- 2007: Portrayed San Francisco Chronicle reporter Robert Graysmith in David Fincher's serial killer thriller "Zodiac"
- 2007: Played a CIA analyst opposite Meryl Streep, Alan Arkin, and Reese Witherspoon in "Rendition"
- 2005: 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
- 2005: Portrayed Marine Anthony Swofford in Sam Mendes' "Jarhead" based on the 2003 book written by Swofford
- 2005: Cast opposite Gwyneth Paltrow in "Proof," the film adaptation of David Auburn's play, directed by John Madden
- 2004: 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"
- 2004: Cohosting the Sundance Film Festival with Zooey Deschanel
- 2002: Appeared opposite Jennifer Aniston in the Sundance-screened "The Good Girl"
- 2002: Starred opposite Dustin Hoffman and Susan Sarandon in "Moonlight Mile"
- 2002: Made London stage acting debut in "This Is Our Youth"
- 2001: Starred in the supernatural teen drama "Donnie Darko"; screened at Sundance
- 2001: Starred in the "Bubble Boy," about a man who was born without an immune system and has lived his life within a plastic bubble
- 1999: Made starring debut in "October Sky", based on Homer Hickham Jr's autobiography "Rocket Boys"
- 1998: Again directed by his father in the feature "Homegrown"
- 1994: Appeared in an episode of "Homicide: Life on the Street", playing Robin Williams' son
- 1993: Had a small role in "A Dangerous Woman", directed by his father Stephen Gyllenhaal and scripted by his mother Naomi Foner
- 1993: Featured in the adventure "Josh and S.A.M."
- 1991: 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




