Shane McMahon on friendship with Undertaker: WrestleMania 32, hotel brawls and a motherly lecture

The Undertaker and Shane McMahon have been friends since the early 1990s, and while they've interacted several times in the WWE, their most famous clash was inside Hell in a Cell at WrestleMania 32. WWE

Editor's note: In 2016, Shane McMahon, son of WWE founder, chairman and CEO Vince McMahon and himself a WWE icon, returned to the ring after a long stretch away from the company. In his first match back, Shane took part in a Hell in a Cell match against his friend Mark Calaway, aka The Undertaker, at WrestleMania 32 in Arlington, Texas. As "Undertaker: The Last Ride" on WWE Network continues to reveal the man behind the iconic gimmick for the first time, McMahon, in his own words, gets candid about his long relationship with Calaway and the story behind their most memorable match.

As told to Greg Wyshynski. Edited for length and clarity.

Mark Calaway is probably my best friend in the business, and for the longest.

In the summer of 1990, I was back from college and I was staying at my parents' house in Greenwich, Connecticut. My dad would have special talent come out to the house. Mark came walking through my dad's front door. Big, huge, but young -- no tattoos, just an alabaster glow of skin. Oh my god, he was so pale.

I remember he was sitting on the couch that day, looking uncomfortable. He wasn't sitting straight up, just off to the side a little bit. So I asked him if he was OK. He said, "I can't believe it. I only have this one pair of pants. This morning, I got up, leaned down to pick up something and -- POP -- I popped my zipper." I looked right next to his zipper, and there's this giant hole. Now, back in 1990 on a Saturday in New York City, where he's staying, it's not like there's a big-and-tall men's shop that's open super early. So I assured him it was OK, that the chief wouldn't even notice.

We just hit it off. You've got two kids in their 20s, just starting in the business. And that's what our relationship would be built on: trust, respect and looking out for each other.

Mark and I grew up a little differently. He grew up on the independent circuit, where you learn the art of keeping things to yourself, what we call the art of "kayfabe." You look at the way the guys that came before you acted: You don't mess with the family, you don't mess with the money.

That's why you never broke kayfabe. Mark has always had the mentality, as have I, and it's even more enhanced by The Undertaker character. It's mysterious and dark. Mark was very guarded, as he should have been, but now that it's evolved, so has Mark Calaway, the human being. He's grown in life.

On "The Last Ride," you'll see he's struggling, as we all do when we're facing our athletic mortality, where the brain says, "Go!" and the body says, "No." It happens to all of us. Father Time is undefeated, unfortunately.

From a physical standpoint, Mark Calaway is darn near superhuman. He should be a science experiment when it's all done. He's been through the wringer on every single thing and still has the drive to go after it. But I think that's where Mark struggles now. He's not as fast. But you can do different things and tell a different story. Mark has always been about performance. Telling a really great story. He doesn't have to jump over the top rope and fly to the floor. Excuse the pun, but what he wrestles with the most is his own personal feeling of, "Did I give a good performance?"

I've seen that. I'll go back to one specific instance, at Survivor Series in 1991. It was Hulk Hogan vs. Taker for the WWE championship. Mark picked him up and then gave him the Tombstone. It was clear as day, to me, that Mark had protected Hulk, but Hulk claimed that his neck was hurting and that he was stunned for a second. I'll leave it there, whether there was any embellishment from Taker's opponent at that time. Hogan was the icon. Taker was just coming up. It wouldn't have been the first time with those older-school guys vs. the rookie.

I remember Mark walking through the curtain and thinking he had let us down, that he had just messed up the Golden Goose, had screwed it up. He was so upset and distraught. That's how much he wears his heart on his sleeve.

Sometimes working with different individuals, it's all about chemistry. What story you're telling, and the performance coming out of that. If you have two really big guys in there, then that match is going to be different than if you have a bigger guy and a smaller guy, where that story is just kind of told, from a physical standpoint. It's David vs. Goliath. Which is why our story was pretty easy.

The whole reason for the Hell in a Cell match we had at WrestleMania 32 goes back to a couple of major factors. I had a hiatus from the company for a while prior to that. My three boys had never seen me perform live. They're the main reason I changed my life around, to be more involved in their personal lives. They had asked about me doing it again, and I figured if the right scenario ever came around, I would consider it.

One day, I get a call from my friend Mr. Calaway. He says, "What do you think?" And I ask, "About what?" And he says, "Me and you." My gut was that I didn't want to say no, which stunned me. So I told him to run it by the boss and see what he thought. Taker called Vince. My dad called me. And the rest is history.

The three of us started thinking about this match as a special attraction, and the story was about my comeback after seven years, for control of the company -- which was a great little family dynamic, because you never know with the McMahons what's real and what's not -- and that I'd have to get in there with Vince's chosen representative, and it'll be a Hell in a Cell.

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. You went down a couple of notches in my book." She was scolding me for this moment on the last Monday Night Raw before WrestleMania, when we were going after each other.

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.

I've had many unofficial matches with Mark in hotel rooms, which always ended up in the same result. It's a big-brother/little-brother relationship. Sometimes I'd annoy him. And then other times, he'd just attack me, and I'd have to defend my life. It was hurtful. If it went too far, I'd pick stuff up as an equalizer. I'd swing a lamp at him. It's like a hardcore match, we'd just go at it. I had techniques.

He's a big guy in a small room. There are obstacles. There are two beds. If he finds himself between them, I've got opportunities: I can hit him high, and the bed hits him low. I'm putting covers over him. I'm trying to be as creative as possible, because if he gets free, you're toast. So I'd try to inflict some pain and then find out which way was the door.

I mean, he's so big. What are you going to do?

Once we got to the match itself, there was something so very special and ominous during his ring entrance. The house goes dark. The crowd goes bonkers. Goosebumps 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.

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." So I kicked him in that perfect charley horse spot, and he grunted, and then I knew it was going to be really stiff for the rest of the match. A lot of people will never understand. You're teeing off with your friend. It's like hitting your friend on the arm and then getting one back later.

During the match, I could hear Mark was happy. He's like, "Listen, man, I'm feeling it." The cacophony of sound in that stadium would start way outside and literally like a huge tidal wave that came crashing underneath the ring and then come right up under us. It was powerful. We had so many of those moments in telling the story. Mark said, "We got 'em!" And I said, "Yeah, let's not mess it up."

At one point, I jumped on Taker's back and got him in a rear naked choke. He dove with me through the table. Originally, I thought he was going to pick me up and [throw] me over. Then, when I felt him falling back, I was like, "Oh god, oh god, oh god, oh god," and decided I was just going to hold on. Which ended up being worse. We hit the table, and then I got hit again as his humongous body crushed my rib cage. But again, laughing the whole time. And then we get to the big moment.

He 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 belly button 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.

We knew we had it all the way through the match, just based on the reaction. He was happy with it when it was over.

I always have extra baseball jerseys made for important events, so I presented one to him after the match, and as I was doing that, he was giving me one of his [MMA-style] gloves. That old-school appreciation.

He's in the hardest match of his life right now, because it's against himself. I do understand the limitations of the body, but so much of this is in his head. Even though we sometimes don't want him to be, he is a human being. He does have feelings. He has such respect and love for the business, and specifically the fans, that he never would want to become a cliché. That would be the death blow to him. He wouldn't want an obligatory clap. He wants to earn that adulation.

With "The Last Ride," it's absolutely an honor and a privilege to have the company do this for Mark Calaway. He's absolutely a singular and iconic talent. The character is just awesome, and it has grown with every generation. 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.

There never has been, nor will there ever be, a character like The Undertaker.