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).
His breakthrough performance was as Homer Hickam in October Sky (1999) and he garnered an Independent Spirit Award nomination for Best Male Lead for playing the title character in the indie cult hit Donnie Darko (2001), in which he played a psychologically troubled teenager alongside his older sister, Maggie Gyllenhaal.
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It’s been a busy travel weekend for most Americans – and especially for Taylor Swift and Jake Gyllenhaal.
He subsequently appeared in another indie film, The Good Girl (2002) and the climate fiction-disaster film The Day After Tomorrow (2004), portraying a student caught in a cataclysmic climate event.
If we take a trip back down memory lane to when the beautiful beautiful duo appeared at the Academy Awards in 2010 together, it's as if the writing was on the wall for these stylish two.
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.
His performance was described by one critic as "silly, cliched and straight to video".
Two days after enjoying maple lattes together in Brooklyn, N.
Y., on Thanksgiving, Swift and Gyllenhaal popped up in the singer’s hometown of Nashville.