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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.Dixon Piper in Mac Gruber, a film based on the Saturday Night Live (SNL) skit of the same name.It was released in the US and Canada on May 21, 2010.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.
In 1999 he starred in Cruel Intentions, a modern retelling of the Choderlos de Laclos novel Les Liaisons Dangereuses, which also starred Phillippe's future wife Reese Witherspoon, as well as his I Know What You Did Last Summer co-star Sarah Michelle Gellar.
In 2010, Phillippe starred as Pulitzer Prize-winning photographer Greg Marinovich in The Bang-Bang Club.
He starred in the lead role of Bob Lee Swagger in the USA Network thriller drama Shooter.
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.
Next up for Phillippe was a rare comedic role as Lt.