He may still be hunting for his first Oscar, but Jake Gyllenhaal has already more than proven that he’s one of modern Hollywood’s greatest leading men. What’s made his career so fascinating is that he’s mostly shied away from the biggest projects that were offered to him, barring the occasional video game adaptation.
Gyllenhaal’s best performances speak to the wide array of roles he’s willing to take on and how different his approach seems to be from project to project. He’s not the kind of actor who repeats himself, and that makes every one of his performances a revelation. These are the best Jake Gyllenhaal movies over the span of his long and winding career.
For more great movies, check out our lists of the best movies streaming on Netflix, the best movies available on Hulu, and the best titles available on Disney+.
10. Enemy (2013)
91m
Genre
Thriller, Mystery
Stars
Jake Gyllenhaal, Mélanie Laurent, Sarah Gadon
Directed by
Denis Villeneuve
Both of Gyllenhaal’s collaborations with Denis Villeneuve are excellent, but his work in Enemy is what makes the movie possible. Gyllenhaal stars in two roles. He plays a college professor and the actor who could be his twin. The two men’s lives begin to meld and twist until the boundaries surrounding their own identities are completely blurred. Few actors could pull off this kind of performance while making both characters feel and seem distinct, and it’s because Gyllenhaal is so smart about how each of these men operate in the world that the movie is believable.
9. Okja (2017)
122m
Genre
Adventure, Drama, Science Fiction, Fantasy
Stars
Ahn Seo-hyun, Tilda Swinton, Paul Dano
Directed by
Bong Joon-ho
Jake Gyllenhaal is capable of turning in sensitive, smart, subtle performances when he wants to. What’s especially great about him is that he also knows when to go huge. In Okja, Gyllenhaal has a supporting role as a doctor working for a major agricultural company, and he just aims for the rafters. It’s one of the biggest performances of his entire career, but it works because it’s never what you expect it to be. Gyllenhaal made a fairly sizable gamble when he decided to go big, and it paid off. In that way, it has a lot in common with his performance in Ambulance.
8. Donnie Darko (2001)
114m
Genre
Fantasy, Drama, Mystery
Stars
Jake Gyllenhaal, Jena Malone, James Duval
Directed by
Richard Kelly
Ths was the performance that proved that Gyllenhaal had a long career ahead of him. Donnie Darko continues to hold a strange cult power even decades after its initial release. Gyllenhaal’s central performance is key to what makes this movie shine, as we are fixed to Donnie’s perspective as he wonders how much of what he’s seeing is actually real. You could knock Donnie Darko as overly stylized or strange, but its power comes in part from its willingness to explore the darkest corners of its protagonist’s mind.
7. The Sisters Brothers (2018)
122m
Genre
Comedy, Drama, Western
Stars
John C. Reilly, Joaquin Phoenix, Jake Gyllenhaal
Directed by
Jacques Audiard
In addition to delivering outlandishly large performances, Gyllenhaal has proven himself to be an excellent comedian when he wants to be. In The Sisters Brothers, he plays a comically inept private detective who ultimately finds himself tangled up with the titular brothers. Even as Gyllenhaal’s character is genuinely amusing, it never feels like Gyllenhaal is just going for a cheap laugh. The Sisters Brothers is a generally underrated film, and that’s especially true of Gyllenhaal’s excellent supporting performance.
6. Brokeback Mountain (2005)
134m
Genre
Drama, Romance
Stars
Heath Ledger, Jake Gyllenhaal, Michelle Williams
Directed by
Ang Lee
Heath Ledger often gets the lion’s share of the attention for his performance in Brokeback Mountain, and deservedly so, but none of what Ledger does would be possible without Gyllenhaal at his side. This movie is a true team effort, and Ledger’s quiet, internal performance is perfectly matched by the more bombastic but never showy work that Gyllenhaal does. There’s not a bad performance to be found in Brokeback Mountain, actually, which is part of what made it such an overwhelming critical favorite upon its release and an enduring favorite today.
5. Stronger (2017)
119m
Genre
Drama
Stars
Jake Gyllenhaal, Tatiana Maslany, Miranda Richardson
Directed by
David Gordon Green
One of the more underrated movies in Gyllenhaal’s filmography, Stronger tells the story of Jeff Bauman, a man who lost both his legs in the Boston Marathon bombing. While the movie could have been a fairly conventional story of triumph over adversity, it instead becomes a thoughtful meditation on the way we try to force that narrative onto anyone who survives a tragedy. Gyllenhaal and Tatiana Maslany are both excellent here, especially in a standout sequence where Jeff is brought out ahead of a Bruins hockey game.
4. Zodiac (2007)
157m
Genre
Crime, Drama, Mystery, Thriller
Stars
Jake Gyllenhaal, Mark Ruffalo, Robert Downey Jr.
Directed by
David Fincher
David Fincher’s ode to obsession and one of his very best films, Zodiac was also an early indication that Gyllenhaal was going to be around for a while. A newspaper cartoonist who finds himself inexorably drawn toward the case of the Zodiac killer, Gyllenhaal’s character slowly lets the case consume his entire life, even as it fades from the headlines. Zodiac is about a real reckoning with evil and about the way that amateur sleuths can ruin their own lives in pursuit of truths that prove to be consistently illusory.
3. Source Code (2011)
94m
Genre
Thriller, Science Fiction, Mystery
Stars
Jake Gyllenhaal, Michelle Monaghan, Vera Farmiga
Directed by
Duncan Jones
Over his years as an actor, Gyllenhaal hasn’t starred in that many great pure action movies, but Source Code is something of an exception. Telling the story of a man who has to relive the same eight minutes over and over until he prevents a train from blowing up, Source Code is ultimately a love story, but one with plenty of twists and turns along the way. Gyllenhaal manages to ground Source Code‘s premise and make every moment on screen feel urgent and tactile.
2. Wildlife (2018)
105m
Genre
Drama
Stars
Jake Gyllenhaal, Carey Mulligan, Ed Oxenbould
Directed by
Paul Dano
Paul Dano’s directorial debut was one of the best movies of 2018, and Gyllenhaal’s supporting turn as a frustrated father who leaves his family is one of many reasons why. Wildlife is told from the perspective of a young boy as his parents’ marriage unravels. Carey Mulligan gets plenty of room to shine here, and Gyllenhaal essentially disappears for most of the runtime. When he does return, though, his portrayal of a wounded man who finds himself incapable of caring for his young family reminds us why an actor like Gyllenhaal was so crucial to the movie as a whole.
1. Nightcrawler (2014)
118m
Genre
Crime, Drama, Thriller
Stars
Jake Gyllenhaal, Rene Russo, Riz Ahmed
Directed by
Dan Gilroy
Often regarded as featuring Gyllenhaal’s best performance, Nightcrawler saw the actor lose a substantial amount of weight in order to play Louis Bloom, a freelance videographer willing to violate all sorts of ethical boundaries to get the violent, gruesome footage that local news thrives on. Gyllenhaal’s performance here is deeply upsetting and unnerving, but the systems around Louis that allow him to thrive are just as disturbing and help us to understand why Louis believes that he needs to cross so many lines to get ahead.
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