#5 Drew Carey
In 2001, comedian Drew Carey rode high on the success of his wildly popular sitcom, the Drew Carey Show. The program is well known for having outrageous or even downright silly story lines, such as when Drew's secretary drugged him and had him shipped to China.
Much like Jon Stewart, Drew Carey was a big wrestling fan. He was invited to the Royal Rumble as just a special guest, but after a conversation with Vince McMahon, Carey wound up booked into the battle royal himself! When Carey asked if the match was hard, Vince replied that he himself had won it (which was true.)
The insertion of Carey into the Rumble was one of those 'anything can happen' moments in the WWE. Drew Carey came face to face with Kane and tried to bribe his way out of a beat down with cash.
Kane, of course, has no interest in the affairs of mortal currency, and was about to chokeslam the comedian to Hell when Raven inadvertently saved the day. Carey eliminated himself from the match, probably the best decision he'd made all night.
Drew Carey is also a WWE Hall of Famer who was inducted into the celebrity wing of the event.