For three decades, Calaway has built up his character of the Undertaker into one whose mystique and legend is unmatched in the WWE. A big reason for that success has been Calaway’s penchant for keeping “kayfabe,” which in professional wrestling means presenting the performances as genuine.
Now, after all that time, Calaway, at age 55, is finally letting the fans in on who he is—and the documentary has, after just three episodes, already changed his life.
“It’s taken me a minute to get comfortable opening up. Even in the beginning I was really hesitant. It’s taken me a little while to let the guard down,” Calaway told Newsweek over the phone recently. “I still catch myself at times thinking, ‘Should I say it or not say it?’ I try to make this second nature, which has been a challenge. But I’m really happy with where we’re at and the direction that the doc is going. It’s definitely been a change for me, for sure.”
Because The Last Ride is forcing Calaway to pull back the curtain a bit, that’s precisely what he did in his talk with Newsweek. The wrestling icon talked about how his career has changed over the years, what lies ahead for him and what he thinks is missing from the ring today.
Read our conversation below, and look out for the fourth episode of The Last Ride when it premieres on Sunday, June 14. This interview has been edited for the sake of length and clarity.
There’s a lot going on in the latest episode, and it starts with WrestleMania 35. You don’t have a match, but with the way the Crown Jewel match went down, you could have easily asked for one to redeem yourself. Was that an option at the time?
It came up. I touch on it a little in the doc, but at this point it’s like, do I want to have a match to just have a match? At the time, there wasn’t the right person to build a WrestleMania-worthy angle. I had to look at it—“OK, I don’t want to be on this card just to say I’m on the card.”
One, it’s not going to be what it’s been built to be when you see Undertaker on the card. And two, I felt it was really unfair because if I go on the card, that means someone else won’t be on the card who has been making the rounds all year and working their butts off to try and get on that card. I just felt like it was the right thing to do at the time.
The fourth episode also gets into when you were booked for Starrcast and pulled out. You said your relationship with Vince McMahon changed after that. Can you get into that a little more?
It wasn’t the friendship aspect of it, or the personal feelings for each other. It was definitely business. And the fact that Vince and I are at this point where we rarely have to talk business, especially that kind of business. I believe that caught us both a little bit off guard.
Like I said in the doc, I was oblivious to what’s going on. At the time, I wasn’t really keeping up with what’s going on here and there. And when he called and made me aware of it, it was a no-brainer. I can’t associate myself and I can’t be there. And I understood that. I don’t like committing to things and not being able to fulfill my commitment, either. In this case, it was a no-brainer and I had to pull out of that.
In general we had [Starrcast], and I had some other things lined up and it was more of a misunderstanding in the sense of, “OK, I’m not working that much anymore and now it’s time to capitalize on the brand that I built in outside projects.” So that’s what I did. I finally started a social media account to get out there and work on different opportunities. And WWE at the time wasn’t doing that for me and I didn’t have a problem with that. The way I perceive it, I had my run and there are guys out there working all the time and that’s where your focus is going to be.
We were filming and we didn’t know what we had at that point, as far as the doc was concerned. I was just trying to be a businessman in the sense of trying to earn a living off of other ways other than being in the ring, and Vince, with some of the things that I set up, said I couldn’t do those things without this being in the WWE nest.
The big thing was, there’s nobody working for me on this side of things now. And I’m fine with that and I get it and I’m good. So we had to realize, he had to realize, that now that I’m not in the ring anymore there still needs to be someone to generate interest and get my name out there for outside projects. And once we let our man-pride and egos get out of the way, we were obviously able to sit down and have a productive conversation and he saw my point of view and I saw his point of view, and it was back to business as usual again.
This part of your career is new territory for both of you. Was it easier with Vince after that?
Oh yeah, it was like once we gave our positions and both apologized to each other for the way we treated each other, it was back to like nothing ever happened. It’s been great since and I have people out there looking for opportunities for me and everything was great. It was just a bump in the road. When people say, “Oh, Undertaker and Vince had this falling out”—we did, but it was just one of those things that happen and make a relationship stronger and the friendship stronger, and that’s the way I look at it.
You say that you weren’t involved in the goings-on in the wrestling industry at the time. But what’s your relationship with wrestling like now? Kobe Bryant comes to mind for me as someone who, when they retired, didn’t want to watch basketball for years before he got involved again.
