10 items
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 sharp, seductive update of Laclos' 1782 novel Les Liaisons dangereuses transplanted to Manhattan's prep-school elite, starring Sarah Michelle Gellar and Ryan Phillippe. Written and directed by Roger Kumble, it became a defining late-90s teen drama with genuine cultural impact.
Son of the 1970s sitcom legend Freddie Prinze, who died when Freddie Jr. was a baby. He grew up carrying one of television's most poignant legacies—and then became the face of the late-90s teen-movie boom. Dimpled, kind-eyed, and impossibly likable, he was THE heartthrob of an era that believed in nice guys.
Born 1981, she was the teen-Shakespeare queen of the late 90s and early 2000s—flinty and wry where others were bubbly, older-souled than the wave around her. From Kat Stratford's taming to Ophelia to Desdemona to a ballerina's breakthrough, she was the thinking kid's teen-movie star.
Written by guitarist Matt Slocum and sung by Leigh Nash, this track from Sixpence None the Richer's 1997 self-titled album went nowhere at first. Everything changed in early 1999 when Miramax picked it for She's All That and it landed on Dawson's Creek's soundtrack the same spring. The song detonated, peaking at No. 2 on the Billboard Hot 100 in May and becoming an instant 90s classic.
America's freckled sweetheart of the mid-2000s — Freaky Friday, Mean Girls, a pop album, and a tabloid spotlight that never switched off. For a few years, Lindsay Lohan was the reigning teen-movie queen.
Tim Blake Nelson's modern Othello, relocated to an elite Southern prep school where basketball replaces Venice's wars. Mekhi Phifer as the only Black student and star athlete, Josh Hartnett as the jealous rival, Julia Stiles as Desdemona. It was made to be released in 1999—but held from the world for two years after Columbine.
The face of the late-90s teen boom: a soap-opera Emmy winner who became Buffy the Vampire Slayer and, in a single year, also starred in two of the era's defining horror hits. For a stretch around the turn of the millennium, Sarah Michelle Gellar was the girl who could stake a vampire, outwit a masked killer, and anchor a cult-favorite TV show all at once.
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.
When the teachers at a sleepy Ohio high school start acting strange, six student misfits figure out the faculty is being taken over by alien parasites — Invasion of the Body Snatchers relocated to sixth period. The cast is absurdly stacked: Elijah Wood and Josh Hartnett versus a teachers' lounge containing Robert Patrick, Salma Hayek, Famke Janssen, and, yes, Jon Stewart.