What are the best Jake Gyllenhaal movies? It’s impossible to think about Hollywood without then thinking about Jake Gyllenhaal, as his vast, genre-spanning acting CV makes him almost interchangeable with the modern film industry as a whole.
From drama movies to action movies, and even the MCU — Jake Gyllenhaal has done everything. But which of his iconic roles come out of top, and what can be considered his best movie? Well, here’s what I consider to be the best Jake Gyllenhaal movies of all the time. I wish I knew how to quit you, Jake.
The best Jake Gyllenhaal movies of all time
- Spider-Man: Far From Home
- Prisoners
- Zodiac
- Nightcrawler
- Brokeback Mountain
- Donnie Darko
Spider-Man: Far From Home (2019)
Throughout his career, Gyllenhaal has portrayed movie villains numerous times, with several of them deserving a place on this list. But his turn as Spider-Man villain Mysterio sticks out because of how calculated Gyllenhaal made the character. Mysterio was so charming at first, and played so well by Gyllenhaal; his being the bad guy felt like a genuine betrayal — and given Mysterio was still causing chaos from beyond the grave, it’s impossible to dispute the character’s impact.
Prisoners (2013)
Starring opposite fellow Marvel movie star Hugh Jackman, Gyllenhaal is posited as the calming influence in this film. As Detective Loki, he is tasked with bringing a disturbed child kidnapper to justice, and in an understated yet powerful performance, acts as the foil to the more traumatised, explosive parent (Jackman) of one of the kidnapper’s victims who will stop at nothing to get justice for his child.
Zodiac (2007)
Gyllenhaal perfectly toes the line between vulnerable and disturbing in this David Fincher thriller movie. Based on the real-life hunt for the Zodiac Killer, Gyllenhaal plays Robert Graysmith, a newspaper cartoonist who becomes increasingly obsessed with the case as the killer continues to send taunting notes to the paper.
Nightcrawler (2014)
Lou Bloom is considered one of the best performances of Gyllenhaal’s career, and for good reason. After stumbling upon a gruesome murder, Bloom becomes seduced by the dark world of freelance crime journalism — which involves capturing and distributing footage and images of grisly crime scenes. As he chases this grim manifestation of the American Dream, the character becomes more and more twisted, with Gyllenhaal never failing to chill us straight to the bone.
Brokeback Mountain (2005)
A gentle, meditative twist on the Western genre, Gyllenhaal and Health Ledger star as Jack Twist and Ennis del Mar, respectively. Over the span of two decade, the two star-crossed lovers embark on a romance that makes them question everything they thought they knew about society, love, and, most importantly, themselves. As Jack Twist, Gyllenhaal gives what is perhaps his most emotionally raw performance yet: handling his character’s story with the dignity, respect, and sensitivity it deserves. The result? A romance movie that is both devastatingly beautiful and a much-deserved Academy Award nomination for Gyllenhaal.
Donnie Darko (2001)
At just 20 years old, Gyllenhaal stunned moviegoers and critics alike with his deeply impactful performance in Donnie Darko. In this mind-bending science fiction movie, Gyllenhaal stars as the titular character — a troubled young man who, after a freak accident, begins to be taunted by visions of a humanoid rabbit who, in turn, encourages Darko to commit a chain of increasingly-disturbing crimes. Proving himself to be capable beyond his years, Gyllenhaal delivered a performance so outstanding, the film gained cult-classic status, and continues to boggle people’s minds to this day. Without Donnie Darko, would we even have Jake Gyllenhaal?
To see more actors’ humble beginnings and career-defining roles, check out our guides to the best Tom Hanks movies, best Chris Evans movies, and best Tom Cruise movies. Or keep your eyes on the prize and check out our guide to some of the best new movies coming your way this year.