11. Stewart Pain
Barry Darsow had a very nice career in wrestling. His most famous run was as Smash in the tag team Demolition, but he also managed to get some pretty atrocious gimmicks to respectable levels during his time. After all, this is the man who turned Repo Man into a credible threat. However, the gimmick with a suck he just couldn't overpower was Stewart Pain. Some creative genius sat around trying to come up with ideas for characters and thought what the show needed was an evil golfer. So Darsow grabbed some clubs and tried to make the best of it. The passing of golfer Payne Stewart led to the character's name being changed to Mr. Hole-In-One Barry Darsow (and later "Putting" Barry Darsow) but it made little difference, as this golfer's handicap was an awful gimmick.