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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.
Phillippe has said that the film was the "best experience" of his career because of its "personal meaning" to him, Phillippe's next role was in the thriller Breach, in which he played FBI investigator Eric O'Neill opposite Chris Cooper.
Shortly after, he made an appearance in the ABC daytime drama One Life to Live.
His character Billy Douglas, whom he played from 1992 to 1993, was the first gay teenager on a daytime soap opera.
She also won the Australian Film Institute: Young Actor’s Award.
- Phillippe accompanied Cornish to the 2008 Australian in Film Breakthrough Awards.