Shawn Michaels and The Undertaker put on some all-time classics inside the ring back in the 1990s. Unfortunately the same could not be said for their backstage interactions, as both men have admitted in interviews. Michaels recently sat down with ESPN as part of the promotion for the Undertaker: The Last Ride documentary series, in which he described what their working relationship was like.
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“I think in some ways, when we were younger, we were frustrated because we had so much unbelievable natural chemistry in the ring with each other, and had zero of it outside the ring,” Michaels said. “At the time, I was an extremely difficult person. He was less so. There was clearly never any real trouble between the two of us. We just did not care for one another because we were so different. He clearly didn’t like me based on who I was and my reputation. And I didn’t like him based on who he was.”
“He never once raised his voice or hit somebody,” Michaels later added. “It bugged me the wrong way. Because he didn’t go and tape his fists. But he didn’t go and make theatrics out of anything. Any time he’d do anything it was very calm, and actually a pleasant conversation. Which was diametrically opposed to the gimmick, so to speak, behind the scenes,” Michaels said. “My immaturity at the time didn’t allow me to grasp that he had it from a respect standpoint. He did it by example. That’s the way it’s supposed to be done. But as I’ve been apologizing for damn near 30 years for everything, I didn’t have the ability to appreciate that when I was younger.”
He explained that his personality and his relationship with “The Deadman” changed for the better once he came back to the company in 2002.
“When I came back in 2002, he was one of the first guys I went to just to apologize for all of my actions in the past. And he was good with it, but at the same time he made it pretty clear: ‘We’ll see.’ I had a reputation,” Michaels said. “A lot of people weren’t sure that [my change] was real. Then of course he recognized how [sorry] I very much was,” Michaels said. “When we got to do the WrestleMania stuff, the bond just got thicker and much deeper. We had both changed and grown in a lot of ways. And when we got in the ring, that chemistry was just so dynamic.”
In the latest episode of The Last Ride, Undertaker admitted he was jealous of how Michaels was able to retire so easily after WrestleMania XXVI.
“I’m so envious of Shawn because he was able to walk away and be…he was good with it. Do I wish I had that kind of clarity? Absolutely,” Undertaker said. “He had the clarity before going into the match. Hopefully, when I have the match I’m looking for, I have that clarity. ‘Okay, that’s it.’”
