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 the 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' 1993 adaptation of the novel A Dangerous Woman 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 as the titular character in the ill-fated
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 & 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 fiancée’s family in
Moonlight Mile (2002).
With his star on the rise and his status as a heartthrob all but cemented, it became impossible for Gyllenhaal to avoid the draw of a big summer blockbuster. In 2004, he starred alongside
Dennis Quaid in the mega-budgeted
The Day After Tomorrow, and the success of that film put him in another league altogether. What followed was an interesting, challenging mix of roles for the young actor. He could be seen in the fall of 2005 starring in no less than three high-profile prestige films, all of them adaptations: the delayed big-screen version of the Pulitzer-prize winning play
Proof, with
Gwyneth Paltrow; the Gulf War memoir
Jarhead, directed by
American Beauty wunderkind
Sam Mendes; and
Ang Lee's cowboy romance
Brokeback Mountain. The first two films received an indifferent response by critics, even though
Jarhead's opening-weekend gross confirmed Gyllenhaal's bankability. Lee's film, however, garnered the most acclaim of 2005, and offered him perhaps his riskiest, most rewarding role to date. Playing the closeted, romantically frustrated rancher Jack Twist, Gyllenhaal added heartbreaking shades of vulnerability to his usual frat-boy cockiness, and more than held his own opposite a memorably gruff, taciturn
Heath Ledger. As praise was heaped out upon the film and its two male leads, Gyllenhaal found himself the recipient of a BAFTA award, a National Board of Review notice, and an Oscar nomination for Best Supporting Actor.
Gyllenhaal would next appear in
David Fincher's
Zodiac, a 2007 film about the decades-long investigation into the Zodiac killer, who terrorized San Francisco in the 1970s. The actor was well received and the dark, proceedural film was a smash with critics.