#2 Shawn Michaels
After retiring Flair, Michaels set his eyes on The Deadman at next year's WrestleMania. The match ended up being regarded as the greatest match in WrestleMania history.
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The following year, Shawn came back for more, demanding another shot at The Undertaker's streak. Taker agreed to a match, with the stipulation being that Shawn would have to retire if he lost again.
After another WrestleMania classic, The Phenom managed to pin The Heart Break Kid, as the sea of fans let out a loud gasp. Shawn Michaels stood in the ring one last time as a performer, as the WWE Universe thanked him for the years of action and entertainment. A tearful Shawn left the ring and went backstage, in possibly the greatest WrestleMania sendoff of all time.
Shawn's retirement was ruined by WWE last year, when he teamed with Triple H in a tag team match against The Undertaker and Kane at Crown Jewel. WWE quickly realized their mistake and HBK is not likely to step foot inside the squared circle again.