8. Kelly Osbourne, Chicago
Chicago seems to be a big favorite for celebs looking to break into musical theatre, but unlike many would-be triple threats, Kelly Osbourne didn’t play Roxie in the London production in 2007. She played Big Mama Morton—the role of the jail matron played by Queen Latifah in the movie. Even more shocking, though, was the weight Kelly lost during performance. Alas, I couldn’t find any videos of her performance, but you can check out how dramatically she transformed herself.