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A witty modernization of Shakespeare's The Taming of the Shrew transplanted to a Seattle-area high school, starring Julia Stiles and Heath Ledger. A modest hit in theaters, it grew into a generational classic and launched the breakout careers of its three young leads.
A 13-year-old wishes herself "thirty and flirty and thriving" in 1987 and wakes up in 2004 as a magazine editor with no memory of the years between. Jennifer Garner's charm — and one glorious "Thriller" dance — turned it into a millennial comfort classic.
A romantic comedy built on a very 2002 premise: a heartbroken San Francisco web designer swears off all sexual contact for the 40 days of Lent — right as he meets the perfect woman. Josh Hartnett at the peak of his heartthrob moment, opposite Shannyn Sossamon.
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 megawatt smile that owned the 90s box office. From Pretty Woman through Notting Hill and Runaway Bride, Julia Roberts was the romantic-comedy lead every studio wanted and every video store shelved face-out — then she capped the run by winning the Oscar as Erin Brockovich.
A modern Pygmalion: class president bets he can turn an art-nerd girl into prom queen in six weeks. Released January 29, 1999, directed by Robert Iscove, it became the surprise smash that crowned the entire late-90s teen-movie wave. A staircase reveal, a perfect song, and one of the era's most-rewatched moments.