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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 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.
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.