11 Best Jake Gyllenhaal Movies, Ranked

For most of the 2020s so far, Jake Gyllenhaal has leaned towards movies heavy on punching and explosions, like his injury-laden experience shooting the "Road House" remake or his super maximalist work anchoring "Ambulance." Before this decade, however, Gyllenhaal was most famous for headlining artsy features of all kinds. Sure, there were some mainstream critical duds Gyllenhaal regrets starring in, like "Prince of Persia: The Sands of Time" or "Bubble Boy." Mostly, though, Gyllenhaal was known as an actor who took chances on challenging roles. The kinds of characters other performers in his age range would avoid like the plague were just the sort that Jake Gyllenhaal readily embraced.

Over the course of this daring career, Jake Gyllenhaal has delivered several acclaimed performances in some unforgettable modern classics. Gyllenhaal's 11 best movies exemplify his greatest traits as a actor and the kind of button-pushing material he's unafraid to grapple with. Some of Gyllenhaal's best movies excel because of his work as a lead performer, while others flourish because of a smaller but no less critical role in a larger ensemble cast. Still others prosper because they uncover new sides of Gyllenhaal previously unseen on film. Today, Gyllenhaal is a fixture of streaming titles directed by Doug Liman or Antoine Fuqua that are forgotten as soon as they drop. These 11 outstanding movies, on the other hand, reflect the true depth and talent defining his greater filmography. 

"Brothers" is a grueling motion picture to sit through. Jim Sheridan's 2009 directorial effort chronicles Captain Sam Cahill (Tobey Maguire) being seemingly killed in Afghanistan, with his brother Tommy (Jake Gyllenhaal) and wife Grace (Natalie Portman) struggling to cope with this reality when Cahill suddenly shows up alive. After months as a prisoner of war, undergoing extreme torture that viewers witness, re-adjusting to civilian life is no easy task for Sam — especially since he suspects that Tommy slept with Grace while he was away. 

For all its weighty ideas, "Brothers" unquestionably can't avoid certain pitfalls of 2000s Iraq War cinema, including shallow depictions of Afghanistan civilians and derivative visual impulses in depicting torture. However, "Brothers" also flourishes first and foremost as an acting exercise thanks to the deeply committed performances of its main three actors. Maguire really excels in his harrowing, tortured role, but don't count out Gyllenhaal either in his supporting work as Tommy. His portrayal is riddled with specificity and nuance, especially in his scenes where he's interacting with Grace alone.

Is there sexual attraction there or simple platonic support? Gyllenhaal keeps you guessing just with the way he moves his eyes around. His handling of Tommy gradually realizing how psychologically damaged the resurfaced Sam is, meanwhile, utterly shatters your heart. The discernible and distinctive humanity Gyllenhaal imbues in Tommy reflects how "Brothers" stands above other 2000s "War on Terror" features.

One reason "The Sisters Brothers" ranks so highly in Jake Gyllenhaal's filmography is that it isn't his movie. The two titular cowboys, Eli (John C. Reilly) and Charlie Sisters (Joaquin Phoenix), are the protagonists, with writer-director Jacques Audiard (adapting Patrick deWitt's 2011 novel of the same name) chronicling the ceaseless external and internal misfortune that the duo encounter on their quest to assassinate one man. In the middle of all this is Gyllenhaal's private detective, John Morris, who tracks down the brothers' target, Hermann Warm (Riz Ahmed), only to strike a deal with a man he discovers is innocent.

Gyllenhaal portrays Morris as a man clinging to both scruples in a world gone mad and hopes that Warm's formula (which detects gold submerged in rivers) can lead him to a better life. In other words, he's an eye in a hurricane, a calmer, sensible contrast to the chaotic Old West world as well as the innately tortured disposition of those Sisters brothers. This role is quite perfect for Gyllenhaal, who proves mighty capable of inhabiting a dramatic role that doesn't require lots of overt tics or an extreme physical makeover. It's also utterly fascinating to see a modern leading man be just another member of the "Sisters Brothers" ensemble. The fact that Gyllenhaal meshes so well and doesn't constantly draw attention to himself is a quietly spectacular feat.

