1. Shawn Michaels vs The Undertaker WrestleMania 25
Coming into WrestleMania 25, The Undertaker was 16-0, a multiple time World Champion and a pillar of WWE for nearly 20 years. To win his 17th straight match, he would have to stare down a man who he had never defeated prior to that night in Houston, Shawn Michaels. Additionally, no other opponent was a better challenge than Mr. WrestleMania himself. How do we know this? Shawn said it himselfwho are we to question greatness? The only entity that could hold up to Michaels match quality, was The Streak. At this time, Shawn was a living legend fresh off retiring Ric Flair at WM24. Shawn wrestling a young guy just wouldnt have been right at this point. Having done it all, he looked at The Streak as his final conquest. Unsurprisingly, these men ended up engineering whats considered the greatest match of all-time. Shawn later told his wife he considered retirement immediately because he finally achieved wrestling perfection. While we had seen a ton of false finishes before, this match became the outline for the current era to borrow from. It gave him a reason This match as a spectacle was his greatest performance in either defeat or victory. Shawn showed us all what losing magnificently looked like. These 8 contests were just a snap shot of his brilliance in defeat, as there are many other contests that could be easily swapped out. While many times we can point to superstars victories as career highlights, Shawn is the rare exception to that rule.