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Phillippe can also be seen in the Marcy Playground music video "Comin' Up From Behind", which appears on the film's soundtrack.In the years following, he appeared in the crime drama The Way of the Gun, starred as a famed software engineer in the thriller Antitrust, and co-starred in Robert Altman's Gosford Park, which was nominated for the Oscar for Best Picture.Subsequently, Phillippe had supporting parts in the films Igby Goes Down (2002) and Crash (2005), which won the Oscar for Best Picture. In 2006, Phillippe played real-life Navy corpsman John Bradley in the war film Flags of Our Fathers, directed by Clint Eastwood and following the journey of the United States Marines who lifted the flag at the Battle of Iwo Jima.
After appearing on the soap opera One Life to Live, he came to fame in the late 1990s with starring roles in a string of films, including I Know What You Did Last Summer, Cruel Intentions, and 54.In the 2000s, he appeared in several films, including Gosford Park (2001), Crash (2004), and war drama Flags of Our Fathers (2006), Breach (2007), and Stop-Loss (2008).In 2010, Phillippe starred as Pulitzer Prize-winning photographer Greg Marinovich in The Bang-Bang Club.He was married to actress Reese Witherspoon from 1999 to 2007; together, they have a daughter and a son.He also has a daughter from a relationship with actress Alexis Knapp.
Phillippe's acting career began after being signed to Cathy Parker Management in Voorhees, New Jersey.