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Phillippe's acting career began after being signed to Cathy Parker Management in Voorhees, New Jersey.

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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.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.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 addition to directing, co-producing, and starring in the film, Phillippe also co-wrote the script with Joe Gossett.

Phillippe has said that the film is based partly on the life experiences of himself and his friends (including the filming of Straight A's in Shreveport in 2011), but is partly meant to be "a fun scary movie in the vein of Misery".

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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 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.