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His performance was described by one critic as "silly, cliched and straight to video".
Gyllenhaal later starred in the Touchstone Pictures romantic comedy Bubble Boy, which was loosely based on the story of David Vetter.
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.
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.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 to leave home for two months.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.
Actress Maggie Gyllenhaal, his older sister, appeared with him in the film Donnie Darko.