- 2007: Played a successful writer who returns to his hometown to care for his ailing grandmother (Olympia Dukakis) in Jonathan Kasdan's directorial debut "In the Land of Women"
- 2006: Co-starred in Jason Reitman’s satirical comedy "Thank You for Smoking"
- 2005: Cast opposite Brad Pitt and Angelina Jolie in "Mr. and Mrs. Smith"
- 2003: Made feature debut as a goal-oriented workaholic in the skateboarding comedy "Grind"
- 2003: Starred as the son of Peter Gallagher's character in the Fox television series "The O.C."
- 2002: Had a reoccuring role on the hit television series "Gilmore Girls"
- 2001: Cast as the lead in the MTV cult series "Now What?"
- 2000: Landed the lead in the NBC movie-of-the-week "Growing Up Brady"




