#1 - Former WWE Superstar & Hall of Famer Ric Flair
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Many believe that Ric Flair is the best wrestler to ever step inside a WWE ring. He is truly a legend, having wrestled in five different decades. The WWE Superstar retired from in-ring action in 2011 when he was sixty-two years old. That shouldn't come as a surprise given that he turned fifty way back in 1999, and was still competing.
Is this man the funniest man in wrestling?
The Nature Boy has certainly left his mark in WWE. During his 50s, Ric Flair held the WCW World Heavyweight Championship, Intercontinental Championship and the Tag Team belts twice.
The WWE Superstar had some remarkable matches during that time period against young up and coming stars, using his knowledge to elevate young talent. His WWE retirement match against Shawn Michaels is considered to be one of the best matches of his career. Ric Flair was fifty-nine years old at the time.
What distinguishes Flair from the rest of the entries on this list is that he was working on a schedule like any other full time wrestler, and didn't let his age show. It simply did not seem to be a factor for The Dirtiest Player in the Game. Furthermore, he wrestled well into fifties and even competed into his sixties, outside of WWE. It was truly remarkable to see Ric Flair creating masterpieces in his 50s with other WWE Superstars during his last run.