Best Jake Gyllenhaal Movies

The “Swifties” may not want to watch his movies for obvious reasons. But, let’s be honest, we hate to love him just as much as we love to hate him. He’s objectively not a great guy for a relationship, but he is an incredible actor and some of his best movies will make you think about them nonstop. He’s been working on his craft since he was a child, appearing in iconic movies for the last couple of decades.

With such a long career already under the American’s belt, there is plenty of choice when it comes to watching his work. Whether it is a dark thriller or a lighthearted romantic comedy, there is truly something for everyone within his portfolio of films. It is inevitable that the star has appeared in some pretty bad movies (who hasn’t?). But, there are many more films of his that are absolutely excellent, so here are our picks for the top 10 best Jake Gyllenhaal movies. We promise you’ll love them even though you don’t want to.

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10. October Sky

We mentioned that Jake Gyllenhaal has been acting since he was very young, so let’s kick things off with one of his finest films, released in 1999. October Sky is the true story of the son of a West Virginian who dreams of a life beyond the town. After seeing Sputnik 1 take flight, Homer (Jake Gyllenhaal) is instilled with a passion for rocket science. Despite his father’s disapproval, Homer sets out to build rockets with the help of his supportive teacher. This ultimately captures the attention of the town and eventually, a much more important organization.

You can watch October Sky on Amazon Prime Video.

9. Nocturnal Animals

In this psycho thriller, you will barely be able to hold back tears. As Amy Adams’ character reads a new novel written by her ex husband, she can’t help be feel the deep connection and see the implications of revenge. In the horrifying tale, a man’s wife and daughter are kidnapped after a strange encounter on a highway in a barren part of Texas. The husband teams up with a detective to track down the evil captors. Once they catch onto the two men who did this, they realize a much worse fate than they thought. As the plot progresses, you’ll forget that it’s all part of a novel. Gyllenhaal’s emotional performance is seriously impressive.

You can stream Nocturnal Animals on Netflix.

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8. Source Code

In this mind bending action sci-fi movie, Jake Gyllenhaal stars as a helicopter pilot who is reliving the final moments of a man who died in a commuter train explosion. This is all part of a secret government operation utilizing a mysterious new technology. By experiencing this man’s memories over and over, he must find the source of the explosion and the people responsible with just a few minutes. Source Code is a great action twist on the time loop movie formula that will have you on the edge of your seat. 

If you want to watch Source Code, you can stream it on Hulu or rent it on Prime Video.

7. Jarhead

 Best Jake Gyllenhaal Movies: Jarhead

Jarhead is a war movie set during Operation Desert Storm. It follows a marine who is training to be a sniper under the command of a menacing drill instructor. When the Gulf War begins, he and his spotter are shipped out for active duty and they must struggle to maintain their sanity in this thrilling and impactful film. It’s an important movie as it addresses the mentality and psychological health of a Marine in the United States. If you enjoy watching intense war films, you’ll definitely enjoy Gyllenhaal’s depiction.

Jarhead is available for free on Tubi.

6. Enemy

For one reason or another, the best Jake Gyllenhaal movies often find him in a mind-bending, psychologically thrilling plot. One of these is Enemy from acclaimed Canadian director, Denis Villeneuve. When a college professor with a boring life sees an actor on TV who is physically identical to him, he seeks out his doppelganger. With both roles played by Gyllenhaal, the coming together of these two individuals on the screen will keep you guessing right to the end. 

Enemy is available with Hulu subscriptions.

5. End of Watch

 Best Jake Gyllenhaal Movies: End Of Watch

End of Watch features two Los Angeles police officers documenting their daily patrols around some of the most dangerous areas of the city. Despite bending the rules here and there, the two are unquestionably dedicated to upholding the law, no matter the cost. This eventually leads them to cross the Mexican cartel, resulting in a dangerous series of events for the partners. Told through an interesting found footage medium, this police movie is packed with crime, action and emotion. 

You can rent End of Watch on Prime Video or watch with Apple TV.

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4. Donnie Darko

We have a couple of mind bending movies on this list already and here is yet another one. One of Jake Gyllenhaal’s earlier roles and one that went on to become a cult classic, Donnie Darko is a very interesting film. When a teenager named Donnie Darko begins sleepwalking, he sees a terrifying humanoid rabbit who tells him that the world will end in 28 days. After he awakens and gets home, he discovers that a jet engine has fallen out of the sky and crashed into his bedroom. Piecing together this parallel universe mystery has kept people captivated for years and is worth attempting to untangle for yourself. 

This movie is available to stream at home on Peacock.

3. Zodiac

Set during the late 60s and early 70s, this movie is based on the real life case of the zodiac killer. After several murders take place in San Francisco, cryptic coded messages are sent to the police department and journalists. This film explores obsession after several people involved are compelled to solve the case and get stuck on it for years. This includes a cartoonist named Robert Graysmith (Jake Gyllenhaal) who believes his unique puzzle solving abilities can help to find the killer.  Thrilling, epic and entertaining, David Fincher’s Zodiac is a must see Jake Gyllenhaal movie.

You can stream it now on Hulu or rent it on Prime Video.

2. Brokeback Mountain

Brokeback Mountain follows a cowboy (Jake Gyllenhaal) and a ranch hand (Heath Ledger) who are hired by a rancher to herd sheep in a remote mountainside location. After spending time isolated together, they eventually drunkenly act on their repressed feelings for each other. Despite their mutual attraction, the two men get married to women and we see their troubled relationship develop over the course of 20 years. Brokeback Mountain is a truly beautiful and tragic film, with great performances by both Jake Gyllenhaal and the late, great Heath Ledger. 

Check it out now on Hulu.

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1. Nightcrawler

If not the greatest Jake Gyllenhaal performance, this next role is certainly his creepiest one. Nightcrawler follows a man named Louis Bloom who is scavenging and stealing to get by. In a new money making scheme, he takes a camcorder and a police scanner to film crime scenes and sell the footage to news outlets. Discovering that he can garner more interest for footage of grisly and gruesome crimes, Louis goes further and further to get the perfect shot. 

If you’re not scared away, you can stream Nightcrawler on Hulu.

Whether you didn’t think you would like these movies because of Taylor Swift or because they’re all quite dark, we can guarantee that they will capture you in an undeniable way. His acting is emotional and raw, which might make us forget about knowing him “all too well.” If there is one thing you cannot deny, it’s the depth across his portfolio, so we recommend you give our 10 best Jake Gyllenhaal movies a try.