Angelina Jolie

Couldn't have been too hard for Jolie to play a mentally disturbed young girl at a alongside the likes of Winona Ryder considering she was at the peak of her own bizarre fetishes and craziness at the time. The film in question, Girl Interrupted, was a misogynistic foray into the world of the twisted and it won Jolie a Best Supporting Actress Oscar. 

With her stringy blonde bangs, deliciously unpredictable character, multiple tattoos and crazy-eyed look, we have to admit, Jolie has never looked hotter!