WWE: 10 Most Famous Loser Leaves Town Retirement Matches

5. Ric Flair vs. Shawn Michaels (WrestleMania XXIV)

Ric Flair, ladies and gentlemen. In the latter part of 2007 and continuing into 2008, Ric Flair was facing the challenge of his next loss being his last. Vince McMahon had given him a "win or retire" ultimatum that saw him facing off weekly against men such as Umaga, Triple H, William Regal and even Vince himself in a battle to keep his career alive. When he was booked to face Shawn Michaels at Mania, the story centered around HBK's respect of the Nature Boy and his reluctance to end his idol clashing with Flair's unwillingness to accept that he was ready to be taken out behind the barn. He had a desperate need to prove himself on the grandest stage of them all, and he felt there was no one better to do it against than Mr. WrestleMania. The match was a calvacade of emotions, another classic notch on the belts of two of the greatest performers we'll ever see. It was a heartbreaking moment to see the Showstopper look his hero in the eyes- both men shedding genuine tears-and play Flair into retirement with a little sweet chin music. http://www.youtube.com/watch?v=1zD7ZL1QNRs Now of course, Flair would soon return to the ring for TNA and devolve into a sad self-parody of what he once was, bleeding buckets in front of 230 fans to help pay his outlandish debts, but for that night, it was a fitting end to a brilliant career.