Worked with Hollywood heavyweight Robert DeNiro on This Boy's Life, and costarred alongside Johnny Depp in What's Eating Gilbert Grape, for which he received his first Oscar nomination
Put the finishing touches on her debut album, Sweet Kisses, which included her first hit single, "I Wanna Love You Forever"
Followed up a small role in Endless Love with an even bigger one in the military drama Taps, costarring fellow youngsters Timothy Hutton and Sean Penn
Landed the part of tomboy Joey Potter on the hit teen series Dawson's Creek
Skyrocketed to instant fame with the smash "…Baby One More Time," off the album of the same name
Seen here with dad Jon Voight, kicked off her professional movie career playing a not-quite-human character in the sci-fi sequel Cyborg 2
Tried to revive the movie musical with Disney's Newsies
Became an immediate heartthrob with the success of 'N Sync's debut album and the boy band's hits like "Tearin' Up My Heart" and "I Want You Back"
Flexed both her acting and vocal muscles with a role on the feel-good family drama 7th Heaven and recording a song for the holiday album School's Out! Christmas
Helped make Married With Children wildly popular thanks to her portrayal of bubbleheaded bleach blonde Kelly Bundy…and was rumored to be briefly linked to 26-year-old Brad Pitt!
Won Best Breakthrough Performance at 2004 MTV Movie Awards for Freaky Friday and saw the release of two of her films, Confessions of a Teenage Drama Queen and Mean Girls, that same year
Shot the comedy New York Minute...while managing to squeeze in a little thing called graduation
Was light years away from becoming a fashion icon during her Square Pegs days with costar Amy Linker
Graced the cover of Seventeen magazine and racked up frequent-flyer miles by way of modeling gigs around the world
Were good friends at the High School of Performing Arts in New York. Who knew?
See more stars hustling for their big break Before They Were Fabulous!