All of the Jake Gyllenhaal movies showcase his gradual rise from intriguing young talent to one of the most reliable actors in Hollywood. He’s a performer who makes any movie he is a part of instantly more appealing. Jake Gyllenhaal’s filmography jumps between big-budget entertainment to small dramas, his parts from leading roles to supporting players. One thing that’s almost universally agreed — he always gives a stellar performance. That reliability as a character actor makes him a continued favorite among audiences, who seem to enjoy his smaller projects as much as his blockbusters.
Part of what makes has made Gyllenhaal’s filmography so impressive is how the actor seems willing to try new things, seeks out interesting filmmakers, and challenges himself with his performances. He has taken supporting roles in award-winning movies, led massive blockbusters, played the dashing hero, and intimidated as the dark villain. The best Jake Gyllenhaal movies not only highlight his talents but also the quality of projects he chooses throughout his career.
15 Everest (2015)
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Available to rent on Apple TV
Though he is often seen as a Hollywood leading man, Gyllenhaal is often just as likely to appear in a supporting role within a larger ensemble. Such is the case with Everest which tells the true story of a fateful expedition to climb Mount Everest which resulted in the deaths of several climbers. Gyllenhaal plays Scott Fischer, one of the more experienced climbers in the group. The movie is an intense and powerful survival story featuring a stellar cast, including Josh Brolin and Jason Clarke. It shows the determination of these climbers to achieve something extraordinary but the perils that befall them.
14 Okja (2017)
Whether in lead roles or smaller supporting parts, Gyllenhaal seems drawn to working with talented filmmakers. He teamed with Oscar-winner Bong Joon-ho for the adventure Okja. It follows a young girl living in a small Korean village who sets out to save her best friend, a giant pig, who has been kidnapped. Gyllenhaal has a small but memorable role as a hypocritical animal rights activist. It is an entertainingly over-the-top performance within this wild story. Though it contains his distinct sense of humor and genre-blending, it is also very different from Bong Joon-ho’s other movies with a more magical feel.
13 Brothers (2009)
Gyllenhaal joins other acclaimed actors Tobey Maguire and Natalie Portman in the intense drama Brothers. Gyllenhaal plays the wayward brother of Maguire’s soldier serving overseas. After Maguire is presumed dead, Gyllenhaal begins helping out his sister-in-law (Portman) and developing a strong bond. But tensions grow when his brother unexpectedly returns. The cast really makes the most of the intimate and powerful story with Maguire stepping away from his Spider-Man role to deliver a truly intense performance. It is filled with moments of heartbreaking sadness and unsettling confrontation that make for a compelling thriller.
12 Nocturnal Animals (2016)
Nocturnal Animals is a great example of how Gyllenhaal seems drawn to smaller films from interesting filmmakers and featuring a great cast. The movie stars Amy Adams as a woman reading the new novel from her ex-husband (Gyllenhaal) as she begins to see parallels between their relationship and the violent story. The movie does not easily fit into any one category. It switches between the existential crisis of Adams’ character and the unsettling dramatization of the novel she’s reading. The moody and somber tone is effective throughout as are the performances, especially Michael Shannon’s Oscar-nominated role as a cop willing to work outside the law.
11 Source Code (2011)
Whenever Gyllenhaal does take on a more mainstream genre movie, you can bet there is something interesting about the story that provides the actor with a challenge. Source Code fits that description as the sci-fi thriller stars Gyllenhaal as a soldier who is sent back in time to relive a train bombing again and again so he can learn the identity of the bomber. The high-concept story provides an extremely intriguing jumping-off point for the film that keeps unraveling new details about the mystery. Gyllenhaal is great as the confused hero thrown into an impossible situation. The movie was a crowd-pleasing hit, mixing the action and sci-fi genres effectively. And Source Code‘s ambiguous ending still has people talking about it.
10 Southpaw (2015)
Gyllenhaal has always been a deeply committed actor and that certainly shows in this intense sports drama. Southpaw is inspired by Eminem despite being a sports movie — Gyllenhaal plays a champion boxer who suffers a personal tragedy that sends him into a destructive downward spiral. He then sets himself on a path to regain his championship and win back his daughter. Gyllenhaal’s impressive transformation is only the start of what makes his performance so compelling. The movie itself is a fairly standard sports drama and redemption tale, but it features one of Gyllenhaal’s best performances which elevates the material.
9 End Of Watch (2012)
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Available to rent on Apple TV
Cop movies as a dime a dozen in Hollywood, but End of Watch found a unique and interesting take on the genre. The David Ayer film stars Gyllenhaal and Michael Peña as LAPD partners who inadvertently become the target of the cartel after making a shocking discovery. The movie uses the found-footage template, telling the story in a voyeuristic way. It feels like an authentic exploration of the life of police without painting a pretty picture as some Hollywood movies tend to do. Gyllenhaal and Pena are excellent, playing the fun aspects of the buddy duo while their bond is one that audiences genuinely care about.
