#2 Ric Flair
A 16 time World Champion, although at least 25 by his own count, Ric Flair is arguably the greatest performer in the history of the industry.
Following the closure of WCW in 2001, Ric would return to WWE at the end of the year, as an on-screen authority figure, manager, and part-time wrestler. The run would last for over 6 years before he retired in 2008, having his last WWE match with Shawn Michaels at WrestleMania XXIV, and a memorable retirement send-off on RAW the following night.
Ric came out of retirement in late 2009, where he had four matches with Hulk Hogan during a tour of Australia with Hogan's short-lived independent promotion, HULKAMANIA. Flair would then sign with TNA Wrestling and debuted on the company's first Impact show of 2010.
Ric would work for TNA for just over 2 years, where he would wrestle 11 more matches. Ric's final match occurred on the September 15 episode of Impact Wrestling, with a very fitting final opponent, Sting. During the match, Flair tore his left triceps on a superplex spot, sidelining him indefinitely from in-ring action.
Flair announced he has officially retired again in late 2012. He cited Jerry Lawler's real-life heart attack on RAW as the reason why.