The Undertaker's 10 Greatest Feuds Of His WWE Career

4. Vs. Shawn Michaels

By this point in Undertaker's career, someone had noticed that he had never been defeated in an encounter at WrestleMania. Sure, there was that one disqualification win over Giant González at WrestleMania due to the use of chloroform, but as they say, a win is a win. In any case, the prospect of "beating The Streak" became worth that of any title match at WrestleMania, and that was an honor desired by none other than Mr. WrestleMania himself, Shawn Michaels. For what it's worth, this was far from the first encounter between the Dead Man and the Heartbreak Kid, but- and this may be an unpopular opinion- their other matches were crap, particularly the first Hell in a Cell. Both men are at their best when they want to win more than anything, but in their encounters during the earliest part of what would come to be known as the Attitude Era, Shawn didn't want to beat the Undertaker so much as survive him per the sniveling heel he was portraying. Great storytelling, sure, but a lousy wrestling match, especially when you know what these two men are capable of. And that's where their WrestleMania XXV feud shone. Rather than running for his life, this time Shawn would take Undertaker head-on, even going so far as to perform the same sort of mind games the Dead Man was so well known for, even donning attire that painted him as Undertaker's opposite number. Where Undertaker represented darkness, evil, and Hell, Michaels represented light, good, and Heaven, and the clash between these two opposites was nothing short of- and we know this word gets thrown around a lot, but it really fits here- epic. https://www.youtube.com/watch?v=BK2jG4aoIDg It would not end with WrestleMania, however. Undertaker's victory over Shawn Michaels sent the latter on a downward spiral, at first leaving WWE until his friend Triple H beckoned him back to reform D-Generation X against The Legacy at SummerSlam, and then when Michaels became obsessed with defeating Undertaker to the point he would risk his own career for one more chance to beat The Streak. In the end, Shawn's obsession would become his undoing. Another classic for the ages later, and Shawn Michaels, WWE Superstar, was no more.