In the dark comedy Little Boy Blue, Phillippe co-starred with Natassja Kinski. He also co-starred in Greg Araki's much acclaimed Nowhere, the third in Araki's independent film trilogy. He then starred in the box-office smash I Know What You Did Last Summer and received a 1999 Blockbuster nomination for Best Supporting Actor.
Several starring roles followed for Phillippe, including Homegrown, co-starring Billy Bob Thornton and Hank Azaria; Miramax's 54, co-starring Mike Myers, Selma Hayek, and Neve Campbell; and Playing By Heart, with an ensemble cast including Sean Connery, Gena Rowlands, Angelina Jolie and Dennis Quaid. He also starred opposite Reese Witherspoon and Sarah Michelle Gellar in the box office hit Cruel Intentions, receiving a 2000 MTV Award nomination for Best Male Performance.
Most recently, Phillippe was seen in Robert Altman's Oscar-nominated Gosford Park with an ensemble cast including Kristen Scott Thomas, Maggie Smith, Helen Mirren, and Emily Watson. His other work includes Anti-Trust, co-starring Tim Robbins; Company Man with Sigourney Weaver; and Way of the Gun with Benicio Del Toro and Juliette Lewis.
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