The 10 Best Jake Gyllenhaal Movies

Best Jake Gyllenhaal Movies - The Guilty (2021)

After Leonardo Dicaprio, one of the most recognizable actors globally on the internet is Jake Gyllenhaal. Coming from a lineage of great personalities in the film industry, the L.A.-born actor always manages to lead a good film.  You know it is a good film if Gyllenhaal stars in it. He is one of those actors, who, despite not being too method or drastically changing his appearance, creates compelling portraits, someone like Ethan Hawke or Nicolas Cage. While he has expressive eyes that go a long way for an actor, Gyllenhaal’s biggest strength is his ability to create spontaneous outbursts, some of which have become a part of modern pop culture. His filmography is diverse, not showing a proclivity for a specific type of role. His life has come a full circle with the Spider-Man movie, where has settled in without any noticeable hiccups. His natural ability as an actor is further embellished by his commitment to be observant and react to his co-actors. On the release of ‘The Guilty’, below is a list of some of his best works that you should enjoy.

Honorable Mention:

Southpaw (2015)


Southpaw is Gyllenhaal’s first role as an athlete and he leaves no stones unturned in transforming himself. He looks menacing as Billy Hope, the reigning heavyweight champion whose life falls apart when his wife is fatally shot at a fundraiser. But successfully playing Billy was not just about looking and boxing like a professional. The movie has profound themes of fatherhood, substance abuse, and self-redemption that require a balancing act between style and substance.

Gyllenhaal matches Billy’s professional aggression with his vulnerability in personal life for most parts. There are a few occasions when he does not look too convincing, but in his best moments, his Billy Hope is a burning remnant of De Niro’s LaMotta. Director Antoine Fuqua’s risk-less and predictable film is elevated by Gyllenhaal’s committed central performance, despite not landing all the punches as he quite intended to.

Watch Southpaw on Netflix

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10. Zodiac (2007)

Best Jake Gyllenhaal Movies - Zodiac (2007)

‘Zodiac’ is efficiently serviced by director David Fincher‘s love for creating stories that never quite come to a resolution but always come at the cost of his antiquated antihero’s sacrifice. Jake’s performance anchors the story and navigates it from the start to the end. He plays Robert Graysmith, a naive cartoonist, who takes a feverish interest in Zodiac, the serial killer who gave America many a sleepless night, as he joins hands with fellow journalist Paul Avery to find out the truth.

His portrait is based on a real-life journalist and author of the same name. ‘Zodiac’ does not squarely depend on Jake’s ability or tendency to pull out the odd magic trick but instead works as a function of Fincher’s well-calibrated and rigorous penchant as a filmmaker and keen eye for details. Graysmith’s character can be seen as an antihero, his story one of success. But his arc from the sweet, boyish cartoonist, to an obsessed, never-ending pursuer of dead ends is more tragic than it is triumphant.

Watch Zodiac on Netflix

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9. Donnie Darko (2001)

Donnie Darko (2001)

‘Donnie Darko’ has definitely established a cult following in recent years. Brushing aside the muted response on release, the Gyllenhaal-starrer has gained traction with the advent and popularity of new-age sci-fi films. Its mind-bending plot has a lot to offer, including nuanced performances from a young cast. Gyllenhaal stars as the titular character and shares screen space for the first time with sister Maggie. Donnie is a confused teenager, although qualifying it so is not necessary. In the process of trying to make sense of the world, he is burdened with making sense of all and more.

While commenting on the film, Gyllenhaal recently revealed how relatable the troubles of Donnie were to him at the time. His revelations point toward how his process of playing Donnie and getting to play him was a moment of perfection. Comparatively and understandably, Donnie is weaker than other Gyllenhaal performances in terms of theatric heft, becoming a bit loud and too eager at times, but is inherently more spontaneous and raw.

Watch Donnie Darko on Prime Video

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8. The Guilty (2021)

Best Jake Gyllenhaal Movies - The Guilty (2021)

The American remake of the Danish film of the same name is an exact replica: word for word. There is hardly any difference in how the remake is conceptualized. Save for Gyllenhaal’s earnest performance, Antoine Fuqua’s ‘The Guilty’ is tepid and derivative and offers nothing new on the Danish film. And even in the intimation, the remake loses the original’s compact setting and nervy pace, hardly creating any tangible tension with the same details and plotting. Gyllenhaal plays suspended police officer Joe Baylor, who finds himself on Comms duty till the hearing of his court case for the alleged shooting of an 18-year-old.

Baylor, like most Gyllenhaal characters, is broken from inside, suffering from intense, short bouts of a burning sensation inside, which is his guilt over the shooting. The actor characterizes Baylor with traits like a short temper and wearing his anger under his skin. Confronting oneself is one of the most terrifying and brave things we humans can do. Standing face first with the consequences of our actions, our moral compass guiding our reaction often leads to rewarding conclusions. The fire that spreads and rages in the setting outside, is matched by the immense pain that Baylor feels inside of him. And it all culminates with the core conflict of the story coming to a halt.

