At the age of eleven, Gyllenhaal made his movie debut in the comedy-drama City Slickers (1991), playing Billy Crystal's character's son.He made an impact in various films in the late 1990s and early 2000s, in films such as the period drama October Sky (1999), his breakthrough performance, and as the title role in the psychological thriller Donnie Darko (2001), for which he received an Independent Spirit Award nomination for Best Actor, playing a psychologically troubled teenager.See more » This movie is great, in my opinion, because its so misunderstood. The dialogue is not heavy, but it is perfectly articulated and emotional, and delivered brilliantly by Jennifer Aniston, who really shines as Justine, a small town girl who wants to get away from the monotony of life.Jake Gyllenhaal's role as a Holden Caulfield wannabe is well pulled off.I particularly liked how depressingly un attractive his drunken dramas were.You could see so many emotions in Justine, trying to ignore what she didn't like about him, trying to find something to love about him.
For his role as Jack Twist, Gyllenhaal 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.
The play was widely-received and played for eight weeks in London's West End.
Gyllenhaal followed his successful theater en devour with a role in Jarhead (2005), playing Anthony "Swoff" Swofford, an aggressive and masculine but equally vulnerable and sensitive Marine during the Gulf War, and Proof (2005), as Gwyneth Paltrow's love interest.
Jacob Benjamin Gyllenhaal was born in Los Angeles, California, to producer/screenwriter Naomi Foner (née Achs) and director Stephen Gyllenhaal.
He is the brother of actress Maggie Gyllenhaal, who played his sister in Donnie Darko (2001). His mother is from a Jewish family, and his father's ancestry includes Swedish, English and Swiss-German.