- 2008: Starred in Mark Pellington's "Henry Poole is Here"
- 2007: Co-starred with Kate Beckinsale in the horror film, "Vacancy"
- 2007: Co-directed with brother Andrew and played the title character in "The Wendell Baker Story"; also wrote and co-starred brother Owen
- 2006: Starred as a regular guy who dumps his superhero girlfriend in Ivan Reitman's comedy "My Super Ex-Girlfriend"
- 2006: Portrayed an especially ordinary serviceman who is chosen for a cryogenics project in Mike Judge's "Idiocracy"
- 2005: Played the slacker brother of Dermot Mulroney's character in the holiday comedy "The Family Stone"
- 2004: Cast as Orville Wright in the Disney live action feature "Around the World in 80 Days"; also co-starred Owen
- 2003: Reprised role for the sequel "Charlie's Angels: Full Throttle"
- 2003: Acted alongside Vince Vaughn and Will Ferrell in the frat house comedy "Old School"; directed by Todd Phillips
- 2003: Again played Emmett in "Legally Blonde 2: Red, White and Blonde"
- 2002: Made rare TV appearance as Ashton Kutchner's older brother in "That '70s Show" (FOX)
- 2001: Cast as Reese Witherspoon's romantic interest in the comedy hit "Legally Blonde"
- 2001: Co-starred in Anderson's "The Royal Tenenbaums" as a troubled tennis prodigy; also co-starred brother Owen
- 2000: Featured as Cameron Diaz's love interest in "Charlie's Angels"
- 2000: Appeared in the sleeper hit "My Dog Skip"
- 1999: Was featured in the Sundance-screened comedy "Kill the Man"
- 1999: First leading role in the comedy "Dog Park" (released theatrically in 2001)
- 1998: Appeared in back-to-back romantic films opposite Drew Barrymore, "Best Men" and "Home Fries"
- 1998: TV acting debut as a sheriff in an episode of "The X-Files" (FOX)
- 1998: Played the doctor beau of a schoolteacher in "Rushmore"; directed by Anderson and co-written by brother Owen
- 1997: Made a cameo appearance in the film-within-the-film of "Scream 2"
- 1997: Had supporting role of Calista Flockhart's co-worker in "Telling Lies in America"
- 1996: Made feature acting debut in full length version of Anderson's "Bottle Rocket"
- 1992: Co-starred with brother Owen in the short "Bottle Rocket"; directed by Wes Anderson
- Raised in Dallas, Texas
- Became interested in acting after taking a class in college




