Acting success came quickly for Delaware native Phillippe, who made history when he landed his first role on the soap One Life to Live in 1992: his character, Billy Douglas, was daytime television's first gay adolescent. Although he left the show that same year, Phillippe's star continued to rise, and he cemented his teen idol status in 1997 as one of the attractive ensemble members of the hit horror flick I Know What You Did Last Summer. He also won the heart of future Cruel Intentions costar Reese Witherspoon after meeting 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. Though he and Witherspoon, the parents of two children, split in 2006, the actor has continued to appear in both critically and commercially successful films. He even broadened his range to include comedy with his appearance in the buddy flick MacGruber (2010), which was inspired by a Saturday Night Live sketch.