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Would a high school hacker who calls herself "Acid Burn" bother with long, flowing tresses? Well, if she did, she wouldn't look as badass as Jolie does with her severe pixie cut in this movie. This is the moment when the world started coveting that bone structure.
Watch Hackers on Netflix.
Playing By Heart (1998)
Jolie clearly shot her part in this movie in the middle of growing out her Hackers pixie. Oh, girl, we have been there. A quirky red die job (to match love interest Ryan Phillippe's green hair) doesn't completely cover up the awkwardness of that in-between length. Still, even critics who hated this all-these-love-stories-are-connected movie really loved Jolie in it. The film proved early on that she could have sex appeal with a paper bag over her head.
Watch on Playing By Heart Netflix.
To play '70s and '80s supermodel Gia Carangi, Jolie did get to sport some glamorous, cover girl looks. Although, because this HBO movie is also about Gia's descent into drug addiction and AIDS-related death, she also wears her share of awful hairstyles that we hope remain forever locked away.
Watch Gia on HBO.
Girl, Interrupted (1999)
Of course, it took more than frizzy blonde hair with absurdly short bangs to earn Jolie her Best Supporting Actress Oscar as sociopathic mean girl Lisa. Then again, we're sure that it helped her feel crazy.
Watch on Girl, Interrupted Amazon.
Gone in 60 Seconds (2000)
Now, why did Jolie need these raggedy yellow white-girl dreads to play a car thief? We assume the logic comes from the same source that determined it was believable for her to be Nicolas Cage's love interest.
Watch Gone in 60 Seconds on Amazon.