Worst Oscar Hair Of All Time

worst oscar hairstyle angelina jolie

Angelina Jolie, 2000 Oscars

Angelina Jolie’s talent might’ve blossomed early, but her looks took a while to come in. Her long — and by long I mean looong — stringy hair was in need of a desperate trim (and wash) at the 2000 Oscars. Not only that, but she also dressed in all black, which only added to her witchy appearance. You would think she was accepting an Oscar for her role in the Addams Family. But no, it was for best supporting actress in the film “Girl, Interrupted.”