Starred in Baltasar Kormákur's action drama "Everest."
Starred in Antoine Fuqua's boxing drama "Southpaw."
Garnered major critical acclaim for his starring role in the drama "Nightcrawler."
Starred in "Prisoners" with Hugh Jackman
Cast opposite Michael Peña in cop drama "End of Watch"
Starred in action thriller "Source Code"
Co-starred with Anne Hathaway in Edward Zwick's "Love and Other Drugs"
Played the lead character Dastan in "Prince of Persia: The Sands of Time"
Co-starred with Tobey Maguire in Jim Sheridan's remake of "Brothers"
Portrayed San Francisco Chronicle reporter Robert Graysmith in David Fincher's serial killer thriller "Zodiac"
Made hosting debut on "Saturday Night Live" (NBC)
Played a CIA analyst opposite Meryl Streep, Alan Arkin, and Reese Witherspoon in "Rendition"
Co-starred with Gwyneth Paltrow and Anthony Hopkins in "Proof," the film adaptation of David Auburn's play; directed by John Madden
Co-starred with Heath Ledger as young men who meet as sheep herders and embark upon a 30-year romantic and sexual relationship in Ang Lee's "Brokeback Mountain"; earned Oscar and SAG nominations for Best Supporting Actor
Portrayed Marine Anthony Swofford in Sam Mendes' "Jarhead," based on Swofford's 2003 Gulf War memoir
Co-starred with Dennis Quaid in Roland Emmerich's blockbuster "The Day After Tomorrow"
Made London stage debut in Kenneth Lonergan's revival of "This Is Our Youth"
Played a young man coping with the death of his fiancée and the grief of her parents in "Moonlight Mile"
Starred opposite Jennifer Aniston in "The Good Girl"
Starred in cult favorite "Donnie Darko"; also co-starred sister Maggie Gyllenhaal
Played the title role in "Bubble Boy," about a young man born without an immune system and has lived his life inside a plastic bubble
Played Catherine Keener's love interest in "Lovely & Amazing"
Made starring debut in "October Sky" as a young man striving to win a science scholarship to avoid becoming a coal miner; film based on Joe Johnston's 1999 adaptation of the Homer Hickam autobiography Rocket Boys
Again directed by his father in the feature "Homegrown"
Appeared on an episode of "Homicide: Life on the Street" (NBC) as Robin Williams' son; episode was directed by his father Stephen
Featured in the children's adventure film "Josh and S.A.M."
Landed small role in "A Dangerous Woman," directed by his father Stephen Gyllenhaal and scripted by his mother Naomi Foner