Big Bossman (Ray Traylor), 41
Wrestlemania Record: 5 - 1
Wrestlemania Appearances: WrestleMania V (with Akeem, defeated The Rockers); WrestleMania VI (defeated Akeem); WrestleMania VII (defeated Mr. Perfect via disqualification); WrestleMania VIII (with Virgil, Sgt. Slaughter, Jim Duggan, defeated Nasty Boys, Repo Man and the Mountie); WrestleMania XV (lost to the Undertaker); WrestleMania XVI (with Bull Buchanan, defeated the Godfather and D'Lo Brown)
Career Highlight: It definitely wasn't the time he interrupted a funeral and drove off with the casket. The most beloved prison guard in history debuted in the WWF as the evil henchman of Slick. And in late 1988, Bossman and his tag team partner Akeem the African Dream--a white guy, mind you--feuded with Hulk Hogan and Randy Savage, the two biggest stars in the company.
Date and Cause of Death: Sept. 22, 2004 – Heart Attack