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.
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 received favorable critical reviews and an Evening Standard Theatre Award in the category "Outstanding Newcomer". He also auditioned to be Batman for the blockbuster Batman Begins and Heath Ledger play young men who meet as sheep herders and embark upon a sexual relationship that begins in the summer of 1963 and lasts for 20 years.
In 2005, Gyllenhaal starred in the critically praised films Proof, Jarhead, and Brokeback Mountain. 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.
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.
His performance was described by one critic as "silly, cliched and straight to video".
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.