Shawn Michaels Q&A: 'It's Been Masterful' to Watch The Undertaker's Evolution Over 30 Years

Shawn Michaels and The Undertaker will forever be linked.

While Michaels is most often connected to Bret Hart, his work with The Undertaker represents some of the most brilliant in-ring displays in WWE history. Michaels and Taker main-evented three pay per views together during a critical five-month period for WWE that spanned from September 1997 to January ’98, which included the first-ever Hell in a Cell match.

Michaels plays a big role in this Sunday’s installment of WWE’s Last Ride documentary. Following Michaels’s return to full-time wrestling in 2002, he put together a string of unforgettable matches against talent that included Chris Jericho, Kurt Angle and Ric Flair. But his most iconic pieces of work were back-to-back masterpieces with The Undertaker at WrestleMania 25 and 26.

Michaels connected with Sports Illustrated to discuss the evolution of his friendship with The Undertaker, covering both the highlights and lowlights together in the ring as well as providing additional detail regarding their work together from the Saudi Arabia show in November 2018.

Courtesy of WWE

Justin Barrasso: The bond between you and The Undertaker took time to develop, especially considering there was never a particular fondness for one another early on during your time together in WWE. Why, initially, was there friction?

Shawn Michaels: At that point in my career, there wasn’t anybody I didn’t have friction with except for Hunter, Nash, Hall and Kid. When Taker first came in [to WWE], he was certainly more of a top guy. He stepped right into a pretty darned decent position, I was building my way up. But as we finally got on the same level, there was really never a particular incident between the two of us that made us decide we didn’t like each other. He didn’t care for me, and honestly, this might sound silly, but my reason for disliking him was because he didn’t like me.

We were polar opposites. He had his segments and I had my segments as we shared a locker room together over the years, but we always had a great deal of respect and admiration for what each other did in the ring. We also always had unbelievable chemistry when we got in the ring together.

I will say this—I can remember a number of years ago, there was an incident when we were in Canada. Me and somebody else were out one night, something went down, and whatever happened ended up pouring outside. It wasn’t going to be good for anybody, but a big ol’ Cadillac came pulling up. Yoko, the Samoans and Taker stepped out, and everybody who was on the opposing side of me scattered. So Taker didn’t like me, but it was another thing altogether for somebody from the outside to mess with me.

It’s well-documented that I gave everybody a reason to dislike me. I just chose to dislike him because he didn’t like me.

Barrasso: I think of the Ground Zero show from September ’97, which had an entertaining no-contest between you and Taker in the main event. During the show, you delivered the memorable line that you’d never rest in peace because you never slept. Especially at this point, even though you’re close in age, were you and Taker just two contrasting personalities?

Michaels: That’s exactly what it was. I was brash and outward and obnoxious, and he wasn’t. Taker led by example. It’s so ironic that we had this dislike for each other outside the ring. We got in the ring and recognized it was so darn easy and special together. There was a chemistry that wasn’t comparable to what we had been doing with a lot of other people, and we both recognized that right away. It’s hard not to admire and enjoy that. So it’s amusing to think that we didn’t care for one another, but we understood that, in the ring, we were really good together.

Barrasso: You had experience in the ring with Taker, but to me, your work together reached a new level in October of ’97 at Badd Blood.

The In Your House pay per views felt like table-setters for the bigger, more established shows, or even shows to fill the gap, but Badd Blood was different. This was you against The Undertaker in WWE’s first-ever Hell in a Cell match. That was also the night when the unexpected death of Brian Pillman was announced.

Do you have any memories of that night? And what were the challenges in preparing for a match you’d never been part of before?

Michaels: That was a very tough day for me personally, for the WWE world, and the locker room with the news of Brian Pillman. So you’re going out there working under that cloud.

Bruce Prichard told us at Gorilla that we were going longer. I looked at Mark and said, “What are we going to do?” And he looked at me and said, “I’ll walk slow.”

So we decided we’d go out there and do what we do. We’d talk to each other and go from there. We had sort of our signpost in the road of where we wanted to go, and we really weren’t sure how we’d get there, but I knew I could bump with him for a while. It was a new match, it was a unique match, so we had that specialness to fall back on. That’s one of those times where we took it to another level because of chemistry.

Barrasso: In terms of story, the match made so much sense. You’d been a problem for The Undertaker since SummerSlam, and he makes you pay with a relentless beating in the Hell in a Cell match. But Kane emerged, interfered, and a bloodied Shawn Michaels won the match and moved on to Survivor Series for a title shot against Bret Hart.

