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The Detroit teenager who whispered where everyone else belted, and with Timbaland and Missy Elliott bent R&B toward the future. Aaliyah went from "Back & Forth" at 15 to "Try Again," the first song to top the Hot 100 on airplay alone, and died in a plane crash in August 2001 at 22, five weeks after her third album came out.
The braids, the UPN sitcom, the glass slipper, and the duet that spent thirteen weeks at number one. Brandy was a star at 15 with "I Wanna Be Down," carried Moesha for six seasons, played television's first Black Cinderella in 1997, and with Monica turned a made-up rivalry into "The Boy Is Mine," the best-selling single of 1998.
Lizzie McGuire on TV, platinum pop star on the radio, and the face on every 2003 tween's binder. Hilary Duff was the blueprint Disney Channel superstar, running the show-to-albums-to-movies pipeline that a whole generation of stars followed.
A classically trained dancer from Canada who became the scream queen of the '90s. Party of Five made her a household name; The Craft proved she could anchor a cult phenomenon. By Scream 3, Sidney Prescott was her definitive role—the rare horror heroine who could carry an entire franchise. In the 2000s, she stepped back to pursue her own creative vision.
The teenager with a critic's favorite first kiss who grew into the 2000s' defining star. Southern charm and comic precision built through the '90s—Fear, Freeway, Election—but then Legally Blonde detonated, and she owned the decade. Walk the Line proved she could do Oscar-worthy dramatic work. Married and divorced Ryan Phillippe in a trajectory as public as her career was inescapable.
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.
The dark-eyed patron saint of Gen X — Beetlejuice's goth kid, Heathers' reluctant mean girl, Reality Bites' adrift twentysomething. From 1988 to 1999 Winona Ryder was in seemingly every movie that mattered to anyone under 30, collecting two Oscar nominations along the way.