Born in Los Angeles, California

December 19, 1980

Gyllenhaal was born in Los Angeles, California, the son of film director Stephen Gyllenhaal and film producer and screenwriter Naomi Foner (née Achs). Maggie Gyllenhaal, his sister, is also an actor, and played his sister in the movie Donnie Darko. Gyllenhaal's father was raised in the Swedenborgian religion and is a descendant of the Swedish noble Gyllenhaal family. His last native Swedish ancestor was his great-great-grandfather, Anders Leonard Gyllenhaal. Gyllenhaal's mother is from a Jewish family from New York City. Gyllenhaal's Bar Mitzvah celebration took place at a homeless shelter because his parents wanted to instill in him a sense of gratitude for his privileged lifestyle. Gyllenhaal has said that he considers himself "more Jewish than anything else".

City Slickers

June 7, 1991

During childhood, Gyllenhaal had regular exposure to filmmaking due to his family's deep ties to the industry. As an 11-year-old he made his acting debut as Billy Crystal's son in the 1991 comedy film City Slickers.

A Dangerous Woman

December 3, 1993

Gyllenhaal's parents allowed him to audition for parts, but regularly forbade him to take them if he were chosen. He was allowed to appear in his father's films several times. Gyllenhaal appeared in the 1993 film A Dangerous Woman along with sister Maggie.

Graduated Harvard-Westlake School

June 1, 1998

Gyllenhaal graduated from the Harvard-Westlake School in Los Angeles in 1998, then attended Columbia University, where his sister and mother also attended, to study Eastern religions and philosophy. Gyllenhaal dropped out after two years to concentrate on acting, but has expressed intentions to eventually finish his degree.

October Sky

Feburary 19, 1999

Gyllenhaal's first lead role was in October Sky, Joe Johnston's 1999 adaptation of the Homer Hickam autobiography Rocket Boys, in which he portrayed a young man from West Virginia striving to win a science scholarship to avoid becoming a coal miner. The film earned $32 million and was described in the Sacramento News and Review as Gyllenhaal's "breakout performance."

Donnie Darko

October 26, 2001

Donnie Darko, Gyllenhaal's second major film, was not a box office success upon its initial 2001 release, but eventually became a cult favorite. The film, directed by Richard Kelly, is set in 1988 and stars Gyllenhaal as a troubled teenager who, after narrowly escaping death, experiences visions of a 6 foot (1.8 m) tall rabbit named Frank who tells him that the world is coming to an end. Gyllenhaal's performance was well-received by critics; Dan Kois of Salon.com claimed that "Gyllenhaal manages the difficult trick of seeming both blandly normal and profoundly disturbed, often within the same scene."

The Good Girl

August 7, 2002

The film starts with narration about the life of Justine Last (Jennifer Aniston), a sad and lonely 30-year-old woman living in a dusty Texas town in the middle of nowhere. She works at the local Retail Rodeo (a seedy version of Wal-Mart), with Cheryl (Zooey Deschanel), a cynical young girl who inserts subliminal profanities in announcements to the sleepwalking customers; Gwen (Deborah Rush), the overly peppy, older woman who works with Justine in the cosmetics department; and Corny (Mike White), the Bible-obsessed security guard.

one day, a new, young cashier named Holden Worther (Jake Gyllenhaal) starts working at the Retail Rodeo. Holden keeps to himself and always has his nose in a copy of The Catcher in the Rye claiming that his own life parallels that of Holden Caulfield. Justine and Holden start spending a lot of time together, having lunch every day and even hanging out after work.

Kirsten Dunst

September 1, 2002 - August 1, 2005

Jake's most notable relationship has been with actress Kirsten Dunst. Introduced through his sister, the two began dating in September 2002 and were reported to have officially broken up in July 2004; however, the relationship remained off and on up until August 2005.

Moonlight Mile

September 24, 2002

Gyllenhaal starred opposite Dustin Hoffman, Susan Sarandon and Ellen Pompeo in Moonlight Mile, as a young man coping with the death of his fiancée and the grief of her parents. The story, which received mixed reviews, is loosely based on writer/director Brad Silberling's personal experiences following the murder of girlfriend Rebecca Schaeffer.

The Day After Tomorrow

May 28, 2004

Gyllenhaal starred in the blockbuster The Day After Tomorrow in 2004, co-starring Dennis Quaid as his father.

The Day After Tomorrow is a 2004 apocalyptic science-fiction film that depicts the catastrophic effects of global cooling. Worldwide, it is the 45th top grossing film of all time, with total revenue of US $542,771,772. It is the second highest grossing movie not to be #1 in the US box office (behind My Big Fat Greek Wedding). It currently holds the record for biggest opening weekend gross for any movie not opening at #1 with $68.7 million. The movie was filmed mostly in Montreal, and, as of 2008, is the highest grossing Hollywood film in history to be filmed in Canada.

Proof

September 5, 2005

In Proof, featuring Gwyneth Paltrow and Anthony Hopkins, Gyllenhaal played a graduate student in mathematics who tries to convince Paltrow's character to publish a revolutionary proof to a problem puzzling the mathematicians' community.

Jake's a Godfather

October 28, 2005

Gyllenhaal himself is the godfather of Matilda Rose Ledger (born October 28, 2005), daughter of the late Heath Ledger and Michelle Williams, both of whom co-starred with him in Brokeback Mountain.

Jarhead

November 4, 2005

In Jarhead, Gyllenhaal played against his usual "sensitive yet disturbed" type by displaying an aggressive masculinity as a violent U.S. Marine during the first Gulf War. The title comes from the slang term used to refer to Marines (sometimes by Marines themselves).

Brokeback Mountain

December 16, 2005

In Brokeback Mountain, Gyllenhaal and Heath Ledger play young men who meet as sheep herders and embark upon a homosexual relationship that continues through the 1960s and 1970s. The film was often referred to in the media with the shorthand phrase "the gay cowboy movie."

The film won the Golden Lion prize at the Venice Film Festival. The film went on to win four Golden Globe Awards, four British Academy of Film and Television Arts (BAFTA) Awards, and three Academy Awards. Gyllenhaal was nominated for an Academy Award in the category of Best Supporting Actor for his performance, but lost to George Clooney for Syriana. Gyllenhaal also won the Best Supporting Actor BAFTA for the same role and received a Best Supporting Actor nomination and Best Film Ensemble nomination from the Screen Actors Guild. Also for "Brokeback Mountain", he and Ledger won an MTV Movie Award for "Best Kiss" in 2006.

Fire Escape

December 1, 2006

Jake and his sister escaped a fire that destroyed Manka's, a famed lodge and restaurant in Inverness, California, at which they were vacationing.

Reese Witherspoon

October 1, 2007 - Now

Throughout 2007, there was persistent speculation in the mass media about a romantic relationship between Gyllenhaal and his Rendition co-star Reese Witherspoon. The pair denied the rumors while promoting Rendition in the fall of 2007. However, after a trip to Rome and the finalization of Witherspoon's divorce from Ryan Phillippe in October 2007, Gyllenhaal and Witherspoon became more open with their relationship. Therefore they have been seen in public more.