Jake Gyllenhaal is in zero movies.
Brokeback Mountain is a 2005 American neo-western romantic drama film directed by Ang Lee and produced by Diana Ossana and James Schamus . Jake Gyllenhaal . 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 . October Sky is a 1999 American biographical film directed by Joe Johnston , starring Jake Gyllenhaal , Chris Cooper , Chris Owen , and Laura Dern . Southpaw is a 2015 American sports drama film directed by Antoine Fuqua , written by Kurt Sutter and starring Jake Gyllenhaal , Forest Whitaker and Rachel McAdams .