You took the majority of punishment throughout the match. There was such a difference in size and style, and the setting was so unique with the cage. What were you trying to accomplish in terms of in-ring story and psychology?

Michaels: I know people talk about my ego, but back then, that whole “time to get your shine” phrase or mentality just didn’t exist. It was always the bad guy’s job to bounce around and bump. To be perfectly honest, with the dynamic between the Taker and Heartbreak Kid characters, the match did make sense. That’s what I did well and that’s what I enjoyed doing the most.

I make this point now in my teaching and coaching. Yes, I would have looked better had I been more assertive and got myself more “over” in that match instead of just selling. As a good guy, the crowd wanted to see me fight from underneath. But as a bad guy, you’re supposed to let the crowd see you get beat up. Both of those scenarios require vulnerability and you need to have some form of weakness. It took me a long time to grasp it and be centered with it, but that understanding did a lot for me when I came back in 2002. You’re not always supposed to be the number one guy in the match. The match works better when there is a really good number two, so I couldn’t be too strong. The character didn’t lend itself to that. The Heartbreak Kid was meant to be bittersweet.

Barrasso: How did your relationship change with The Undertaker after returning to wrestling in 2002?

Michaels: Taker was one of the first guys I went up to in 2002 and apologized to for my past behavior. His reaction was basically, “Well, I appreciate that, but we’ll wait and see.” All those years later, going into WrestleMania together, was quite fitting.

Barrasso: I’ve always believed WrestleMania 25 was the better match, but nothing can compete with that emotion of WrestleMania 26. Do you have a preference between those two matches?

Michaels: I enjoy 25. It’s always hard to beat that first one. The differences in the match at 26 are what they’re supposed to be, but I don’t think we could ever again capture what we did in the first one. There was so much depth and gravity to that match. The goal at 26 was never to one-up it. The match at 26 was built differently around that bittersweet heartache, which is how it ended when it was all said and done.

Barrasso: We’ve touched on this before, but you opened and closed the WrestleMania 26 match with Taker’s trademark slitting of the throat, designed to capture the spirit and defiance of your career.

Your defiance helped bring you to that moment, but it was The Undertaker—in a business that was the land of the giants when you first started—that shattered your story in the end. Pro wrestling is so often manufactured, but that moment felt organic.

Michaels: It had to be with The Undertaker. And it was the land of the giants. I remember when The Undertaker first came in, and I still marvel at this. I was only a Rocker, but I could hear all the other top guys saying how they didn’t see Taker’s character having the legs to last that long. Certain guys didn’t see a lot of longevity in the no-sell part of it. It’s been masterful to watch what he’s done with that character over 30 years. Pieces of the evolution were at times ever so small, but everything had such great meaning. It’s for all those reasons he had to be the one on the other side of the ring with me. It wouldn’t have meant the same otherwise.

Barrasso: We discussed earlier how Kane first appeared during your Hell in a Cell match with The Undertaker in ‘97. This week’s episode of Last Ride looks at the tag match from the Crown Jewel show that took place in Saudi Arabia in November of 2018. It was you and Triple H against The Undertaker and Kane, your return eight years after WrestleMania 26. Clearly, the match did not meet expectations. Solely as a performer, do you regret the decision to enter the ring one more time with The Undertaker?

Michaels: I have a different view than everybody else. That match in Saudi Arabia, I get it, we can all agree it was a stinkfest. But that was me being selfish, me wanting to be out there with my buddy, be out there again with Taker, and enjoy the moment. That’s why I was able to walk away and not have a problem with it. The performance didn’t go well, but it didn’t bother me.

I wanted to know if I could still do the stuff I once did, and I wanted to go out there with my friends one last time. I will admit that was a selfish thing. I’m so sorry it didn’t go well, so I do have regrets about that part of it. But I will say, and people aren’t going to like this, none of it bothers me in the least.

Barrasso: A driving narrative for the Last Ride documentary has been a build to the conclusion of The Undertaker’s legendary career. How will he know when it is the right time? Or do some never truly know?

Michaels: That’s the million-dollar question. And isn’t it funny? Everybody else always knows when you should stop. Sometimes, you’re the last one to know. But respectfully, that’s your right. That’s all I want from him. I don’t mean to be disrespectful, but I don’t care what anybody else thinks. Mark should do what Mark wants to do. Period. He’s earned it.

Justin Barrasso can be reached at JBarrasso@gmail.com. Follow him on Twitter @JustinBarrasso.