Angelina Jolie – 2000 Academy Awards
In 2000, the gorgeous American actress Angelina Jolie was considered the ultimate Hollywood bad girl, so she decided to act accordingly at the Oscars. That same night, she ended up making history by winning an Academy Award and by controversially kissing her older brother, James Haven, on the lips.
Considering Jolie’s statuesque physique, we have to say she’d look great even if she showed up on the red carpet dressed as a banana! Still, Jolie’s 2000 Oscar attire was heavily debated in the press, with many claiming it was excessively black and too trivial for a super-celeb like Jolie.
