For a person such as The Undertaker who has had countless spectacular matches, it is hard to point out the ones we can call the best. From a fan’s perspective, we can name some, but now that The Phenom himself has revealed them, we can rest at ease. 

The Undertaker, in his documentary, spoke about the four matches in his career that he is most proud of. Surprisingly enough, only two names made it onto the list, Shawn Michaels and Triple H.

“I have got a lot of moments in my career that I hold very near and dear to my heart and are very special to me with a lot of different guys. But, you know, no disrespect to anybody, I think overall what I’m most proud of as far as matches and storylines and all that, are the four matches that I had. The two with Shawn and the two with Triple H,” Undertaker admits.

Undertaker on Shawn Michaels

Undertaker revealed that he wasn’t very fond of Shawn Michaels in the beginning. However, Michaels’ in-ring work impressed The Deadman so much that it came to a point where he had nothing but respect for The Heartbreak Kid. 

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“It was no secret early on, I was not a big fan of Shawn Michaels. Shawn could rub me the wrong way outside of the ring. I can’t really think of anybody I’d rather work within the ring than Shawn. He’s just that good,” said Undertaker.

Undertaker would wrestle Shawn Michaels at WrestleMania 25 and 26. The former won on both occasions and ended Shawn’s career in their last match-up. However, their performance left fans picking their jaws up off the floor.

“You could feel the electricity. He felt it. I felt it. Everybody felt it,” Undertaker said.

Undertaker even commented on Shawn’s retirement saying he got the John Elway retirement, something that Undertaker hopes for himself.

The end of an era with Triple H and Shawn Michaels

After Undertaker was done feuding with Shawn, WWE decided to let Triple H in. Subsequent WrestleMania events saw Taker wrestle The Game back to back.

The first one was brutal to both the stars and Taker added one more to his streak. When the next match came around, WWE decided to take it up a notch by bringing in Shawn Michaels as the special referee.

The entire length was emotional as they had something personal going on. Shawn would deliver the Sweet Chin Music to Taker to Triple H’s advantage, but Taker kicked out. 

Taker said, “I think right there, more so than any other time ever, did the people think that the streak would be broke.”

The match ended with Undertaker pinning The Game. That matchup marks the finest moment in the WWE universe, to date.

“I knew we had just finished something that was going to be so special that would last through the annuls of time in our industry. It was storytelling at its finest. Here for the last four years, these guys have beat the living hell out of each other. And we did.

“It felt like the end of an era to us and kind of how do we encapsulate that,” claims Taker as he recalls the matchup fondly. 

The three legends would stand on the ramp together, consequently making it one of the biggest fandom moments. 

“It wasn’t an organic moment that happened, it wasn’t planned. It was probably one of the special moments of my career, standing up there with those two guys, who I had the utmost respect for,” Undertaker concluded.