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 "Bop Gun", a 1994 episode of Homicide: Life on the Street; and in the 1998 comedy Homegrown.The story, which received mixed reviews, 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". 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.
Gyllenhaal later starred in the Touchstone Pictures romantic comedy Bubble Boy, which was loosely based on the story of David Vetter.He continued to gain acclaim for Denis Villeneuve's thrillers Prisoners (2013) and Enemy (2013), and he received nominations for the BAFTA Award for Best Actor in a Leading Role for his roles as a manipulative journalist in Nightcrawler (2014) and a troubled writer in Nocturnal Animals (2016).His highest-grossing release came with the Marvel Cinematic Universe superhero film Spider-Man: Far From Home (2019), in which he played Mysterio.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.
Shortly after the 2006 Academy Awards, Gyllenhaal was invited to join the Academy in recognition of his acting career.