Phillippe’s career began with controversy in 1992, when he joined the cast of One Life to Live and played Billy Douglas, the first gay teenager on daytime television. Ahead of its time, Phillippe didn’t last much longer than a year on the ABC soap and headed to Hollywood. In 1997, he starred in I Know What You Did Last Summer, followed by 54 and Cruel Intentions. Phillippe branched out to more mature roles in , and Crash. In 2008, expect Picasso at the Lapin Agile with Jason Biggs, Kevin Kline, Steve Martin, and Elijah Wood. In February 2008, Phillippe appeared in a video supporting Barack Obama's presidential campaign, telling viewers "I think it’s time for a change. I want a better a future for my children.”