10. Shawn Michaels vs. Chris Jericho – WrestleMania XIX
Many people consider Shawn Michaels the greatest wrestler of all time, but have they seen all of his most classic matches? Without a doubt, there are more than enough to fill a ten-entry list. However, this is what we are working with and so we kick off the list with Michaels’ clash with Chris Jericho at WrestleMania XIX.
Years before their intensely personal rivalry in 2008, Michaels faced Jericho as his return from retirement truly took shape. These two have fantastic chemistry together. Their story resembled a teacher vs. student tale. Jericho was determined to prove he had surpassed his idol.
In Seattle’s Safeco Field, they stole the show at arguably the best WrestleMania ever. There was a ton of parity in this match as Jericho stole many of Michaels’ signature moves. However, the Heartbreak Kid was able to outlast the younger Jericho, winning the match at his first WrestleMania in five years.
9. Shawn Michaels vs. Razor Ramon – SummerSlam 1995
Shawn Michaels and Razor Ramon’s ladder match from WrestleMania X is a legendary match. However, the sequel to this match is often forgotten about. While just barely not as good as the original, Michaels and Razor had the WWF’s best match of 1995 at SummerSlam. To say this match stole the show would be an understatement.
Neither man was allowed to use the ladder as a weapon, resulting in more aerial maneuvers than in the original. The dynamic was different here as Michaels was now a babyface but that just meant the fans got to cheer when Michaels put on his incredible performance. This is worth going out of your way to see even 25 years later.
8. Shawn Michaels vs. Shelton Benjamin – Raw (May 2, 2005)
People have tried to recreate the finish of this match many times but this may still be the best. At the match’s climax, Shelton Benjamin went for a springboard only to be caught with the nastiest Sweet Chin Music of all time. The match certainly peaked at the finish, but the rest of the match was excellent as well.
Benjamin was always someone who was extremely talented in WWE. He would get small pushes here and there but he was never someone the company got behind. However, he showed he was capable of much more with classic matches like this. Benjamin and Michaels’ Raw match remains one of the best matches in the history of the show.
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