The Undertaker Reveals Which Matches He’s Most Proud of in His Career

During a rare out-of-character interview with Nine Live Apparel, The Undertaker was asked which matches from his history 30-year career he’s most proud of. “The Deadman” had quite a lot to choose from, but eventually he narrowed it down to four — his two WrestleMania matches with Shawn Michaels, his battle with Triple H at WrestleMania XXVII and the Hell in a Cell match at WrestleMania XXVIII.

“I tell you what, WrestleMania 25 with Shawn [Michaels], that’s just one of those matches where everything went the way it was supposed to go. For the most past, I mean. I would’ve been nice to do the dive and land on somebody but other than that lawn dart over the top rope man, that thing was really special,” Undertaker said.

Taker admitted that he and Michaels didn’t get along personally early in their careers, but after Michaels turned his life around the two became close friends.

“So we did 25, then we came back with 26, ‘Streak vs. Career.’ … Talk about pressure, trying to follow 25 with 26,” he added. “And then to come out of those two, it was kind of like a continuation when I did two matches with Triple H. But the whole story kind of went through the four years.”

Taker and Triple H’s WrestleMania XXVII famously ended with “The Phenom” being unable to leave the ring under his own power despite picking up the win. Triple H turned that around the following year to set up another match, only this time inside of Hell in a Cell with Michaels as the referee.

“Those four years were probably the most special, and probably my proudest work in the company.

Undertaker competed at WrestleMania 36 earlier this month in a Boneyard Match. Both the fans and Taker were thrilled with the final result, so much so that he teased the idea of a future Boneyard Match.

“Because that one was so successful it lends to that, but not to give myself a pat on the back, you gotta have the right players to do that,” Undertaker said. “Guys that really understand their characters and really still rely on that part of the business, not just the athletic side of the business. I think more guys kind of lean that way now. Where for me that put me right back in my wheelhouse and AJ can work with a broom handle and put a four star match on.”