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.
Subsequently, Phillippe had supporting parts in the films Igby Goes Down (2002) and Crash (2005), which won the Oscar for Best Picture. In 2006, Phillippe played real-life Navy corpsman John Bradley in the war film Flags of Our Fathers, directed by Clint Eastwood and following the journey of the United States Marines who lifted the flag at the Battle of Iwo Jima.
The movie features Phillippe as an American man who travels to Puerto Rico with his wife (played by Rachelle Lefevre) to adopt an orphan from Haiti.
Next up for Phillippe was a rare comedic role as Lt.
There were no comforts, and I actually appreciate that." He noted that the experience affected him, explaining that "we were shooting during the day in Soweto, and it was an endless procession of funerals—death is so common. It has made me want to get more involved in Africa-based charities." In the summer of 2010, Phillippe began filming the adaptation of popular crime novel The Lincoln Lawyer, taking on the role of Louis Roulet, a wealthy Los Angeles playboy accused of a crime for which his culpability is unclear.
The movie, which also stars Matthew Mc Conaughey, Marisa Tomei and William H.
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.