A longtime friend of the Show, as well as a longtime personal friend of Howard's, Jimmy is perhaps the most famous Stern fanatic around – he even beat out Jerry O'Connell and Jeff Probst to win the Howard Stern Celebrity Superfan Contest in 2008. His show, Jimmy Kimmel Live!, is now entering its 10th year on the air, but Jimmy's first foray into entertainment was actually radio, a move he's said was highly influenced by listening to Howard growing up. His late night talk show has earned Jimmy some very famous friends, all of whom are in attendance whenever Jimmy throws a party and makes Howard the guest of honor. What's great about Kimmel – no matter how high his star rises, his fame never goes to his head. He'll always be a Stern Superfan, and always be welcome on the Show.