To be fair to Elisabetta Canalis, her ex George Clooney is close to the highest a girl can go up the dating chain, and a relationship with him must come with mounds of pressure to look the part of Tinseltown royalty. That probably explains why after two years of dating Clooney, the Italian model jumped ship to a guy who once had his buttcheeks pierced together, Jackass star Steve-O.

However, she isn't the first attractive woman to step out with a man most people would deem unworthy. The following celebrity women also have a history of falling for guys out of their league.