Watch The Guilty on Netflix

7. End of Watch (2012)

‘End of Watch’ refreshingly do-overs the buddy cop action drama and infuses in it the found-footage dimension of visual storytelling. Jake Gyllenhaal and Michael Pena star as two Los Angeles cops, who, during their normal patrol, find themselves in trouble, giving us a timely reminder of the kind of danger police officers put themselves in every day to protect us. Director David Iyer’s focus is more on the friendship between the two leads, rather than on violence.

‘End of Watch’ is distinguished from other procedural dramas as it sheds light on the tough lives people engaged in public welfare jobs lead. Having trained for five months with the LAPD, Gyllenhaal not only looks the part but also seems to have done a personality swap. He is almost unrecognizable in his role and shares fine chemistry with Pena on screen. The fine-tuned details in the dialogue and execution thrust past conventional wisdom and genre tropes that have so vigorously dictated procedural dramas hitherto.

6. Nocturnal Animals (2016)

 Nocturnal Animals

Irrespective of the angle from which you view the character of Tony Hastings, there is no way you would not end up labeling him the “sheep” of society. The wolf-sheep narrative that mostly defines the world as we know it today, plays heavily in Tom Ford’s plot inside the plot. The deception obviously is the way Adams’ character reads the story and not how actually things are. Gyllenhaal, probably for the first time, plays a character who is completely and utterly powerless, or as the romantics call such a person, vulnerable. It is often said that a man’s true measure is in the circumstance when he puts his family above him and guarantees their safety. And Hastings certainly does not live up to the standard. But what is even more engrossing about Edward and Tony collectively and the film, is that you realize that they both are living the same kind of lives, experiencing similar heartbreaks and emotions.

They are the same men represented differently through the former’s intrinsic artistic talent and the great pain he feels losing the love of his life. Hasting’s fate is also a byproduct of Edward’s process of grief and dealing with Susan’s decision to leave him that manifests in vile anger; discomforting and haranguing.

Gyllenhaal nails Hastings’ and Edward’s distraught emotional state. His representation is neither too pronounced, nor too understated that would vitiate the rare realism that Ford achieves. ‘Nocturnal Animals’ is a mesmerizing mouthpiece for director Tom Ford’s personal interpretation of Tony and Susan, the film’s literary inspiration.

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5. Wildlife (2018)

Best Jake Gyllenhaal Movies - Wildlife

There is a very interesting phrase that Maddox (Thomasin McKenzie) from M. Night Shyamalan’s ‘Old’ uses to describe the process of aging: “changing colors”. Realizing yourself and those around you as “people” – with real feelings, insecurities, and imperfections – is a unique, confusing challenge.

Most of ‘Wildlife’ is narrated and felt through this experience of Joe Brinson seeing his parents as not the picture-perfect, doughy couple from his childhood. They fight a lot; swear at each other; often disagree on how to do things, and for once, do not have Joe as the center of their lives. Although it is natural and easier to think of Jerry and Jeanette’s troubled marriage as the pivot in the scheme of things, Joe is never on the sidelines. His perspective is always the guiding light for the viewer. It is really Paul Dano’s artistic maturity that elevates the film to be multi-dimensional and deal with a lot of themes, on an individual level and on a familial level as well.

Jake’s character, I think, is in some ways like Sir Gawain from ‘The Green Knight‘. He is not defined by the person he is or wants to be, but by conventional wisdom about manhood and the mold of a quintessential father, husband. His pride trumps any personal longings or ambition he ever had. He loses sight of himself in the process of absorbing this cultural nuance. But it is also hypocritical of him to then pass on the mantle of being the man of the house to his teenage son.

There is no surprise then that he feels lost and dysfunctional. And that is what makes his character so real. It is a pity that Gyllenhaal and Mulligan, two of the most prolific actors of their generation, do not share more screen space. They are absolutely terrific together, matching their synergies to make the film feel whole. Jake’s remarkable act of trying to look from the outside in and running away from the phantom of expectations that chases him around strikes the perfect balance of melancholy and tenderness.

4. Enemy (2013)

Enemy (2013)

Dennie Villeneuve’s ‘Enemy’ is a gorgeous head-scratcher. While the mind-numbing plot may be beyond us, Jake’s superlative twin performances are certainly not. There have been a lot of actors who have played two diametrically opposite characters in personality on screen like Tom Hardy, Mark Ruffalo, among others. Jake plays Adam and Anthony; the former is a quiet and shy college professor, the latter an outgoing actor. You have seen more of him as Adam in previous roles but his turn as Anthony is equally engaging.

