#5 Drew Carey (2001) - Eliminated 5th - 1 Elimination (Himself)
At the 2001 Royal Rumble, famed TV star Drew Carey was backstage looking to get advice from Vince McMahon on how to promote his show on the PPV system. As Carey was hitting on Trish Stratus, Vince McMahon walked in and decided to punish Carey by putting him in the Royal Rumble match.
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Carey came in at the number 5 spot with Matt and Jeff Hardy battling against each other in the corner. Carey happily watched as the Hardy boys eliminated each other leaving Carey alone in the ring. Unfortunately for Drew, the 6th entrant was Kane who slowly paced his way down to the ring. While Carey did his best to befriend the psychopathic demon and offer him money, Kane grabbed Carey by the throat and was about to pick him up for the chokeslam when Raven, the 7th entry, came to the ring and hit Kane from behind with a Kendo stick.
As Kane busied himself with Raven, Drew Carey was able to eliminate himself from the Royal Rumble. Carey was the first ever celebrity entrant in the Royal Rumble and was later inducted into the WWE Hall of Fame by Kane in 2011.