In the late 2010s and early 2020s, the time loop movie had a resurgence thanks to motion pictures like "Happy Death Day," "Palm Springs," and "The Endless." A few years before those films, however, director Duncan Jones tackled the concept with Jake Gyllenhaal in "Source Code." This April 2011 release saw Gyllenhaal portray Colter Stevens, a man who awakens on a train in a body that isn't his. It turns out he's been sent back in time to stop a terrorist attack on a train, with Stevens constantly re-living the same eight minutes over and over until he can find some critical clues.

"Source Code" has its messy qualities (including an ending that understandably raised some eyebrows) but it's also got a creative spirit that, like the best time loop movies, finds the excitement in constantly re-experiencing the same events ad nauseum. Gyllenhaal is also a fun fit for the lead role of Captain Colter Stevens since he's able to exude an everyman spirit that might not effectively come through in other brawny modern leading men like Chris Hemsworth. With Gyllenhaal, his vulnerability and uncertainty in his bizarre scenario feel tangible and real.

There's also vivid emotional urgency to his on-screen work that keeps viewers glued to the screen no matter how high-concept and convoluted the film gets. Happily, Gyllenhaal shines as the anchor of "Source Code," which functions just fine as a Saturday afternoon movie and a pleasant precursor to a wave of time loop features.

Jake Gyllenhaal's unexpected niche as a leading man, it turns out, is playing compelling investigator characters trying to solve crimes that uncover the darkest parts of humanity. Six years after starring in "Zodiac," Gyllenhaal returned to this domain to portray Detective Loki in "Prisoners." Here, he's searching for the missing daughters of Keller Dover (Hugh Jackman) and Franklin Birch (Terrence Howard). While Dover succumbs to his most brutal impulses in trying to recover his daughter, Loki goes the old-fashioned sleuth route in uncovering clues and the larger meaning behind seemingly inexplicable trinkets to unearth the missing kids.

While Jackman's very pronounced performance takes up a lot of the oxygen in "Prisoners," Gyllenhaal's quietly believable work can't be discounted. He proves a terrific, deeply trustworthy protagonist for audiences to follow into truly unnerving territory. This quality makes the most harrowing moments involving Loki, when he assaults a suspect, hit your soul like a ton of bricks.

Gyllenhaal's gifts as a performer are exemplified in the final scene, as Loki silently wanders around a crime scene and then, in the distance, hears the blowing of a whistle that belongs to Dover. This burst of physical acting is rich with details confined almost exclusively to Gyllenhaal's face. He doesn't need a monologue or didactic exposition to end "Prisoners" on an appropriately grueling and grim note. Once again, putting Gyllenhaal into the role of an investigator in a bleak crime thriller pays off divinely. 

David Gordon Green's "Stronger" got lost in the shuffle in 2017, partially because it came out after "Patriot's Day," another movie about the 2013 Boston Marathon bombing. Green immediately helming a trilogy of divisive "Halloween" features after "Stronger" certainly didn't help this stirring drama gain much pop culture momentum. Still, this saga of Jeff Bauman (Gyllenhaal) recovering from losing his legs in the Boston attack is a deeply moving affair. Part of what makes it work so well is John Pollono's screenplay. "Stronger" takes a more expansive look at Bauman's struggles, daring to paint him as a complicated person rather than a one-note uplifting caricature for able-bodied viewers.

"Stronger" restores nuance to Bauman, a mission Gyllenhaal compliments terrifically with his multi-layered performance. Bauman is capable of being a jerk, selfish, and deeply flawed, rather than the perfect angel strangers often reduce him to because of his injuries. There's a welcome level of naturalism to Gyllenhaal's portrayal that's devoid of exaggerated external flourishes, a happy departure from how many able-bodied performers portray disabled historical figures.

Whatever corner of Bauman's mutli-faceted personality "Stronger" is exploring, Gyllenhaal renders its on-screen with intimacy and emotional urgency. Gyllenhaal also has robust and tremendously lived-in chemistry with co-lead Tatiana Maslany, who plays Bauman's girlfriend Erin Hurley. "Stronger" may have tragically descended into pop culture obscurity but don't let that fate erase its virtues and Gyllenhaal's excellent work here.

