WWE WrestleMania 33: 25 Greatest Moments in WrestleMania History

8. “I’m Sorry… I Love You” (WrestleMania XXIV)

Saying Ric Flair is one of the greatest wrestlers of all time is actually a bit of an understatement. After a 35-year career, everyone knew that his retirement was inevitable at some point. In November 2007, Flair appeared on Raw in Charlotte, admitting he had to retire — but not yet. So Vince McMahon made Flair a deal — he could continue wrestling as long as he kept winning. One loss, and Flair would be forced into retirement.

Flair continued to win for several months, and was named an inductee into the 2008 Hall of Fame. In February, Flair challenged Mr. WrestleMania Shawn Michaels to a match at WrestleMania XXVIV in Orlando. Michaels was reluctant, because he didn’t want to be the one to end Flair’s legendary career. But the match was signed.

The match got under way, and both superstars proved up to the task as they engaged in a series of counters. Flair even taunted HBK with references to Old Yeller — a movie about putting down a beloved, old family pet. Michaels continued to seem hesitant about giving the match his all for fear of being the one to retire The Nature Boy.

Flair capitalized on Michaels’ reluctance several times, but eventually was hit with Sweet Chin Music — but he kicked out. HBK applied a modified figure four, but the dirtiest player in the game used a thumb to the eye to break the hold. Michaels countered a series of Flair chops with another superkick, but didn’t go for a cover.

In one of the more iconic moments in WrestleMania history, Flair staggered to his feet, and Michaels told him, “I’m sorry… I love you,” before delivering a third Sweet Chin Music for a victory. Michaels left the ring quickly, allowing the now-retired Flair to soak in the standing ovation from the crowd and celebrate with his family at ringside.

It’s such a poignant moment, seeing a legendary career come to an end at the biggest event of the year. Definitely one of the top WrestleMania moments in history.