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At the age of 17, Ryan Phillippe embarked on a venture that no daytime actor had ever taken on before. Starring as Billy Douglas on One Life to Live, Phillippe played the first gay teenager on a daytime soap. Reflecting on the experience, Phillippe has said “When I auditioned, I had no idea Billy was gay. They told me, and I said ‘Oh! Okay!’ but a shock went through my system. But I realized that maybe this role is where I’m supposed to be.” Phillippe has also commented on the acting skills he gained during Billy’s coming-out scene, which was “the first time ever that I didn’t have to force tears. My voice went all quivery and they flowed out of me.” From daytime drama, the actor went on to star in Cruel Intentions, Crash, and the Oscar nominated Flags of Our Fathers.