8 Jarhead (2005)
One of the movies that really launched Gyllenhaal as a leading man was the Sam Mendes-directed war movie Jarhead. Gyllenhaal plays an aimless young man who joins the army and is shipped out for deployment during the Gulf War where he contends with boredom and isolation. The movie is a fascinating study of the modern soldier in a unique type of war movie without big battles or action sequences, but rather focusing on the mindset of these soldiers. Gyllenhaal brings a lot to the role with humor, intensity, and heartbreak. It also features strong supporting roles from Peter Sarsgaard and Jamie Foxx among others.
7 Spider-Man: Far From Home (2019)
Gyllenhaal may have circled superhero movies earlier in his career, but it was still a surprise to see the critical darling joining the MCU. Spider-Man: Far From Home finds Peter Parker (Tom Holland) taking a break from his superhero life while on a school trip across Europe. However, he is pulled back in by the emergence of a new threat, as well as a new “hero” named Mysterio (Gyllenhaal). The sequel continues to prove Spider-Man is having a lot of fun as part of the MCU. The movie wisely maintains the high school feel along with all the awkwardness and embraces its comedic side. Gyllenhaal is clearly having a ball with his role as Mysterio and his villainous twist. The movie was a bigger hit than its predecessor and cemented Spider-Man one of the MCU’s biggest solo franchise.
6 October Sky (1999)
Gyllenhaal scored his first major leading role as a relatively young man in the period drama October Sky. Based on true events, Gyllenhaal stars as a young man living in a coal mining town in the 1950s. After being inspired by the first Russian satellite launch, he discovers his love of rocketry. Gyllenhaal immediately proves his potential as a leading man. He is charming, inspiring, funny, and powerful as a young man whose dreams seem beyond the realities of his life. The film itself is a moving tale likely to bring more than a few tears to viewers’ eyes. It also marks an impressive breakout role for Gyllenhaal.
5 Zodiac (2007)
David Fincher is responsible for some incredible and popular films over his career, but Zodiac remains an underrated true-crime masterpiece in his filmography. The film takes a look at the decades-long investigation into the Zodiac Killer and the various individuals involved in the case. Gyllenhaal plays Robert Graysmith, a real-life cartoonist who becomes obsessed with the murders. Fincher’s dark and creepy tone works perfectly for the movie, which takes a look at the real investigation with fascinating detail. The cast is wonderful and there is a strange but welcome sense of humor throughout. It is unsettling yet engrossing. While the movie didn’t make much of an impact upon its release, its reputation has only grown with it recently being named one of THR‘s Best Movies of the 21st Century (So Far).
4 Nightcrawler (2014)
While he was once seen as the next big movie star in Hollywood, Gyllenhaal has taken a much more interesting route filled with challenging and complex roles. In Nightcrawler, he stars as Lou Bloom, a determined but unhinged professional who tries to break into the seedy business of freelance crime journalism. Gyllenhaal is transformative in perhaps his finest performance to date. He is scary and grotesque despite the fact that he usually has a smile on his face. The movie is a fascinating and perverse take on the American dream and what some are willing to do to achieve it. Many consider Lou Bloom to be Gyllenhaal’s best performance to date.
3 Prisoners (2013)
Denis Villeneuve has become one of the most exciting filmmakers in Hollywood, and his first English-language film immediately showed him to be a visionary director. Prisoners is a dark thriller about two families whose daughters go missing. One of the fathers (Hugh Jackman) goes to extreme lengths to bring his child home while a determined detective (Gyllenhaal) investigates. A solid mystery is hard for audiences to resist, especially with this amount of talent in front of and behind the camera. The performances are all intensely effective, and Villeneuve casts an ominous tone over the entire story leading up to Prisoner‘s powerful ending.
2 Donnie Darko (2001)
Gyllenhaal came to many people’s attention with his role as the titular character in Donnie Darko. The mind-bending film follows a strange young man who, after surviving a near-fatal freak accident, begins having visions of a man dressed in a terrifying bunny costume who tells him to commit various crimes. This is another film that is very hard to categorize, but there’s no denying that it is a compelling and haunting film that takes the audience down a strange rabbit hole. With fans still debating Donnie Darko’s ending and the meaning of the overall movie, it has gained a huge cult following.
1 Brokeback Mountain (2005)
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Gyllenhaal began to move outside his boyish roles and into more adult roles with the Best Picture nominee Brokeback Mountain. The Ang Lee film begins in the 1960s and follows two sheepherders (Gyllenhaal and Heath Ledger) who begin a passionate affair while working together one summer. The story follows the two men throughout the years as they maintain their relationship while hiding it from their families. The film is as beautiful to look at as the story is to experience. Ledger and Gyllenhaal are heartbreaking as two men who bottle up their true feelings. It remains one of the most important cinematic love stories of all time. Both Gyllenhaal and Ledger were nominated for their performances while Ang Lee won for Best Director.