Starred in the 1999 film Cruel Intentions with his ex-wife Reese Witherspoon. He also appeared on the soap opera One Life to Live and played the role of Officer Tommy Hansen in the 2004 film, Crash.
He gave memorable performances in the 1997 horror film I Know What You Did Last Summer and in 2000 crime film The Way of the Gun.
He starred alongside Matthew McConaughey in the 2011 thriller, The Lincoln Lawyer.
As a child he earned a black belt in Tae Kwon Do. He was discovered by an agent while getting his hair cut, and soon thereafter debuted as Billy Douglas on ABC's One Life to Live.
He married actress Reese Witherspoon in June 1999, and they separated after 7 years of marriage in October 2007. They had a daughter named Ava Elizabeth Phillippe, who they named after actress Ava Gardner. Their son was named Deacon Reese Phillippe after pitcher Deacon Phillippe, who was Reese Witherspoon's ancestor and played for the Pittsburgh Pirates.