Watch Jake Gyllenhaal Online

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.His parents did not allow him to appear in the 1992 film The Mighty Ducks because it would have required him leaving home for two months. In subsequent years, his 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), in a 1994 episode of Homicide: Life on the Street, and in the 1998 comedy Homegrown. Along with their mother, Jake and Maggie appeared in two episodes of Molto Mario, an Italian cooking show on the Food Network. Prior to his senior year in high school, the only other film not directed by his father in which Gyllenhaal was allowed to perform was Josh and S.A.M., a little-known children's adventure.

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. 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, 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."

After the critical success of Donnie Darko, Gyllenhaal's next role was as the lead character in 2002's Highway, a film ignored by audiences and critics alike. His performance was described by one critic as "silly, cliched and straight to video." Gyllenhaal had more success starring opposite Jennifer Aniston in The Good Girl, which premiered at the 2002 Sundance Film Festival; he also starred in Lovely & Amazing with Catherine Keener. In both films he plays an unstable character who begins a reckless affair with an older woman. Gyllenhaal later described these as "teenager in transition" roles.Gyllenhaal later starred in the Touchstone Pictures romantic comedy Bubble Boy, which was loosely based on the story of David Vetter. The film portrays the title character's adventures as he pursues the love of his life before she marries the wrong man.The film was panned by critics, with one calling it an "empty-headed, chaotic, utterly tasteless atrocity".

Following Bubble Boy, 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.

Gyllenhaal was almost cast as Spider-Man for Spider-Man 2 due to director Sam Raimi's concerns about original Spider-Man star Tobey Maguire`s health. Maguire recovered, however, and the sequel was shot without Gyllenhaal. Instead, Gyllenhaal starred in the blockbuster The Day After Tomorrow in 2004, co-starring Dennis Quaid as his father.

In his theatrical debut Gyllenhaal starred on the London stage in Kenneth Lonergan's revival of This is Our Youth. Gyllenhaal said, "Every actor I look up to has done theatre work, so I knew I had to give it a try." The play, which had been a critical sensation on Broadway, ran for eight weeks in London's West End. Gyllenhaal received favorable critical reviews and an Evening Standard Theatre Award in the category "Outstanding Newcomer."

2005 was a prolific year for Gyllenhaal, who starred in the critically praised films Proof, Jarhead, and Brokeback Mountain. 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. 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.

In Brokeback Mountain, Gyllenhaal and Heath Ledger play young men who meet as sheep herders and embark upon a homosexual relationship that begins in the summer of 1963 and continues until the death of Gyllenhaal's character in 1983. The film was often referred to in the media with the shorthand phrase "the gay cowboy movie,"though there was differing opinion on the sexual orientation of the characters. 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. Shortly after the 2006 Academy Awards, Gyllenhaal was invited to join the Academy in recognition of his acting career. Most recently, Gyllenhaal was awarded the 2006 Young Artist Award for Artistic Excellence by The Americans for the Arts National Arts Awards for his role.

Gyllenhaal expressed mixed feelings about the experience of being directed by Ang Lee in Brokeback Mountain, but generally had more praise than criticism for Lee's directing style. While complaining of the way Lee tended to disconnect with his actors once filming began, Gyllenhaal praised his encouraging direction of the actors and sensitive approach to the material. At the Directors Guild of America Awards on January 28, 2006, Gyllenhaal also praised Lee for "his humbleness and his respect for everyone around him."

When asked about his kissing scenes withHeath Ledger in Brokeback Mountain, Gyllenhaal said, "As an actor, I think we need to embrace the times we feel most uncomfortable." When asked about the more intimate scenes with Ledger, Gyllenhaal likened them to "doing a sex scene with a woman I'm not particularly attracted to." Following the release of Brokeback Mountain, rumors circulated regarding the actor's sexual orientation. When asked about such gossip during an interview, Gyllenhaal said:

" You know it's flattering when there's a rumor that says I'm bisexual. It means I can play more kinds of roles. I'm open to whatever people want to call me. I've never really been attracted to men sexually, but I don't think I would be afraid of it if it happened. "

Gyllenhaal narrated the 2005 short animated film The Man Who Walked Between the Towers,based on Mordicai Gerstein's book of the same name about Philippe Petit's famous stunt. In January 2007, as host of Saturday Night Live, he put on a sparkly evening dress and sang "And I Am Telling You I'm Not Going" from the musical Dreamgirls for his opening monologue, dedicating the song to his "unique fan base... the fans of Brokeback."

In 2007, Gyllenhaal starred in David Fincher's Zodiac, which was based on a true story. He played Robert Graysmith, a San Francisco Chronicle cartoonist and author of two books about the Zodiac serial killer. Gyllenhaal stars opposite Meryl Streep, Alan Arkin, and Reese Witherspoon in the October 2007 release Rendition, a Gavin Hood-directed political thriller about the U.S. policy of extraordinary rendition. Gyllenhaal's next roles will be in Jim Sheridan's remake of Susanne Bier's 2004 Danish language film Brothers and Doug Liman's as yet untitled film about the race for lunar colonization. He will also shoot 2009's Nailed in South Carolina, opposite Jessica Biel.

On the show Entourage, Gyllenhaal, though not featured on screen, was the replacement for Vincent Chase in Aquaman 2 after Chase was fired.

On May 20th 2008 it was announced that Gyllenhaal will play the lead role in the movie adaptation of the video game Prince of Persia: Sands of Time, produced by Jerry Bruckheimer. Production is set to start July 2008.