Phillips also wrote and directed the 2004 film Starsky & Hutch starring Ben Stiller and Owen Wilson, as well as the 2006 film School for Scoundrels, starring Billy Bob Thornton and Jon Heder. In 2005, Details Magazine cited Judd Apatow, Adam McKay and Phillips as "The Frat Pack". He worked on [[Borat: Cultural Learnings of America for Make Benefit Glorious Nation of Kazakhstan|Borat]] (2006), but he resigned his position as a director in early 2005, due to creative differences. Nevertheless, he was nominated for an Oscar for Best Adapted Screenplay for his role in fashioning the story.
In the meantime, he had a bit role in Steven Spielberg's Empire of the Sun.