She appeared alongside Kate Hudson in the musical drama Almost Famous (2000). The film received four Academy Awards nominations and was a critical success but not a box office success. In 2001, she appeared in the comedy Tart and in the drama Bully. Later, Phillips starred in the thriller feature Octane, which was released at the Cannes Film Festival in 2003; in the film, she appeared opposite Mischa Barton. In 2004, Phillips starred opposite Jeff Bridges and Kim Basinger in The Door in the Floor, a film adaptation of John Irving's novel A Widow For One Year. She portrayed a leading role as Emily in the low-budget drama Havoc (2005), alongside Anne Hathaway. That year, she appeared in the teen horror-thriller Venom. She played one of the main characters, Whitney, in the sequel to the horror film Hostel, Hostel: Part II, which opened in 2007. She also starred in What We Do Is Secret, in which she appeared again with Lauren German (her Hostel co-star). She received critical acclaim for her portrayal; Phil Gallo for Variety called Phillips' performance "striking" and stated that her character "lights up in a unique way whenever she's in Crash's company or simply talking about him. "