Boasting an angelic face juxtaposed against an intense sexual energy, this pretty-boy actor was still a teen when he landed his debut role on One Life to Live as daytime television's first gay adolescent character. After a handful of TV guest spots and small film roles, Phillippe's career and his life kicked into overdrive in 1997. He made teen girls swoon as one of the attractive ensemble members of the hit horror flick I Know What You Did Last Summer, and he also won the heart of future Cruel Intentions costar Reese Witherspoon when he began courting her at her 21st birthday bash. Like Witherspoon, Phillippe worked diligently to shed his teen-idol image, choosing challenging supporting parts in indies (Gosford Park, Igby Goes Down, the Oscar-winning Crash) as opposed to hollow Hollywood fare, yet his star and his salary didn't rise as fast as hers. But Phillippe didn't seem jealous of her success. In fact, when he and Witherspoon were copresenters at the 2002 Academy Awards, he gestured to the envelope and quipped, "You open it. You make more money than I do." Although cynics insisted that their union wouldn't last, to most they seemed like Hollywood's perfect couple, two down-to-earth people with a pair of gorgeous kids. Then suddenly in October 2006, they announced that they were separating after seven years of marriage, amid rumors of his infidelity.