Fail Occurred: October 18, 1991

Despite having the same cinematographer as Schindler's List, Vanilla Ice's star-killing vehicle Cool As Ice did not win any Oscars. In fact, it might be the worst movie ever, a bitter end to Rob Van Winkle's 12-month career death knell. Just as Ice was becoming a music superstar and signing all sorts of crazy multi-picture deals with Hollywood studios, certain contested "facts" about his biography were making him the laughingstock of the music world, even outside of hip-hop. By the time his big-screen debut finally hit theatres (opening at a dismal #17), even his clueless suburban female fans couldn't take his hilariously cheesy James Dean impression seriously.