His mix of subtlety and style creates a jarring dichotomy between his character and its subconscious. Director Villenuave also emphasized the theme of the film to explore the challenges in dissecting the human thought process; separating the man from his mind. For Jake, though, it was all about playing the two sides of a coin. Despite the physical similarities, the two men have no convergence in terms of personality. Even their worldview is uniquely different. As things turn out, the two seem to end up in their correct places; places where they rightfully belong.

Watch Enemy on Prime Video

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3. Prisoners (2013)

Best Jake Gyllenhaal Movies - Prisoners (2013)

Jake makes carrying his weary, obsessed self across ‘Prisoners’ effortless. He is so seamlessly integrated into his character’s skin and his turbulent state of mind that he makes the brilliant cast look downright average. Detective Loki’s stoic nature, in contrast to the chaos that unwinds around him, is a steady anchor that balances ‘Prisoners’ energies out. His ticks – blinking, rubbing his ring – more so give the impression that he is constantly thinking and drifting away further from where he wants to be.

Law enforcement’s chequered history at solving cases, including Loki’s own, is a constant source of palpable tension that flares when converged with the anger of a grieving parent. It is reflected in how gradually his energy and demeanor changes through the runtime. Jake’s committed performance is intense and marked by a strange sense of desperation that pushes him in the investigation beyond just professional obligations. His objective is on a human level to save a life by investing his personal space leaving little distinction between the two.

Watch Prisoners on HULU

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2. Brokeback Mountain (2005)

Brokeback Mountain

Jack Twist was a bold choice back when the film was made. So was Ennis. Homosexual characters were not as popular as they are now. Nobody wanted to play them and now all one wants to play are gay characters. Ledger and Gyllenhaal play two characters looking to be loved and feel liberated when doing so. Ang Lee does a terrific job of subverting the expectation of individuality and identity crisis, instead highlighting the tremendous capacity for the human heart to desire and feel love.

Gyllenhaal plays the more open character, who struggles lesser with his sexuality than Ledger’s, who is more tacit. This gives the actor the freedom to go off the charts and express his emotions more freely. Much like his earlier works, Gyllenhaal shows potency in handling complex emotions like a person of his age would. His performance is really inclined towards making you feel more than think, something that Ledger’s Ennis does.

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1. Nightcrawler (2014)

Best Jake Gyllenhaal Movies - Nightcrawler

Jake’s most compelling work comes as Lou Bloom, an intelligent sociopath, who begins night crawling as a stringer for a local television station after discovering his fascination for it. Under Dan Gilroy’s enabling direction, Jake grows Bloom’s personality from a well-spoken, adequately informed, and seemingly resourceful petty thief, to a soulless vulture selling people’s tragedy for heavy paycheques, with care and purpose. Every time Bloom finds a “picturesque” frame on the job – including the time moving a victim of a bloody car accident – his eyes light up like a five-year-old seeing his favorite toy. Despite the macabre reality of the plot, ‘Nightcrawler’ also has a comedic element that Jake executes so well that it lends a certain innocence to Bloom. Like when he runs from the Granada Hills house and lectures Ric on taking initiative or the time he sells a stolen bike with fast-talking, complex, untrue details.

The emancipated frame and tied-back hair really make the crazy eyes pop, an essential component in Bloom’s portrait. Just like any sociopath, Bloom keeps himself neat and has a clockwork-like work rigor. Jake’s creation of Bloom and his untamed, wild spirit springboards on Dan Gilroy’s magnificent writing. Reading the script, the dialogue really jumps out at you and also gives you a sense of how well Jake and Gilroy worked together to articulate Bloom’s character and the broader theme of unethical modern-day journalism. Jake’s biggest success with Bloom is that, in retrospect, there is hardly any person who, without knowing what he really does, would be able to resist engaging with and getting drawn in by his charm.

The charm that he spews masks his venomous insides for people. On the customary rewatch, I found a hard-hitting Bloom dialogue. “What if my problem wasn’t that I don’t understand people but that I don’t like them?” It instantly reminded me of Daniel Plainview’s similar remark in There Will Be Blood (2007). The two characters not only share a similar worldview but also establish themselves on the back of smart work and innate talent. Both live their lives as con-men, bent on taking and taking from other people on the promise of giving them false hope. Lou Bloom is the quintessential antihero today’s generational moviegoers have come to worship. Jake Gyllenhaal delivers a resounding performance that is in equal parts as shocking, as it is a living truth of the society.

Watch Nightcrawler on Netflix

Arnav Srivastav

Self-effacing and self-absorbed. College at RGNUL. A Cùle forever. Driven, ambitious, and "I hate most people". Oh, and I love movies if that wasn't obvious.