Moore attends upstate New York's Stagedoor Manor theater camp, where future beau Zach Braff, Natalie Portman and Robert Downey Jr. also fine-tuned their talents. "She was a quiet, sweet girl," production director Konnie Kittrell tells PEOPLE. Moore often lands solos, but, the director adds, "She wasn't a spotlight seeker."
A Federal Express employee making a delivery overhears 13-year-old Moore singing in an Orlando studio, where she is recording a demo on her own. The deliveryman tells a friend in Sony Music's A&R department, and Moore's demo eventually makes it to the label's Epic 550 Music imprint where she scores a record deal. A freshman, Moore leaves Bishop Moore Catholic High School in Orlando to start working.
Moore hits the road to open for 'N Sync on a sold-out summer concert tour, during which she promotes her hit single "Candy" in anticipation of her debut album. Still a teen, she continues her education with tutors.
Moore releases her first album, So Real, which goes platinum. A year later, some of the tracks are reworked and added with new songs for a more mature sound on her second platinum album I Wanna Be With You.
After landing a Neutrogena contract and hosting Mandy, her daily advice and video show on MTV, Moore meets That '70s Show star Wilmer Valderrama at a photo shoot. The two stars begin dating and breakup in 2002. In 2006, though, Valderrama tells Howard Stern on his radio show that he took Moore's virginity. She responds to the claim in Elle, saying that his remark was "utterly tacky, not even true and it hurt my feelings because I like him."
Moore's mother attends an ATP tennis event where she meets tennis star Andy Roddick and invites him to visit the set of Moore's film How to Deal. "He had a wonderful sense of humor. He was very handsome and tall. That's a big thing for me because I'm almost 5'10, so I need someone tall," the singer recalls to PEOPLE. The two will become a couple in September 2002.
Moore makes her first acting appearance in The Princess Diaries. "I'm the crude popular girl who gets ice cream in her face," she tells In Style. This is actually Moore's second film – she was the voice of a bear cub in the 2001 movie Dr. Doolittle 2, starring Eddie Murphy.
Moore is named one of PEOPLE magazine's 50 Most Beautiful People. The once blond adolescent now dons a darker hue. "They say blondes have more fun, but I felt anonymous," she tells Teen People. "I feel sexy as a brunette."
Moore wins big at the MTV Movie Awards and picks up a trophy for Breakout Female Performance for her role in A Walk to Remember. She plays a pastor's daughter who falls in love with the high school rebel (Shane West). The film grosses $41 million.
Moore stars in Chasing Liberty, as an American president's daughter that runs away with her crush, who happens to be a Secret Service agent. In one scene, her character dives naked into a river, but the bare bottom isn't Moore's. Instead, she selects one from a group of body doubles. "Did I select the one with the best-looking butt? Of course I did. I'm no dummy," she tells The Dallas Morning News.
BIOGRAPHY (top to bottom): COURTESY STAGEDOOR MANOR; Kevin Mazur/WireImage; Lester Cohen/WireImage; Adam Scull/PHOTOLink; Walt Disney/Everett; Frederick M. Brown/Getty; Everett Collection