1. Boom! (1968)
The unfortunate star: Elizabeth Taylor
Elizabeth Taylor is held in such high regard by pop culture historians that not even a film as inept as 1968's Boom! can tarnish her legacy, but, alas, that doesn't mean it's any less worthy of contempt. Until the forthcoming Lifetime movie starring Lindsay Lohan as Taylor debuts, this flick is the icon's lowest moment.
Co-starring her then-husband, Richard Burton, Boom! finds a totally unhinged Taylor playing an alcohol-guzzling, forever angry woman living on a far-away island where she rules over a group of tepid servants and secretly worries about her health. It's a showy type of role that can either bring forth multiple awards and/or nominations or simply make the actor involved look humorously, and unintentionally, nutty. Obviously, in Boom!'s case, it's the latter.