Top 5 Jake Gyllenhaal Movies


Jake Gyllenhaal remains in the running as one of the best American actors yet to win an Oscar (we’re looking at you, Leo!), as he has starred in a number of critically-acclaimed, challenging, and BOLD films! Take a look at our Top 5 Jake Gyllenhaal Movies list to see some of his most important films to date!

1) Nightcrawler

Nightcrawler Jake Gyllenhaal
  • When Louis Bloom, a driven man desperate for work, muscles into the world of L.A. crime journalism, he blurs the line between observer and participant to become the star of his own story. Aiding him in his effort is Nina, a TV-news veteran
  • Nominated for an Oscar for Best Original Screenplay and Jake Gyllenhaal was nominated for a Best Actor Golden Globe
  • Jake Gyllenhaal did most of his own driving scenes, including the climatic car chase at the end
  • The billboard for eyeglasses that Lou passes is reminiscent of the eyes of Dr. T.J. Eckleburg in The Great Gatsby; both stories address the idea of the American Dream and its flaws
  • Jake Gyllenhaal lost 20 pounds for his role. This was Gyllenhaal’s own idea, as he visualized Lou as a hungry coyote

2) Brokeback Mountain

Brokeback Mountain - Jake Gyllenhaal and Heath Ledger
  • The story of a forbidden and secretive relationship between two cowboys and their lives over the years
  • Nominated for eight Academy Awards, winning three (including Best Director and Best Adapted Screenplay)
  • During its first weekend of release (playing in only five theaters across the US), it set a record for highest per-screen gross of any non-animated film in history
  • The poster for the film was deliberately styled to resemble another romantic epic, Titanic
  • According to reports, Heath Ledger nearly broke co-star Jake Gyllenhaal’s nose while filming a kissing scene

3) Donnie Darko

Donnie Darko - Jake Gyllenhaal
  • A troubled teenager is plagued by visions of a large bunny rabbit that manipulates him to commit a series of crimes, after narrowly escaping a bizarre accident
  • The scene where Donnie corrects Gretchen was improvised because the actress could not say the name Prof. Kenneth Monnitoff correctly
  • During conversations about sex with his therapist, the script had Donnie’s fantasies about Alyssa Milano. This had to be changed to Christina Applegate for legal reasons
  • Currently ranked #199 on’s Top 250 Movies
  • Seth Rogan’s feature film debut

4) October Sky

October Sky Jake Gyllenhaal
  • The true story of Homer Hickam, a coal miner's son who was inspired by the first Sputnik launch to take up rocketry against his father's wishes
  • The author wished the movie to be called "Rocket Boys," like the book it's based on, but the studio believed that title would not sell well. The compromise title "October Sky" works on two levels: it's the month when the hero is first inspired by Sputnik, and it is an anagram of "Rocket Boys"
  • This film was released in the United States on February 19, 1999, which was also the 56th birthday of the real-life Homer H. Hickam Jr
  • The engineer driving the steam locomotive in the rail-harvesting scene was played by renowned railroad photographer O. Winston Link
  • Two of the real-life rocket boys, Sherman Siers and Jimmie O'Dell Carroll were combined into one character named Sherman O'Dell

5) Jarhead

Jarhead Jake Gyllenhaal
  • Based on former Marine Anthony Swofford's best-selling 2003 book about his pre-Desert Storm experiences in Saudi Arabia and about his experiences fighting in Kuwait
  • Filming lasted five months - which is the same length of time that the soldiers in the film spent in the desert
  • In the movie, the soldiers watch Apocalypse Now, which was edited by Jarhead editor Walter Murch
  • The burning oil wells were all computer generated. The oil that appears on the soldiers' faces was a concoction made from molasses
  • The "f" word and its variants are used 278 times in this film (38 times with the prefix "mother")

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