Digital Spy takes a look back at Gyllenhaal's five finest movies below.
Donnie Darko (2001)
Plagued by visions of a giant bunny rabbit predicting the end of the world, high-schooler Donnie Darko dodges death when a plane engine drops through his bedroom ceiling, falls in love with classmate Gretchen Ross (Jena Malone) and travels back in time to save the world. Gyllenhaal has the moody teen schtick down pat and delivers writer/director Richard Kelly's snarky one-liners with dry aplomb.
Brokeback Mountain (2005)
Any doubts that lingered over Gyllenhaal as a 'serious actor' soon evaporated with the release of Ang Lee's drama about forbidden love on a Wyoming cowboy ranch. Gyllenhaal's Jack Twist embarked on a lengthy love affair with Ennis Del Mar, a role superbly inhabited by the late Heath Ledger. Brokeback proved to be a hugh commercial and critical success, earning Gyllenhaal a much-deserved 'Best Supporting Actor' Oscar nomination.
David Fincher's police procedural - based on the true story of a serial killer who terrorised San Francisco in the '70s - saw Gyllenhaal take on the role of Robert Graysmith, a newspaper cartoonist who becomes deeply involved in the case. Touching on the recurring Fincher theme of obsession, Zodiac proved to be a difficult experience for Gyllenhaal, who took issue with the director's need for multiple takes. There's method to Fincher's madness, however, and the underrated Zodiac gave Gyllenhaal an intense character to sink his teeth into.
Love and Other Drugs (2010)
Ed Zwick's film cast Gyllenhaal as a smooth-talking drugs rep who falls hard for Anne Hathaway's Maggie, a stage 1 Parkinson's disease patient. The movie drifts through the rollercoaster that is romance, giving Gyllenhaal the perfect opportunity to utilise his natural screen charisma and dramatic acting chops. There's an effortless chemistry between the leading duo, too, showing that Gyllenhaal can cut it as a romantic leading man as well as an intense brooder.
Source Code (2011)
Duncan Jones's wickedly inventive science fiction thriller saw a soldier forced to re-live the same moment over and over in a bid to stop a bomb detonating on a commuter train. Gyllenhaal's Colter Stevens repeatedly wakes up in the body of a school teacher who must stop the bomb, piece together his own past and deal with his growing affection for school teacher Christina (Michelle Monaghan). It's a multi-faceted role, and one that takes an actor of Gyllenhaal's talents to make convincing.
Disagree with our Jake Gyllenhaal top five? Should October Sky, The Good Girl or The Day After Tomorrow have made the list? Leave your comments below!