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.
On his 13th birthday, Gyllenhaal performed a "bar mitzvah-like act, without the typical trappings", volunteering at a homeless shelter because his parents wanted to give him a sense of gratitude for his privileged lifestyle.
The film earned million and was described in the Sacramento News and Review as Gyllenhaal's "breakout performance".
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".
Gyllenhaal received favorable critical reviews and an Evening Standard Theatre Award in the category "Outstanding Newcomer". He also auditioned to be Batman for one of the biggest blockbusters, 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.
Following Bubble Boy, Gyllenhaal starred opposite Dustin Hoffman, Susan Sarandon and Ellen Pompeo in Moonlight Mile, as a young man coping with the death of his fiancée and the grief of her parents.