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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.
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.
It was a success among its intended teenage audience, cementing Phillippe's ability to play characters that require sex appeal.
Phillippe can also be seen in the Marcy Playground music video "Comin' Up From Behind", which appears on the film's soundtrack.