- 2009: Lent his voice to the animated film, "Battle for Terra"
- 2009: Joined an ensemble cast for the film adaptation of "He's Just Not That Into You"
- 2008: Had a small role in "Zack and Miri Make a Porno"
- 2007: Co-starred with Bruce Willis in "Live Free or Die Hard" the fourth "Die Hard" sequel
- 2007: Voiced Alvin in the animated feature, "Alvin and the Chipmunks"
- 2006: Began appearing as a Mac in Apple Computer's Get a Mac campaign
- 2006: Appeared in the comedy "The Break-Up" opposite Jennifer Aniston
- 2006: First leading role, "Accepted" as a high school student who creates a fake university after being rejected by every University
- 2005: Starred opposite Lindsay Lohan in the Disney feature "Herbie: Fully Loaded"
- 2004: Co-starred with Ben Stiller and Vince Vaughn in the comedy "Dodgeball: A True Underdog Story"
- 2002: Cast opposite Britney Spears in "Crossroads"
- 2001: Featured in the summer camp-set teen comedy "Happy Campers"
- 2001: Starred in the teen thriller "Jeepers Creepers"
- 2000: Was a regular on the popular NBC series "Ed" playing Warren, an awkward lovestruck teen
- 2000: Acted in a production of "Hot l Baltimore" at the Williamstown Theater Festival
- 1999: Played the fan who helps the actors in the cast of "Galaxy Quest" carry out their real-life interplanetary mission
- Was a member of the Vassar College comedy troupe Laughingstock
- Acted in local theater productions in Fairfield, Connecticut




