As the offspring of producer/writer Naomi Foner and director Stephen Gyllenhaal, it is not surprising that Jake Gyllenhaal has been acting since childhood. Raised in Los Angeles, Gyllenhaal acted in school plays and made his winsome screen debut when he was in fifth grade, playing Billy Crystal's son in the blockbuster summer comedy City Slickers (1991). Keeping it in the family, while acting with some of the industry's most notable talents, Gyllenhaal subsequently appeared in his parents' adaptation of the novel A Dangerous Woman (1993) with Debra Winger, and played Robin Williams' son in a 1994 episode of TV's Homicide that was directed by his father.

Poised to make the transition from child to adult actor, Gyllenhaal earned rave reviews heralding him as a star-in-the-making for his emotionally sincere performance as real life rocket builder Homer Hickam in the warmly received drama October Sky (1999). Though he opted to stay in school and attend college at Columbia University, Gyllenhaal continued his creative pursuits, playing in a rock band and starring as the oddball title character alongside Drew Barrymore in the Barrymore-produced Sundance Film Festival entrant Donnie Darko (2001). Gyllenhaal could be seen later that same year in multiplexes everywhere as the titular character in Bubble Boy.

After co-starring on the London stage in This Is Our Youth in spring 2002, Gyllenhaal was declared one half of ??Entertainment Weekly?s ?It Gene Pool? (with sister Maggie Gyllenhaal) for his aversion to taking the easy teen flick route. In keeping with his preference for off-center work, Gyllenhaal coincidentally played the younger love object of choice in two consecutive indie comedies, appearing as Catherine Keener?s sensitive boss in Nicole Holofcener?s slyly witty Lovely and Amazing (2002) and Jennifer Aniston?s enticing yet disturbed co-worker in Miguel Arteta?s sardonic The Good Girl (2002). As further proof that he had the acting chops to go with his sad-eyed good looks, Gyllenhaal subsequently co-starred with Dustin Hoffman and Susan Sarandon as a young man enmeshed in his dead fianc饒s family in Moonlight Mile (2002).

--Lucia Bozzola, All Movie Guide