Jake Gyllenhaal Movies: 12 Greatest Films from ‘October Sky’ to ‘Brokeback Mountain’ to ‘Nightcrawler’ to ‘Stronger’

With this week’s release of the film “Stronger,” Jake Gyllenhaal might be back in the Oscar race for the first time in over a decade. This inspirational story is based on the real events surrounding the 2013 Boston marathon bombing. Gyllenhaal plays Jeff Bauman, based on his book of the same name. He is an ordinary man in Boston who became a symbol of hope after losing both legs in the tragedy.

Let’s take a look back at the impressive movie career of Gyllenhaal. Our photo gallery (view above) of his 12 greatest films features him starting in his teens with “October Sky” through his Academy Award nomination in “Brokeback Mountain” to the great reviews of the surreal thriller “Nocturnal Animals.”

Gyllenhaal began his career as a child actor alongside his sister Maggie Gyllenhaal. Born into the entertainment business, his father Stephen is a director and mother Naomi is a screenwriter. The first role in his career was in the 1991 comedy “City Slickers” playing Billy Crystal‘s son.

Our photo gallery doesn’t include that movie but does include some of the biggest and best films in his career. His breakthrough role was in the 1999 movie “October Sky.” He plays Homer, a young man in a small West Virginia town in 1957 who is expected to follow his father’s path of being a coal miner, but instead, inspired by the launch of Russian satellite Sputnik 1, Homer decides that he wants to be a rocket engineer himself. Aided by several other classmates, Homer considers himself a “rocket boy” (of which the film’s title “October Sky” is an anagram) and manages several successful rocket launches before the group is falsely accused of starting a forest fire.

In what is unquestionably Gyllenhaal’s most famous film role, he plays Jack Twist, who is hired to wrangle sheep on Wyoming’s “Brokeback Mountain “in 1963. Jack is sexually drawn to colleague Ennis del Mar (Heath Ledger), at whom Jack finally makes a pass, which leads to a long-term sexual and emotional relationship, even though both men eventually marry women. The sensitive performances delivered by both men garnered widespread acclaim, leading to Gyllenhaal’s first nomination for an Oscar, Golden Globe and Screen Actors Guild Award for Best Supporting Actor.

In one of Gyllenhaal’s darkest but most acclaimed roles in “Nightcrawler,” he portrays Louis Bloom, a petty thief who comes upon a grisly accident and sees freelance journalists swarming around the violent aftermath. After learning that stringers, as they are called, earn considerable money selling their footage to local TV news shows, Lou obtains a camcorder and begins selling his footage to an L.A. local station, whose news producer Nina Romina (Rene Russo) is very much of the “if it bleeds, it leads” school.

Tour our photo gallery above and see which Gyllenhaal films we selected. Did your favorite make the cut?

Be sure to make your Oscar nomination predictions so that Hollywood studio executives and top name stars can see how their films are faring in our Academy Awards odds. Don’t be afraid to jump in now since you can keep changing your predictions until just before nominees are announced on January 23. And join in the fierce debate over the 2018 Oscars taking place right now with Hollywood insiders in our film forums. Read more Gold Derby entertainment news.

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