"Enemy" offers a rich acting opportunity for somebody like Jake Gyllenhaal, who gets to play two men who look exactly like each other. One is a buttoned-up college professor, the other a more brash actor. They may look like they rolled off an alternate version of "Mickey17," but they couldn't be more starkly different in personalities. Getting to inhabit two wildly contrasting characters like this ensures that 2013's "Enemy" features one of Gyllenhaal's most inventive performances. He's so adept at making both protagonists feel like fleshed-out individuals in their own right that they work well as on-screen figures even when you're not being reminded of that whole unique "doppleganger" quirk.

Gyllenhaal's performance is the centerpiece of a trippy surrealist drama with no interest in fulfilling mainstream cinema conventions. The doppelganger narrative is just the tip of the movie's weird iceberg. Director Denis Villeneuve crafts a project that mirrors Gyllenhaal's conviction as an actor. Both the film as a whole and Gyllenhaal's acting are captivating, right up to that divisive final shot that led to some audience members declaring "Enemy" a work of genius and others throwing up their hands in confusion. 

Provoking such strong reactions demonstrates that "Enemy" did something right, especially when it came to realizing Gyllenhaal's deftness with playing off himself. If you want two brain-challenging Jake Gyllenhaal performances for the price of one, then seek out the unnerving and unorthodox world of "Enemy" pronto.

Only once in his lengthy career has Jake Gyllenhaal scored an Oscar nomination. That nod (in the best supporting actor category) came for, of course, "Brokeback Mountain," a film that really cemented Gyllenhaal as a major dramatic actor and not just a pretty boy fronting Roland Emmerich movies and cult classic genre features. Gyllenhaal plays Jack Twist, one-half of the film's central Western romantic couple, with Heath Ledger's Ennis Del Mar taking on the role of Twist's lover. There's a wild cockiness to Gyllenhaal's Jack that sharply contrasts to the moodier work conjured up by Ledger. In the hands of this leading man, Jack Twist has as much boundless enthusiasm as the desert landscape has grains of sand. 

Most importantly, Gyllenhaal's sequences with Ledger are transfixing thanks to the pair's dynamic chemistry. Gyllenhaal, like Ledger, peppers their interactions with a mixture of seemingly paradoxical emotions (hesitancy, lust, concern, etc.) that mingle together to form an inescapable sense of passion. There's a yearning for Ennis underneath Jack's exterior that Gyllenhaal rustles up effortlessly. Gyllenhaal even excels here in the tiniest details, like his authentic rapport interacting with livestock or the way he easily slips into a period-era setting. Love is a complicated concept that's not easy to comprehend or grapple with, especially for this movie's two leads. Jake Gyllenhaal recognized this reality and imbued Jack Twist with such an appropriately nuanced performance that the Academy Awards had to take notice.

It's understandable why Jake Gyllenhaal's work in "Wildlife" didn't get much in the way of praise when this 2018 feature opened. Much of the attention (rightfully so) went towards Carey Mulligan's lead performance as well as Paul Dano's assuredness behind the camera in his directorial debut. However, Gyllenhaal's work as absent firefighter father Jerry is still tremendously impactful. Gyllenhaal especially works well in depicting Jerry's tragic desire to inhabit a perfect "father knows best" archetype that doesn't really exist. He's a deeply vulnerable man who futilely yearns to become a portrait of pristine, invincible mid-20th-century masculinity. 

It's a remarkably aching turn from Gyllenhaal, who devastatingly captures a man desperate to achieve societal standards that are also strangling him and his family. Dano's innately understated approach to shooting "Wildlife," meanwhile, means that Gyllenhaal dials back the delightfully wacky maximalism defining his hysterical supporting turns in things like the 2019 children's special "John Mulaney and the Sack Lunch Bunch." 

Operating in a subdued mode doesn't lessen Gyllenhaal's talent. On the contrary, it's impressive he can alternate between his transfixing over-the-top "Okja" antics and communicating such muted anguish in the role of Jerry. Plus the way he's able to leave an impression even though Jerry's often fighting a wildfire off-screen is remarkable. A quiet portrait of domestic life gradually crumbling, "Wildlife" isn't just a tremendous directorial debut. It's also a vessel for one of Gyllenhaal's greatest and subtlest performances.

