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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.
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. 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 joined John Mauceri and David Denby in Adam Gopnik's podium discussion in February 2016 at the David Rubenstein Atrium at Lincoln Center about Leonard Bernstein's breakthrough conducting performance in Carnegie Hall on November 14, 1943; accompanied by Jeanine Tesori on piano, he sang "Maria" from West Side Story.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.Gyllenhaal received further recognition for roles in Zodiac (2007), Brothers (2009), Prince of Persia: The Sands of Time (2010), Love & Other Drugs (2010), for which he was nominated for the Golden Globe Award for Best Actor – Motion Picture Musical or Comedy, Source Code (2011), End of Watch (2012), Prisoners and Enemy (both 2013), Nightcrawler (2014), Southpaw (2015), and Nocturnal Animals (2016), for which he was nominated for the BAFTA Award for Best Actor in a Leading Role.He subsequently appeared in another indie film, The Good Girl (2002) and the climate fiction-disaster film The Day After Tomorrow (2004), portraying a student caught in a cataclysmic climate event.
In 2005, Gyllenhaal portrayed Anthony "Swoff" Swofford in Jarhead, Harold Dobbs in Proof, and Jack Twist in Ang Lee's Brokeback Mountain.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.