Jake Gyllenhaal's Movies That Redefined Hollywood!

Jake Gyllenhaal led October Sky as Homer Hickam. The future star came into the gig after picking up early roles in City Slickers (1991), Josh and S.A.M. (1993), and Homegrown (1998).

October Sky

Jack Twist is one of two protagonists in Annie Proulx's novella Brokeback Mountain, as well as the 2005 film adaptation. He is a young cowboy from Wyoming who falls in love with fellow ranch hand Ennis Del Mar while herding sheep with him for a summer.

Brokebrake Mountain

American cartoonist and writer Robert Graysmith is mostly known for his book titled Zodiac. In his book, Graysmith provides his theory on the possible identities of the true Zodiac killer. Graysmith writes that Arthur Leigh Allen, Bob Starr, and Donald Andrews are possible suspects.

Zodiac

The dual role of Adam and Anthony undoubtedly ranks among Jake Gyllenhaal's best, not least because of the subtle differences between them. In fact, the distinctions between the two are so subtle that there is a strong argument for them being the same person all along.

Enemy

The role of Detective Loki was prime Gyllenhaal material, but the actor explained that he requested some changes to make the character even more unsettling. “The character was written one way, but I could see the essence of something else in it,” Gyllenhaal said of his first impressions of the script.

Prisoners