Richard Kelly's directorial debut, "Donnie Darko," is full of confusing moments that inevitably inspired divisive reactions from some viewers. However, all moviegoers who absorbed this arrestingly unique title tended to walk away with one key response: Jake Gyllenhaal excels in the titular lead role. Playing a troubled teenager plagued with visions of surreal things like a gigantic human-sized rabbit, Gyllenhaal is more than up for tackling one of his most internally tormented characters, even at a young age. In his hands, there's an innately preternatural quality to Darko that makes it clear how out of step he is with reality, and these elements of Gyllenhaal's performance aren't executed as caricature or mockery.

At the same time, there's a deeply lived-in quality to Gyllenhaal's portrayal of Donnie that grounds this character in some recognizable form of reality no matter how unhinged Kelly's script gets. There's a delicate balance between the eerie and the emotionally tangible within Gyllenhaal's work that's extraordinary to behold. It also doesn't hurt that the actor demonstrates effortless ease bouncing off the most conceptually preposterous elements of "Donnie Darko," like Frank the giant rabbit. Within these moments, Gyllenhaal demonstrates a proficiency for the ludicrous that would serve him well in later comedic roles in movies like "Okja." Though there's shades of future iconic performances in here, Jake Gyllenhaal's "Donnie Darko" work, even after all these decades, is still totally one-of-a-kind.

In so many of David Fincher's movies, from the worst to the best, this filmmaker takes pretty boy leading men and plunges them into darker territory. From Brad Pitt in "Fight Club" to Daniel Craig in "The Girl with the Dragon Tattoo" to Ben Affleck in "Gone Girl," it's a fascinating streak of subversive casting. Jake Gyllenhaal delivered some of his absolute greatest work continuing this trend with the 2007 Fincher film "Zodiac." In this chronicle of the manhunt for the Zodiac Killer during the 1960s and '70s, Gyllenhaal plays Robert Graysmith, a political cartoonist who becomes obsessed with tracking down the Zodiac's identity. This proves to be a descent into lunacy, as Graysmith keeps encountering one dead end after another. His persistent hunt for the truth drains him of energy, years of his life, and eventually, his family.

So much of "Zodiac" is about what's not on-screen, like the depiction of the Zodiac Killer tormenting his victims in which this grisly figure is not in the frame. But Gyllenhaal's front-and-center performance is also one of the film's greatest strengths, as he's always captivating whenever he shows up on-screen. He especially proves adept at finding varied and idiosyncratic ways of depicting Graysmith slowly becoming more and more obsessed with the case. There's a gradual transformation here that Gyllenhaal communicates with the tiniest bits of physicality. Once again, Fincher finds the grimy master thespian inside a conventionally attractive Hollywood leading man.

Psychological thrillers like "Nightcrawler" are not the easiest thing in Hollywood to pull off. Director Dan Gilroy's vision for this feature was always going to rest on Jake Gyllenhaal's convincing nature as Louis Bloom, a man who will do anything to get himself a steady, famous job in the television industry — including getting intrusive pictures of people in car accidents, break-ins, and other horrific events. As Bloom, Gyllenhaal is constantly, worryingly on edge. His portrayal of Louis Bloom is that of a man who never blinks; he's just always scheming and examining how a situation can benefit him. There's an inhumanity to him even as his personality traits chillingly remind viewers of so many real-life souls.

The aloofness and capitalistic desires of the bourgeoisie are made flesh and just a bit more overt than usual in Gyllenhaal's "Nightcrawler" work. This actor's immense dedication to this uneasy character, which resulted in Gyllenhaal needing stitches at one point, vividly comes through the screen and makes the movie's depraved world so compellingly tangible. Gyllenhaal's work gets extra captivating, as the plot spirals out of control and Bloom mostly continues to stick to his nonchalant attitude toward the well-being of others.

There's an unmoveable nature and consistency to this sociopath that Gyllenhaal keeps making unnerving from the first moment that audiences get a look at him. Louis Bloom is a richly detailed, eerie concoction who benefits mightily from the actor playing him. Gyllenhaal in "Nightcrawler" astonishes and gets under your skin effortlessly.