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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.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.
He was cast in the 1997 horror film, I Know What You Did Last Summer, which co-starred Sarah Michelle Gellar, Freddie Prinze, Jr. The film was a success, and led to Phillippe gaining wider renown and being cast in a few more high-profile films, including 54 in 1998 opposite Neve Campbell, Salma Hayek and Mike Myers.
He starred in the lead role of Bob Lee Swagger in the USA Network thriller drama Shooter.
Phillippe's acting career began after being signed to Cathy Parker Management in Voorhees, New Jersey.
In the 2000s, he appeared in several films, including Gosford Park (2001), Crash (2004), Flags of Our Fathers (2006), Breach (2007), Stop-Loss (2008), Mac Gruber (2010), and The Lincoln Lawyer (2011).