Jake Gyllenhaal has had an incredible career. Since beginning acting as a child in the 1990s, he's starred in award winners, cult classics, major blockbusters, and everything in between for a filmography that's as varied as it is entertaining. Here I'd like to look at twelve of the best films Gyllenhaal has appeared in and make a case for the greatness of each.
12. End of Watch (2012)
Before David Ayer became a meme for directing Oscar-winner Suicide Squad and Netflix's much-derided Bright, he directed and/or wrote some of the best Los Angeles-set crime films of the 21st century. End of Watch is the best of those he directed (he wrote Training Day and the first The Fast and the Furious). Much of its success is attributable to the fantastic central performances of Gyllenhaal and Michael Peña. They play LAPD cops who become targets of a powerful cartel after a bust. Told significantly in found footage style, the movie places audiences in the middle of the action during its shootouts and explores the two men's personal lives, including their friendship and romances.
11. Velvet Buzzsaw (2019)
Velvet Buzzsaw is a divisive movie, some find the ensemble horror-comedy overly silly and too on the nose in its satire of the art world, but I can't help loving it. The film tells the story of several characters in the art world who discover the paintings of an incredibly talented shut-in after his death and begin to profit from his work. Soon though, more and more people who have attempted to make money from the art start dying in supernatural ways related to art. It's an undeniably silly and over-the-top movie (Gyllenhaal's performance as a very flamboyant bisexual art critic certainly doesn't ground the film), which is precisely why it's so much fun.
10. Enemy (2013)
Any movie that requires an actor to play two (or more) roles is already making a bold move. Will the actor be able to play the different characters in a way that makes each of them believable as distinct characters? Will the performances be overcranked to ensure the audience knows which character they're seeing at any given time? In the case of Enemy, in which Gyllenhaal plays a professor who discovers an actor identical to him and investigates, Gyllenhaal manages to succeed fantastically. His performances as both the professor and the actor are grounded and real but distinct enough that the audience always knows who they are watching. It's a remarkable performance at the center of a great psychological thriller that asks more questions than it offers answers.
9. Jarhead (2005)
Based on Marine Anthony Swafford's memoir of his time in the Gulf War, Jarhead is a war movie unlike any other. Instead of delivering visceral and brutal scenes of war violence, the film chronicles the debilitating boredom that many soldiers faced during that conflict, including Swafford, played in the film by Gyllenhaal. It's a powerful movie that examines the myriad ways that war is horrific and wears people down, whether they are engaged in violence or not. It also doesn't hurt that the film looks beautiful courtesy of famed cinematographer Roger Deakins.
8. Brokeback Mountain (2005)
One of the most legendary Oscar snubs of the modern era is Brokeback Mountain losing Best Picture to Crash. One of those films is now considered an embarrassing and mishandled exploration of race, while the other remains a classic film about queer desire, repression, and masculinity. Based on a story of the same name by Annie Proulx, Brokeback Mountain tells the story of two sheepherders (Gyllenhaal and Heath Ledger) who begin a sexual relationship while on a job that develops into a lifelong romance. It's a devastating and beautiful film full of great performances from the two leads and the supporting cast, including Anne Hathaway and Michelle Williams as the most significant women in their lives.
7. The Sisters Brothers (2018)
A very different western from Brokeback Mountain, The Sisters Brothers is a period western set in the early 1850s. Based on the novel of the same name by Patrick deWitt, the film follows a pair of bounty hunter brothers (John C. Reilly and Joaquin Phoenix) as they search for a couple of gold hunters, played by Gyllenhaal and Riz Ahmed. What makes The Sisters Brothers remarkable is the incredible tenderness in many of its characters, including Gyllenhaal's John Morris. It's a Western that features all of the matter-of-fact violence required by realistic films about the wild west. Still, it's not overburdened by grimness or seriousness and includes moments of natural levity and sweetness.
6. Ambulance (2022)
One of Michael Bay's best films and arguably a return to form after years of CGI-heavy Transformers films (which, to be clear, I mostly love), 2022's Ambulance is two hours of adrenaline-pumping action. A remake of a Danish film of the same name, the movie follows two bank-robbing brothers who hijack an ambulance with an EMT and a cop that one of them shot, who they are all now desperately trying to keep alive while also outrunning the cops on their tail. The movie takes audiences on tour through downtown and Eastern LA, featuring some of the most breathtaking Bayhem of the action auteur's career. And yet, Gyllenhaal, Yahya Abdul-Mateen II, and Eiza González keep the film grounded in human relationships and emotions as the brothers and paramedics in the eponymous ambulance.
