it was. Undertaker is Undertaker. The respect factor was there. But looking back now, 15 years later and seeing everything he’s done … man, he was The Undertaker then, but man is he The Undertaker now. Watching that “Last Ride” documentary, for the first time in 30 years letting us in? Showing us that he’s a human being? I mean, I remember years ago you never thought about him breaking kayfabe or talking about his hip surgery or how he wished he could have had a longer time for a match against John Cena at WrestleMania. That’s just forbidden! But times have changed, the business has changed, kayfabe is dead. I was 50-50 for a long time on it, but I can see where it helps our fans understand us more as human beings, which I think is important.

It’s easy to forget that we don’t hurt physically, mentally and emotionally. Then there’s the whole, “Aw, wrestling’s fake,” which always really pissed me off. If you get a fan that says stuff like that to watch “The Last Ride,” then you’re going to see a man who’s given his body to the business. Professional wrestlers are one of a kind when it comes to that. You can’t really compare us to anybody else.

Edge: There will never be another Undertaker. There will never be an enduring character like that. If you just heard that character on paper you’d go, “Well that would never work.” Well guess what? He took it and made that thing work, with some great booking and great opponents throughout the years, but also some pretty rough opponents too. He still managed to plug his way through all of that and make this enduring character. By reinvention, by retooling a style, by not staying stagnant and comfortable in something that worked, and always reaching to try and find the next thing to do in terms of a metamorphosis. So that’s a huge, huge thing to main event WrestleMania with a character like that, let alone the performer behind the character.

Additional Interviews conducted by Andrew Feldman and Tim Fiorvanti.