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 spend the next several years enjoying his status as a leading man, appearing in projects like Zodiac, Brothers, Love and Other Drugs, and Source Code.