5. Prisoners (2013)
Gyllenhaal made two films with Denis Villeneuve in 2013, Enemy and Prisoners. The fact that they both land on this list of his greatest films speaks to how well the actor and director collaborate. In Prisoners, Gyllenhaal plays a police detective investigating the disappearance of two young girls, the daughters of Hugh Jackman and Terrence Howard's characters, who have taken matters into their own extralegal hands.
Prisoners is a difficult movie to watch, as it centers on child abduction and abuse, but it's also a rewarding film that grapples with the lengths to which parents will go to protect their children.
4. Donnie Darko (2001)
The movie that made Gyllenhaal a household name, Donnie Darko took a couple of years to become the celebrated cult classic it is today. But it was always going to become a beloved film. Gyllenhaal plays the eponymous Donnie, a disaffected teenager with visions of a man in a rabbit costume who tells him the world will end.
It's a science fiction, coming-of-age film that can be watched as a puzzle movie, drama, or both. The film doles out enough lore to fit together all of its pieces. But the mystery is part of what makes it so enduring, especially since that mystery allows the focus to remain on the genuine emotion at the heart of the film.
3. Zodiac (2007)
Of course, appearing in David Fincher's best film (that's right) ensures that it will land high on a list of the best movies in Gyllenhaal's career. Zodiac, which tells the true story of the serial killer who terrorized San Francisco in the late 1960s and '70s, follows crime reporter Paul Avery (Robert Downey Jr.), inspector Dave Toschi (Mark Ruffalo), and cartoonist Robert Graysmith (Gyllenhaal) as they all become fascinated by and central to the story of the Zodiac killer.
The movie is an amalgam of genres, from true crime to procedural and psychological horror movies. Fincher's deft direction and the strong lead performances ensure that this epic story never feels overlong or unsatisfactory, even though we still don't know who the Zodiac was.
2. Nightcrawler (2014)
Five years before the delightfully silly Velvet Buzzsaw, Gyllenhaal made this decidedly unsilly crime thriller about an ambitious local news videographer in Los Angeles with Buzzsaw writer/director Dan Gilroy. It's a testament to Gilroy's talent as a writer that he's not only able to satirize the art world but also create a palpably tense story of Lou (Gyllenhaal), a sociopath willing to do anything he can to get ahead in the cutthroat (almost literally) world of local news videography in a city like Los Angeles.
Gyllenhaal plays Lou in a way that's unnerving and sometimes outright scary but also manages to be charming and inviting in a way that makes it believable that the people around him are not constantly on edge. It's an astounding performance that many (myself included) believe should have won him an Oscar.
1. Nocturnal Animals (2016)
Perhaps a scorching hot take, but I firmly believe that fashion designer and director Tom Ford's adaptation of the novel Tony and Susan by Austin Wright is the best film in Gyllenhaal's filmography (thus far). The film tells two stories, one of a couple's initial courtship and ultimately deteriorating romance and another of the fictional novel one writes and sends to the other years after they separated. Gyllenhaal plays both the lead in the novel and the real-life story, while only Amy Adams plays the lead in the real storyline as Gyllenhaal's ex-wife, to whom he sent his new book.
The novel is pure pulp; it tells the story of a man whose wife and daughter are kidnapped, sexually assaulted, and murdered after the three are attacked, and he escapes. But the grounded tale of their romance is far from easy viewing as they fight against disapproval and struggle with money as Gyllenhaal's character is more dedicated to his work as a writer than anything else. Nevertheless, it's a stunningly beautiful movie, which makes sense for a film directed by a fashion designer, that contrasts the novel's violence with the wealth and art of Adams' character's life without her ex. It's not an easy movie, but it's one of the most beguiling films of Gyllenhaal's career, which is why I think it's the best.
Kyle Logan is a film and television critic and general pop culture writer who has written for Alternative Press, Cultured Vultures, Film Stories, Screen Anarchy, and more. Kyle is particularly interested in horror and animation, as well as genre films written and directed by queer people and women. Kyle has an MA in philosophy from Boston College, is a member of the Chicago Indie Critics, and along with writing, organizes a Queer Film Challenge on Letterboxd.