Although his parents made their living in showbiz, his director father and screenwriter mother were cautious when a young Gyllenhaal expressed an interest in acting, forbidding him to take a role in 1992's The Mighty Ducks because it required a long location shoot. Still, the budding thespian played a handful of small roles, sometimes in his parents' projects, before making his leading-man debut in the 1999 family drama October Sky. His breakthrough year was 2001, however, with standout turns in a pair of indie films: a haunted adolescent in the cult classic Donnie Darko and a gawky teen in love with an older woman in Lovely & Amazing, a performance he more or less repeated the next year opposite Jennifer Aniston in The Good Girl. With his brooding intensity and penchant for offbeat characterizations, he quickly established himself as a first-rate actor. Even his starring role in the bloated 2004 action blockbuster The Day After Tomorrow and a two-year, high-profile romance with starlet Kirsten Dunst couldn't tarnish his serious image. In 2005 he continued his streak of thoughtful performances and earned his first Oscar nomination as a gay cowboy in Brokeback Mountain. He followed that sterling, BAFTA-winning performance with turns in Zodiac (2007), Brothers (2009) and Prince of Persia: The Sands of Time (2010). The actor, who also had a two-year romance with actress Reese Witherspoon that ended in 2009, is politically active away from the silver screen, supporting progressive causes, Rock the Vote, the American Civil Liberties Union and environmental initiatives.
- Began acting professionally by the age of 11.
- Parents didn't allow him to take a role in 1992's The Mighty Ducks because it required a two-month location shoot.
- Paul Newman, a family friend, gave him his first driving lesson at age 15.
- Sang in a rock band called Holeshot.
- Auditioned for the role of Christian in Moulin Rouge.
- On-screen sister in Donnie Darko was played by his real sister, Maggie.
- Appeared on the London stage in 2002 opposite Anna Paquin and Hayden Christensen in This Is Our Youth.
- Developed friendships with Brokeback Mountain costars Heath Ledger and Michelle Williams. Is godfather of their daughter, Matilda Rose Ledger.
- In 2006, won the MTV Movie Awards' Best Kiss category with Ledger for Brokeback Mountain.
- Supports Rock the Vote and the American Civil Liberties Union, among other causes.
- 2015, Golden Globe — Best Performance by an Actor in a Motion Picture - Drama: Nominee
- 2006, BAFTA Film Awards — Best Actor in a Supporting Role: Winner
- 2017, BAFTA Film Awards — Best Leading Actor: Nominee
- 2005, Oscar — Best Performance by an Actor in a Supporting Role: Nominee
- 2011, Golden Globe — Best Performance by an Actor in a Motion Picture - Comedy or Musical: Nominee
- 2014, Canadian Screen Awards — Performance by an Actor in a Leading Role: Nominee
- 2015, Independent Spirit Awards — Best First Feature: Winner
- 2015, Independent Spirit Awards — Best Male Lead: Nominee
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- 2006, Critics' Choice Awards — Best Supporting Actor: Nominee
- 2005, Screen Actors Guild Awards — Outstanding Performance by a Male Actor in a Supporting Role: Nominee
- 2014, Screen Actors Guild Awards — Outstanding Performance by a Male Actor in a Leading Role: Nominee
- 2002, Independent Spirit Awards — Best Male Lead: Nominee
- 2015, BAFTA Film Awards — Best Leading Actor: Nominee
- 2017, Critics' Choice Awards — Best Actor: Nominee
- 2005, Screen Actors Guild Awards — Outstanding Performance by a Cast in a Motion Picture: Nominee
- 2013, Critics' Choice Movie Awards — Best Actor in an Action Movie: Nominee
- 2015, Critics' Choice Movie Awards — Best Actor: Nominee
- Reese Witherspoon — Ex-significant Other
- Stephen Gyllenhaal — Father
- Kirsten Dunst — Ex-significant Other
- Maggie Gyllenhaal — Sister
- Naomi Foner — Mother
- Ramona Sarsgaard — Niece
- Jamie Lee Curtis — Godparent
- Matlida Rose Ledger — Godchild
- Kathleen Man — Stepmother
- Alyssa Miller — Ex-significant Other
- Taylor Swift — Ex-significant Other
- Attended Columbia University, New York, New York, United States