Made film debut in "City Slickers", playing Billy Crystal's son

Was forbidden by parents to take a role in Disney's popular children's hockey film "The Mighty Ducks" (1992), as the shoot would keep him away from home for two months

Featured in the adventure "Josh and S.A.M."

Had a small role in "A Dangerous Woman", directed by his father Stephen Gyllenhaal and scripted by his mother Naomi Foner

Appeared in an episode of "Homicide: Life on the Street", playing Robin Williams' son

Again directed by his father in the feature "Homegrown"

Made starring debut in "October Sky", based on Homer Hickham Jr's autobiography "Rocket Boys"

Starred in the supernatural teen drama "Donnie Darko"; screened at Sundance

Starred in the "Bubble Boy," about a man who was born without an immune system and has lived his life within a plastic bubble

Starred opposite Dustin Hoffman and Susan Sarandon in "Moonlight Mile"

Appeared opposite Jennifer Aniston in the Sundance-screened "The Good Girl"

Made London stage acting debut in "This Is Our Youth"

Cohosting the Sundance Film Festival with Zooey Deschanel

Starred with Dennis Quaid in Roland Emmerich's dramatic look at the effects of global warming and the next ice age in "The Day After Tomorrow"

Cast opposite Gwyneth Paltrow in "Proof," the film adaptation of David Auburn's play, directed by John Madden

Portrayed Marine Anthony Swofford in Sam Mendes' "Jarhead" based on the 2003 book written by Swofford

Co-starred in the Ang Lee Western "Brokeback Mountain" a raw, powerful love story of two young men than spans over 30 years; earned Oscar and SAG nominations for Best Supporting Actor

Portrayed San Francisco Chronicle reporter Robert Graysmith in David Fincher's serial killer thriller "Zodiac"

Played a CIA analyst opposite Meryl Streep, Alan Arkin, and Reese Witherspoon in "Rendition"