13. Big Bossman (May 2, 1963 September 22, 2004)
With a career spanning over three decades, Ray Traylor made a name for himself on the wrestling scene by being a huge man who could move like someone much smaller. His most famous character, the Big Bossman, enjoyed a main event run against Hulk Hogan and became one of the WWF's most popular babyfaces afterwards. Former prison guard Ray Traylor started in the Jim Crockett territory as Big Bubba Rogers where he served as Jim Cornette's bodyguard and feuded with the legendary Dusty Rhodes. He moved on to the WWF in 1988 as a heel and became the Big Bossman, an evil prison guard who handcuffed his opponents to the ring ropes and beat them down with his nightstick. A successful feud with Hulk Hogan led to a babyface turn for the newly slimmed down Bossman and he set about dispensing law and order on the WWF. He had a memorable feud with the Heenan Family, culminating with a match against Curt Hennig at Wrestlemania VII. Bossman left the WWF in 1993 for WCW but never found the momentum that he had under Vince McMahon. A number of goofy gimmick changes didn't help matters and soon left the company after losing to Goldberg on Nitro. Surprisingly, Bossman returned to the WWF as a heel and took the role as Vince McMahon's bodyguard in his feud with Steve Austin. Bossman abandoned his trademark blue prison guard outfit for new, all-black SWAT gear. Over time, Bossman became almost a cartoon supervillain, performing dastardly heel actions and then evilly laughing about it. He cooked Al Snow's pet dog and fed it to him, he forced Big Show's mother to admit Show was born out of wedlock, and, most memorably, he crashed Big Show's father's funeral and stole the casket. After 2000, Bossman was mainly relegated to the WWF's B-shows and was jobbed out as his career wound down. Only a few years later, at the age of 41, Ray Traylor died of a massive heart attack, robbing the wrestling world of one of the most talented big men to ever come along.
