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Hilary Duff waits tables at her wicked stepmother's San Fernando Valley diner while trading anonymous messages with a soulmate — who turns out to be Chad Michael Murray, the most popular boy in school. Critics hated it; an entire generation of sleepovers overruled them.
The teen comedy that defined 2000s school social hierarchies — cliques, calculation, and the crushing realization that you might be the problem. Mean Girls premiered in April 2004, written by SNL's Tina Fey, and immediately became the movie every middle and high school student quoted obsessively for the next decade.
Andrew Fleming's cult sleeper hit about four Catholic-school outcasts who form a coven and discover real magic. Featuring Robin Tunney, Fairuza Balk, Neve Campbell, and Rachel True, The Craft codified the 90s goth aesthetic, kicked off the teen-witch wave, and made "We are the weirdos, mister" a quotable rallying cry.
A shy San Francisco teenager discovers she's a princess and gets the makeover of her life—with life lessons in a tiara. Anne Hathaway's breakout film became the ultimate makeover fantasy, complete with Julie Andrews as her regal grandmother.