Phillippe, 15, makes an impromptu call to an agent recommended to him by a woman at a local barbershop in Delaware. For two years, Phillippe hits auditions in Philadelphia and lands some small modeling jobs.
At 17, Phillippe plays gay teenager Billy Douglas on the ABC soap One Life to Live. The character pushes the limits of daytime television with storylines about coming out and homophobia. "Soaps are a powerful way to reach people who live these sheltered, closed-off lives," Phillippe tells Paper magazine in 2001. He leaves the show in 1992 after disagreements with ABC regarding his character's development and moves to L.A. to pursue a film career.
Phillippe attends Reese Witherspoon's 21st birthday party for the free drinks. At the party, she tells him, "I think you're my birthday present." Both acknowledge an intense initial emotional connection; after five weeks of phone calls, the two go out on their first date.
Phillippe rounds out an ensemble cast that includes Sarah Michelle Gellar, Freddie Prinze Jr. and Jennifer Love Hewitt in the teen thriller I Know What You Did Last Summer. The movie launches him as a heartthrob. Close friend Meyer tells Paper magazine, "When we used to go places, people's heads used to flip for the boy. Seth [Green] and I refer to him as 'The Boy.' He's a pretty boy."
In 54, a drama about the New York nightclub Studio 54, Phillippe plays a bisexual bartender caught up in the heady days of the '70s disco era. Although most of the steamier scenes are cut, the film solidifies Phillippe's reputation as a sex symbol, with Sela Ward's character describing him as having "the body of David and the face of a Botticelli."
Phillippe wants to work with then-girlfriend Witherspoon, asking her to costar in Cruel Intentions, an erotic prep-school version of the French novel Les Liaisons Dangereuses. They do not collaborate on film again. "There's something to be said for the individuality and mystery of doing things on your own," Phillippe tells Interview in 2006.
A summer wedding follows their December engagement, and a six-months-pregnant Witherspoon, 23, and Phillippe, 24, marry on a plantation near Charleston, S.C.
Phillippe and Witherspoon celebrate the birth of their daughter, Ava Elizabeth, named for his grandmother. As a teenager Philippe helped his mother Susan run a day-care center from their home, so he teaches Witherspoon how to change a diaper. "He completely potty-trained Ava by himself," Witherspoon tells PEOPLE in 2003. "He knows exactly how to negotiate a tantrum."
Phillippe takes the lead in The Way of the Gun. Although the film is a commercial flop, the New York Times says, "Mr. Phillippe is the real surprise. His angel-boy face is hidden under wiry scrubs of facial hair, and he uses a runty voice as if he had studied the Dustin Hoffman or Al Pacino of the 1970's." He also takes a small role in Company Man, which also flops.
As Witherspoon nabs runaway successes with Legally Blonde and Sweet Home Alabama, Phillippe quietly takes roles in the indie drama Igby Goes Down and Robert Altman's Oscar-winning ensemble Gosford Park. The New York Times lauds his performance in Igby, recognizing how Phillippe "finds a hint of vulnerability in this cold, condescending smoothie."
BIOGRAPHY (top to bottom): CLASSMATES YEARBOOK ARCHIVES; Steve Granitz/WireImage; James Bridges/Mandalay Entertainment; Interfoto USA/SIPA; Columbia Pictures/Everett; London Entertainment/Splash News; Everett