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In the 2000s, he appeared in several films, including Gosford Park (2001), Crash (2004), and war drama Flags of Our Fathers (2006), Breach (2007), and Stop-Loss (2008).
In 2010, Phillippe starred as Pulitzer Prize-winning photographer Greg Marinovich in The Bang-Bang Club.
December 2010 - February 2011Back when Ryan Phillippe was linked with Amanda Seyfried, he was rumored to also have a short fling (hookup) with Rihanna.
His character Billy Douglas, whom he played from 1992 to 1993, was the first gay teenager on a daytime soap opera.After leaving the show, Phillippe moved to Los Angeles, where he appeared in a number of small parts in various television series including Matlock, Due South, the TV miniseries The Secrets of Lake Success, and movies, including the 1995 film Crimson Tide and the 1996 film White Squall.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.When reports surfaced last year that her then-boyfriend Orlando Bloom was dating Selena Gomez, Perry attempted to shut down the chatter by redirecting fans to news of Bloom’s charitable work for UNICEF. After appearing as Billy Douglas on the soap opera One Life to Live, he came to fame in the late 1990s with starring roles in a string of films, including I Know What You Did Last Summer, Cruel Intentions, and 54.