Jake Gyllenhaal made his film debut in City Slickers (1991) and began to establish himself as an up-and-coming actor in such films as October Sky (1999) before being cast in the title role in Donnie Darko (2001), for which he was nominated for an Independent Spirit Award for best actor. Jake Gyllenhaal's performance as a troubled schizophrenic won him excellent reviews and the film quickly acquired cult status. He played opposite Jennifer Aniston in another Sundance favourite in 2002's The Good Girl and once again earned good reviews. Jake Gyllenhaal also starred in the Walt Disney romantic comedy, Bubble Boy. Loosely based on the story of David Vetter, the film portrays the title character's adventure outside the confines of his bubble as he goes after the woman he loves before she marries the wrong man.
Marking his theatre debut, Jake Gyllenhaal appeared on the London stage with a starring role in Kenneth Lonergan's revival of This Is Our Youth. The play, which was a critical sensation on Broadway, ran for eight weeks in London's West End. For his role, Jake Gyllenhaal received an Evening Standard Theatre Award in the category of "Outstanding Newcomer".
Brokeback Mountain (2005), which stars Jake Gyllenhaal, won the coveted Golden Lion at the Venice Film Festival 2005. When asked of his thoughts on playing a character who falls in love with another man, Jake Gyllenhaal showed comfort with his own same-s-- attractions by openly stating every man goes through a period of questioning attractions for other men. However, he later told Details magazine, "I'm open to whatever people want to call me. I've never really been attracted to men s--ually, but I don't think I would be afraid of it if it happened."
Jake Gyllenhaal has an "on-again, off-again" relationship with actress Kirsten Dunst. The two lived together briefly, but continue to appear together in public. Jake Gyllenhaal is friends with Maroon 5 frontman Adam Levine, and the two have known each other since kindergarten.
Jake Gyllenhaal has a German Shepherd named "Atticus" and a Puggle named "Boo Radley" after characters from the novel To Kill a Mockingbird.
Fans of Jake Gyllenhaal refer to themselves as "Gyllenhaalics".