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Macy, opened on March 18, 2011, Phillippe next filmed the dramatic dark comedy Revenge for Jolly!
, alongside Elijah Wood, Kristen Wiig and Adam Brody, in the summer of 2011.
Phillippe's acting career began after being signed to Cathy Parker Management in Voorhees, New Jersey.
Shortly after, he made an appearance in the ABC daytime drama One Life to Live.
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.
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He has since commented that he believes Cooper to be "the best actor America has to offer".
He then starred in Chaos, in which he plays a police officer, Five Fingers, a drama set in Morocco, Kimberly Peirce's Iraq war film Stop-Loss, and the futuristic Franklyn.