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Put on another layer because later Gyllenhaal recounts his time meeting Obama and manages to bring it back to The Question.
A member of the Gyllenhaal family and the son of director Stephen Gyllenhaal and screenwriter Naomi Foner, Gyllenhaal began acting as a child with a screen debut in City Slickers (1991), followed by roles in A Dangerous Woman (1993) and Homegrown (1998).
Gyllenhaal's first lead role was in October Sky, Joe Johnston's 1999 adaptation of the Homer Hickam autobiography Rocket Boys, in which he portrayed a young man from West Virginia striving to win a science scholarship to avoid becoming a coal miner.
Gyllenhaal appeared in the 1993 film A Dangerous Woman (along with sister Maggie); in "Bop Gun", a 1994 episode of Homicide: Life on the Street; and in the 1998 comedy Homegrown.As the Hastings' ordinary, civilized lives are disastrously, violently sent off course, Susan is plunged back into the past, forced to confront the darkness that inhabits her, and driven to name the fear that gnaws at her future and will change her life. At the time, Gyllenhaal was nine years her senior—a minor scandal—but the relationship only lasted three months. In 2005, Gyllenhaal portrayed Anthony "Swoff" Swofford in Jarhead, Gwyneth Paltrow's love interest in Proof, and Jack Twist in Ang Lee's Brokeback Mountain.
For his performance in Brokeback Mountain, he 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.tall rabbit named Frank who tells him that the world is coming to an end.Gyllenhaal's performance was well received by critics; Gary Mairs of Culture Vulture wrote that "Gyllenhaal manages the difficult trick of seeming both blandly normal and profoundly disturbed, often within the same scene." After the critical success of Donnie Darko, Gyllenhaal's next role was as Pilot Kelston in 2002's Highway alongside Jared Leto.Writer Tim Jonze for the For someone so intensely private, wasn’t it playing with fire a little to start dating [Taylor Swift]? “I think when you’re in a relationship, you are constantly scrutinised, your friends are scrutinised, but ...” He trails off and stares at me, ramping up the intensity of his eyes like he’s done in so many roles.