At the time that was happening, I was in the same mindset as Kobe. I needed to take a break and remove myself and find out what else in life was out there. But in preparing for ‘Manias and everything else, I go to Orlando and the Performance Center and I do find that I love to mentor and work with our younger talent.
I’m trying to put some of the toothpaste back in the tube, in the sense of where the product is right now to where it was 10 to 15 years ago. Obviously, the business is evolving and the wrestlers themselves are unbelievably talented and the things they can do is incredible—probably more so than any other time in the business—but there’s an element missing. I think that’s where I can come in and help and give these guys a little different perspective on what they’re doing. I do enjoy it, especially when I go and work with some of these guys and see them apply what we go over in the gym. This is a very difficult business at its easiest, so it takes some guys a very long time for that light switch to go on and figure it out.
When you work with these guys and you see them using the principles you went over with them when you were training, that’s really rewarding for me. I’m sure as we move forward and down the road that I’ll probably have a bigger role with mentoring some of these young guys and gals.
You mentioned an element that’s missing—is it something you can describe or explain?
I think understanding your character and understanding what it is that we actually do.
Right now, there’s a little bit of a disconnect because these guys are so athletically gifted that they rely way too much on that. Guys are climbing up to the top rope and doing a double backflip, laying out someone on the floor and obviously that’s going to get a tremendous pop from your audience, but what happens when you work that way and, as an example, and I really think a lot of this guy, like Drew McIntyre. I’ve seen him in the last three or four times he’s been on TV, and in matches he’s doing the big suicide dive over the top rope. That’s great to have in your repertoire, but you don’t want to do that every single week. For a big guy like that, it’s a pretty impressive move, but if you did that every week, people become desensitized to it and they say, “I’ve seen you do that, now what do you got?”
When I used to do [that move], I was much more judicious. You might get it at WrestleMania, but you won’t get that on TV week after week—it doesn’t become special. That is one example.
So you have to continue to push the envelope to what your physical limitations are and in turn, they don’t get invested in the character, they are invested in seeing what athletic crazy move they’re going to do. That was a part of the success of the Undertaker. People were invested in that character and the good characters through the years, like Stone Cold. Stone Cold didn’t have a huge moveset, it was about his character. He was the anti-establishment, he was a working man’s hero.
Wrestling isn’t about wrestling moves. Wrestling is about telling stories. We use wrestling moves to tell that story and at the end of the day, we’re telling stories of good and evil, this guy did this guy wrong and that’s where you hook your audience. That’s what makes them care, is being able to tell stories. When I work with these guys, yeah, I work on technique and things like that, but I try to tell these guys why you do that and when to do this.
There’s a lot more to it—it just takes a while for guys to figure that out. I think overall that’s the missing point from most of the guys right now. One, they don’t know how to properly tell a story and two, figure out who they are in their ring gimmick.
I remember a time when Superkicks used to finish matches.
Right? The false finishes now—I think that may be a little bit of mine and Shawn’s fault, the way we worked a couple of our matches. But what a lot of people don’t realize is when I let someone kick out of the Tombstone, there’s 20 years of equity in that move where nobody kicked out of it. So when it finally happened it was a big shock. Now it’s commonplace. Nobody’s finish is sacred, and is basically just another move, and they’re making things harder for themselves.
A big part of the fourth episode of The Last Ride delves into your match with Goldberg in Saudi Arabia. Bret Hart infamously called him an unsafe worker, but were you aware of the things said about Goldberg ahead of your match?
Yeah, but nothing that I was worried about. Everybody has some kind of knock on them. I wasn’t worried about that. I’m sure anyone can say that about anyone at any given time. I wasn’t worried about him being “unsafe” before the match.
Have you watched the match back?
I definitely watched it back. It was pretty scary. There’s one aspect to this whole thing that I carry responsibility for. Whenever something happens in a wrestling match, whether someone gets hurt, somebody is dinged up, whatever happens—when I’m working all the time and in my flow, I pride myself to be able to adapt and move to where the situation takes it. I knew he was bleeding, but I was unaware how bad his head was. I was asking him, of course, if he’s OK and he was saying he was, and shaking his head. If I’m in my normal flow of everything and working all the time, I could have altered the match, called a different match. And maybe got around a few things, but it is what it is. It’s unfortunate the way things turned out and that’s the game. You get hurt and things happen. It’s not ballet.
