The Undertaker: Ranking his top 5 WWE career rivalries

#1 Shawn Michaels vs The Undertaker

One of many classic moments from this instant classic of a match. #WrestleMania▶️ https://t.co/ZDZeOcMbvP pic.twitter.com/aWrqCKl0OL

— WWE Network (@WWENetwork) March 22, 2020

It is rare that a pair of performers find the sort of chemistry that The Undertaker had with Shawn Michaels. Whenever The Undertaker stepped into the ring with The Heartbreak Kid, it became a given that magic was about to unfold.

One of their first pay-pay-view encounters took place in the inaugural Hell In A Cell match at Badd Blood: In Your House in October 1997. An instant classic of a match, the bout was also notable for the debut of Kane. The entire package was near perfect.

However, this match was somehow bettered when The Undertaker and Michaels met at WrestleMania 25 in 2009. Speaking to Ariel Helwani about the bout, The Undertaker confirmed that he felt it was his finest ever work:

"Wrestling is about telling stories. It's a violent, physical way of doing it, but that's the essence of what we do, done right. I'll put the first WrestleMania match with Shawn up against any and say 'show me something that's better than that as far as storytelling and execution.' Follow that up with Shawn's last match. That's some pressure. That's somebody that I feel, personally, and I think most people do, as one of the greatest in-ring, out-of-ring performers ever,"

So well-received was the match, that WWE opted to repeat the formula the following year. This time, though, the bout would serve as the main event of WrestleMania 26 - with Michaels' career on the line if he lost.

The #Undertaker's @WrestleMania showdowns with @TripleH and @ShawnMichaels cannot be denied. #BrokenSkullSessions @steveaustinBSR pic.twitter.com/59PWGHkwL3

— WWE Network (@WWENetwork) November 26, 2019

Michaels did, of course, lose the match. In doing so, yet another layer of story was added to his rivalry with The Undertaker. The Deadman has had a magnificent career, but few of his feuds measured up to the quality of his work with Shawn Michaels.