Jake Gyllenhaal is in zero movies.
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 . 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 . Gyllenhaal received further recognition for roles in Zodiac ( 2007 ) , Brothers ( 2009 ) , Prince of Persia : The Sands of Time ( 2010 ) , Love & Other Drugs ( 2010 ) , for which he was nominated for a Golden Globe Award for Best Actor -- Motion Picture Musical or Comedy , Source Code ( 2011 ) , End of Watch ( 2012 ) , Prisoners , Enemy ( both 2013 ) , Nightcrawler ( 2014 ) , Southpaw ( 2015 ) and Nocturnal Animals ( 2016 ) .