Following your match with Goldberg, you had that tag match with Roman Reigns at Extreme Rules. In the documentary, you tell Vince that’s your last match. We know it’s not your last, but what was your thought process at that moment?
I was really happy from what happened in Saudi with Goldberg to get there. Regardless, I always put everything on my shoulders and because I’ve been around so long, I should be able to fix anything that happens in the ring. Obviously, coming out of that, my confidence is a little rattled and then we had that match in Philly on Extreme Rules and everything felt great.
I had to train like an animal to try and get my body to where it physically was and to get my mind to where it needed to be. It was at the point that, when I pulled Vince aside, it didn’t feel like I could go any further and I was happy. I knew what happened in the tag match and with what happened with Goldberg. I knew that’s where I was at.
It became a recurring thing, but I knew that there was that kind of match left in me. When it happened, I was happy and it was like, “This is it. This is probably when I should walk away.”
I knew I had more in the tank, but I want to leave knowing I had more in the tank. You don’t want to go with nothing left. I couldn’t leave after that Goldberg match. I couldn’t walk away and that being the last memory that I have. It’s a really bizarre and hard game that I play with myself.
Throughout the documentary, you talk about that one match that would be enough for you to walk away. Would a tag match be that? What does that last match look like?
I just want a match that delivered on the build-up and the technical execution to be there, which is the hardest part at this point, because of the physical limitations that I’m at. I’m not playing on the same field as I was, but I still grade myself like I’m in 2003, 2004 and I’m not fair to myself in that aspect.
I want the big moment, the big match and to deliver, and for fans to say, “Yup, he still got it.”
It’s funny because I was just watching The Last Dance and there was a conversation between [Michael] Jordan and Ahmad Rashad in a car and I think they were going to the game. And they were talking about someone and he was like, “They’re going to have to drag me off the court.” I think they were referring to Patrick Ewing. Jordan is like, “I’m not going to be that way. I want people to think I have two or three years left in me and walk away.” I don’t want to go squeaking across the finish line, I want to go full steam ahead and people think I have more races in me.
You want to have that moment, but is it difficult with your limited schedule?
It’s not hard to get through the match. Once I say yes to doing a match at ‘Mania, you have plenty of time for the build. The biggest thing is making sure at this point of my career that I can get myself in the shape that’s needed to have this performance and then to try and figure out the timing. Those are the two hardest things. Third is getting your body conditioned for the trauma that it’s going to take.
That’s the great thing about these guys working all the time—their timing stays sharp. They’re doing it night after night after night, but when you take a year off in between, that becomes difficult. Not only are you dealing with timing, you’re dealing with another year added onto the body, and physically, over time, you can’t do things you once did. So you have to figure out a way to get there and be able to deliver without it looking like you’re not giving it 100 percent.
Your feud with Shawn Michaels and Triple H was four years building on one another. But you don’t have that history with a lot of the guys on the roster. And with your limited schedule, there doesn’t seem like there’s time to build up to that match you’re looking for.
Right, that’s why I have to be very judicious in the opponents I pick. I have to trust and have complete confidence in their ability and where they’re at in their careers, because sometimes it can just be a complete train wreck. It does complicate things when you don’t have that rapport with guys.
There’s only a few more episodes of the documentary left. What do you hope the fans get from the rest of this series?
I want them to understand my love and passion for this business, and to go out and perform for them. I want them to realize that overall, this business is difficult and I know most of our fanbase does, but to have an appreciation for what it takes. These guys do what they do year after year after year and for me specifically, I just want them to understand how I appreciate their support for all these years. And it’s that support on a lot of nights that got me through.
At the tail-end of my career, there were a lot of nights where I went from laying on a trainer’s table and [would] be immobile until it was time to go out there and the fans’ energy helped me through a lot of nights. And I want them to understand I don’t take that lightly, and it’s been one of the pleasures of my life to go out and perform for our audience.
Undertaker: The Last Ride Episode 4 premieres Sunday, June 14 after the Backlash pay-per-view on the WWE Network.
