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Along with their mother, Jake and Maggie appeared in two episodes of Molto Mario, an Italian cooking show on the Food Network. Gyllenhaal graduated from the Harvard-Westlake School in Los Angeles in 1998, then attended Columbia University, where his sister was a senior and from which his mother had graduated, to study Eastern religions and philosophy.
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 the 1993 film Josh and S. Gyllenhaal dropped out after two years to concentrate on acting but has expressed intentions to eventually finish his degree.
Actress Maggie Gyllenhaal, his older sister, appeared with him in the film Donnie Darko.
Gyllenhaal's father, who was raised as a Swedenborgian, is of Swedish and English descent, and is a descendant of the Swedish noble Gyllenhaal family.
Gyllenhaal's performance was well received by critics; Gary Mairs of Culture Vulture wrote 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 Pilot Kelston in 2002's Highway alongside Jared Leto.
In 2005, Gyllenhaal portrayed Anthony "Swoff" Swofford in Jarhead, Harold Dobbs in Proof, and Jack Twist in Ang Lee's Brokeback Mountain.
For his performance in Brokeback Mountain, he received critical acclaim and won the BAFTA Award for Best Actor in a Supporting Role and was nominated for the Screen Actors Guild Award for Outstanding Performance by a Male Actor in a Supporting Role, the Satellite Award for Best Supporting Actor – Motion Picture, and the Academy Award for Best Supporting Actor.
While complaining of the way Lee tended to disconnect from his actors once filming began, Gyllenhaal praised his encouraging direction of the actors and sensitive approach to the material. I've never really been attracted to men sexually, but I don't think I would be afraid of it if it happened. The following year, Gyllenhaal played the lead role in the movie adaptation of the video game Prince of Persia: The Sands of Time, produced by Jerry Bruckheimer and released by Disney on May 28, 2010, and in the romantic comedy Love & Other Drugs, released on November 24, 2010, for which he received a Golden Globe Award nomination.
You know it's flattering when there's a rumor that says I'm bisexual. Gyllenhaal starred opposite Meryl Streep, Alan Arkin and Reese Witherspoon in the October 2007 release Rendition, a Gavin Hood-directed political thriller about the U. The film was released on September 21, 2012 and received positive reviews, with Roger Ebert saying that "End of Watch is one of the best police movies in recent years, a virtuoso fusion of performances and often startling action", and Salon.com's Andrew O'Hehir stating that the film was "at least the best cop movie since James Gray's We Own the Night, and very likely since Antoine Fuqua's memorable Training Day (which, not coincidentally, was written by Ayer)".
His performance was described by one critic as "silly, cliched and straight to video".