5. The Big Boss Man
There wasn't anything overly spectacular about the Big Boss Man, but he more than earned his keep in the major leagues of wrestling. He debuted in the WWF as a pretty big man with a pretty cartoonish gimmick. But unlike the plumbers and the repo men of that era, Boss Man got over. As a heel, he was most well-known for making his opponents serve "hard time", and terrifying young children with his post match beat downs involving a night stick and handcuffs. He was on TV in one of the major companies in one gimmick or another pretty consistently from 1988 until 2002, which may have been why fans started to tire of him. After leaving WCW in 1998, he returned home to the WWF and switched up from his old police man outfit, to a SWAT style one. Most probably thought that Boss Man wouldn't fit in with WWF's Attitude Era, but he made the transition nicely. However, he was cast in some awful storylines that probably contributed to fans no longer wanting to see him a bit sooner than they would have. First, he took part in a flat feud with Undertaker at WrestleMania XV where both were cast as heels. Then he moved on to tricking Al Snow into eating his own dog, and even stole The Big Show's father's casket. Basically, Boss Man jumped the shark. There's really nowhere else to go from a character standpoint after stealing a corpse. Fans no longer booed him, and instead sat on their hands when he came out. Attempts to pair him with Bull Buchanan, Booker T and Mr. Perfect didn't work. Boss Man felt like he was from another time and no matter what kind of nefarious deeds he was up to, people weren't interested. And in wrestling, that's the worst crime of all.