Though this writer may be more tolerant of Drew Carey's 2001 Royal Rumble appearance, that does not effect his placement on this list. Carey was a hugely successful comedian-turned-television star and was hosting his first improv pay-per-view. To help promote it, he appeared at the Rumble, meeting Vince McMahon backstage, as well as a handful of Superstars and Divas, including Trish Stratus. It was his encounter with the blonde bombshell, and McMahon mistress, that doomed Carey to the 30-man match. Goaded into competing by Stratus and McMahon, he entered the match at No. 5 and watched as The Hardy Boyz eliminated each other. No one was there to save him as the pyro exploded and Kane stalked toward the squared circle. Carey yanked out a handful of cash and tried to pay his way to safety, but the Big Red Monster was having none of it. He grabbed hold of Carey's throat, teasing a chokeslam, but Raven made the save. Never a stupid man, he eliminated himself and never again entered the Royal Rumble. Much to the delight of historians.