Raised in Dallas, Texas

Became interested in acting after taking a class in college

Co-starred with brother Owen in the short "Bottle Rocket"; directed by Wes Anderson

Made feature acting debut in full length version of Anderson's "Bottle Rocket"

Had supporting role of Calista Flockhart's co-worker in "Telling Lies in America"

Made a cameo appearance in the film-within-the-film of "Scream 2"

TV acting debut as a sheriff in an episode of "The X-Files" (FOX)

Appeared in back-to-back romantic films opposite Drew Barrymore, "Best Men" and "Home Fries"

Played the doctor beau of a schoolteacher in "Rushmore"; directed by Anderson and co-written by brother Owen

First leading role in the comedy "Dog Park" (released theatrically in 2001)

Was featured in the Sundance-screened comedy "Kill the Man"

Appeared in the sleeper hit "My Dog Skip"

Featured as Cameron Diaz's love interest in "Charlie's Angels"

Cast as Reese Witherspoon's romantic interest in the comedy hit "Legally Blonde"

Co-starred in Anderson's "The Royal Tenenbaums" as a troubled tennis prodigy; also co-starred brother Owen

Made rare TV appearance as Ashton Kutchner's older brother in "That '70s Show" (FOX)

Reprised role for the sequel "Charlie's Angels: Full Throttle"

Again played Emmett in "Legally Blonde 2: Red, White and Blonde"

Acted alongside Vince Vaughn and Will Ferrell in the frat house comedy "Old School"; directed by Todd Phillips

Cast as Orville Wright in the Disney live action feature "Around the World in 80 Days"; also co-starred Owen

Played the slacker brother of Dermot Mulroney's character in the holiday comedy "The Family Stone"

Starred as a regular guy who dumps his superhero girlfriend in Ivan Reitman's comedy "My Super Ex-Girlfriend"

Portrayed an especially ordinary serviceman who is chosen for a cryogenics project in Mike Judge's "Idiocracy"

Co-starred with Kate Beckinsale in the horror film, "Vacancy"

Co-directed with brother Andrew and played the title character in "The Wendell Baker Story"; also wrote and co-starred brother Owen

Starred in Mark Pellington's "Henry Poole is Here"