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.
Along with their mother, Jake and Maggie appeared in two episodes of Molto Mario, an Italian cooking show on the Food Network. Gyllenhaal graduated from the Harvard-Westlake School in Los Angeles in 1998, then attended Columbia University, where his sister was a senior and from which his mother had graduated, to study Eastern religions and philosophy.
Gyllenhaal later starred in the Touchstone Pictures romantic comedy Bubble Boy, which was loosely based on the story of David Vetter.
The film portrays the title character's adventures as he pursues the love of his life before she marries the wrong man.
The film earned million and was described in the Sacramento News and Review as Gyllenhaal's "breakout performance".
Directed by Richard Kelly, the film is set in 1988 and stars Gyllenhaal as a troubled teenager who experiences visions of a 6-foot (1.8 m) tall rabbit named Frank who tells him that the world is coming to an end.
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 "barmitzvah-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.
Actress Maggie Gyllenhaal, his older sister, appeared with him in the film Donnie Darko.
Gyllenhaal expressed mixed feelings about the experience of being directed by Ang Lee in Brokeback Mountain but generally had more praise than criticism for Lee's directing style.
While complaining of the way Lee tended to disconnect from his actors once filming began, Gyllenhaal praised his encouraging direction of the actors and sensitive approach to the material. I've never really been attracted to men sexually, but I don't think I would be afraid of it if it happened. The following year, Gyllenhaal played the lead role in the movie adaptation of the video game Prince of Persia: The Sands of Time, produced by Jerry Bruckheimer and released by Disney on May 28, 2010, and in the romantic comedy Love & Other Drugs, released on November 24, 2010, for which he received a Golden Globe Award nomination.
“How many times in your life have you really been in love – really in love? “Three times,” Gyllenhaal replied, before hedging a bit and adding: “Twice.” He didn’t name names – the actor has dated a number of stars, including Kirsten Dunst, Reese Witherspoon, Taylor Swift and Alyssa Miller – but placed the blame on himself for relationships failing even when he was in love. “I think I probably just got scared.” Gyllenhaal added that he’s not in love at the moment, and he admitted he’s a little sad about that. But at the same time, if you find the right person … I believe in when you meet somebody who’s right, it will be right, and you’ll stay there.” Despite his own commitment issues, Gyllenhaal said he does have role models in that department: his sister Maggie and her husband Peter Sarsgaard, who’ve been married since 2009 and have two daughters. They’re definitely a standard for me,” Gyllenhaal said.
But I also think at some point, you just decide to grow up, you know?
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.