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Jake Gyllenhaal has had prominent roles in an impressive number of cinematic gems, but here's a ranking of his best crime genre films (including 2021's The Guilty), from his worst to his best. The 40-year-old actor is a household name these days, but he was starring in films before he was even a teenager. Since then, he's been in monstrous hits like Donnie Darko, Prisoners, Nightcrawler, Brokeback Mountain, Jarhead, and more.

Like with anyone in his field, certain movies on Gyllenhaal's list of credits are better than others and have evangelized more fans to his work than some of his other titles. Regardless, he's proven to have an innate ability to transform into whatever characters he plays, whether they're a troubled and angsty teen in a sci-fi thriller (the titular Donnie Darko) or an almost sociopathic-seeming man who bounces between crime scenes to pay his bills via news coverage (Lou in Nightcrawler). Impressively, he's performed these various roles throughout a diversity of genres.

Jake Gyllenhaal played the villain Mysterio in Spiderman: Far From Home, and he's even been in romantic comedy and drama flicks like Love and Other Drugs and Accidental Love. However, his best work -- where his talent really shines the most -- is within the crime drama genre. He's had a handful of films in this department over the years, and they're all certainly worth mentioning.

The Sisters Brothers (2018)

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2018's The Sisters Brothers is a quirky Western set in 1851. Directed by Jacques Audiard, it stars John C. Reilly and Joaquin Phoenix as Eli and Charlie Sisters, two brothers, both notorious assassins, who are hired to kill a man. Gyllenhaal plays a private detective named John Morris, who's tasked with tracking down the unlucky soul that the violent brothers seek and serving him up to them. The actor can always be counted on to deliver a more-than-up-to-par performance, and he certainly does so as Morris. In a film that showcases some of the Old West's nastier, unsavory elements, the compassion and morality he shows by refusing to hand Hermann Warm (Riz Ahmed) over to the two titular siblings is striking. The Sisters Brothers has its flaws, one of which is how its quirkiness doesn't always fit with the overall tone. Despite this, as well as the fact that this Jake Gyllenhaal-featuring film happened to be a bit of a box office flop, it's worth a watch. The cast alone beckons to cinephiles, and the piece can also very well be suited for anyone who likes Tarantino-esque oddity and wild, messy, and well-choreographed gunfights.

End Of Watch (2012)

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2012's End of Watch is a project from director David Ayer. Gyllenhaal plays LAPD police officer Brian Taylor, and the incredibly raw cop drama chronicles his daily life as he serves the crime-riddled city with his partner, Michael Pena's Officer Zavala. Since a sizeable portion of the film is presented as found footage from a documentary that Taylor is working on, it's a fresh take on the cop-centered concept that so many movies have delved into over the years. Even the drama's more conventional moments function as unflinching, informational glimpses into the day-to-day life and sense of camaraderie between officers like the film's two main men. Armed with a fitting movie soundtrack, End of Watch paints a much more realistic picture than one with an agenda. It doesn't hold back with moments that make its main characters seem unethical or juvenile, but it also shows instances of true heroism and dedication to the job.

Overall, it's an effective project, one where Gyllenhaal's acting prowess and character immersion shines. It's been widely documented that he spent months observing real-life LAPD officers while preparing for his role as Taylor, and that up-close-and-personal research certainly seems to add an extra layer of authenticity in a project that's already incredibly honest in its storytelling. Although End of Watch isn't Gyllenhaal's best role, this David Ayer movie is still a solid list entry.

The Guilty (2021)

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The Guilty is a Netflix police drama that, in addition to the streaming platform, released to select theaters. The crime thriller, which is a remake of the 2018 Danish film of the same name, hits Netflix on October 1. It's directed by Antoine Fuquan and written by famed True Detective creator Nic Pizzolatto - and the impressive creative team behind it shows. Gyllenhaal stars as Joe Baylor, an LA 911 dispatcher who's recently taken on the new role after being sidelined as a police officer due to controversy. He's familiar with conversing with people he has on the line, but a wild turn is taken when a woman calls in and conveys that she's in terrible danger.

As with all of the movies on this list, and other roles within different genres, Gyllenhaal shines as his character. He not only steals the show in the well-reviewed film because he's The Guilty's protagonist-on-a-mission, but also because of the inherent believability he imbues each line, facial expression, and his overall presence with as he desperately attempts to save the distressed woman from peril. The thriller is quite effective in how it takes the audience on a psychological goose chase along with Baylor. And when its shocking twist is revealed, it's time for those on the screen and those watching it to reevaluate everything. The way topical, but thoughtful, commentary on police brutality is woven into The Guilty's fabric is also one of the many reasons that this film is higher than a few other entries on the list.

Zodiac (2007)

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Director David Fincher knows his way around movies that are gritty, murder-laden, and downright great. 2007's Zodiac is one of the best examples of this. Though the serial killer drama clocks in at a lengthy 157 minutes and covers roughly a decade's worth of key events, it's an engrossing watch until the credits roll. Gyllenhaal plays real-life San Francisco Chronicle cartoonist Robert Graysmith, one of the press/law enforcement members that the movie follows as they tenaciously try to catch the infamous "Zodiac Killer," a mysterious identity who terrorized Bay Area, CA throughout the 1960s and '70s.

Gyllenhaal appears alongside a slew of big stars as he makes Graysmith's quirky, perpetually jittery, and extremely likable main character slowly cross the border into obsession while working to unmask the Zodiac's identity in his spare time. As previously mentioned, this real-life-inspired crime movie is a long watch. There's definitely a great deal of information condensed into one piece. Sometimes it's confusing with all of the different names and locations to keep straight. However, overall, the film's length and hefty amount of information allow viewers to understand a small fraction of the frustration that law enforcement must've felt while chasing the infamous killer. The lack of communication and overall coordination between different cities' police forces during the featured time period is almost infuriating to watch.

Nocturnal Animals (2016)

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Gyllenhaal plays two different, yet symbolically similar characters in the 2016 slow-burn psychological thriller Nocturnal Animals. He stars as Edward Sheffield, a sensitive writer who's become estranged from his ex-wife (played by Amy Adams). Out of seemingly nowhere, he sends her a manuscript of his newest novel. From there, Edward's ex embarks on an emotional, introspective-type journey as she navigates the book's events, which are depicted as a sub-plot where Jake Gyllenhaal also plays the movie character of grieving, vengeance-seeking family man Tony Hastings.

A heavily symbolic and purposely unnerving film, its subject matter is incredibly weighty, dealing heavily with betrayal, losing one's family, regret, gritty violence, and, of course, retribution. Some of its symbolism is a tad heavy-handed (like a featured painting that literally says "REVENGE" in huge letters), but, overall, its thoughtful and artsy nature is well-executed and effective. Along with co-star Michael Shannon, Gyllenhaal undeniably steals the show in Nocturnal Animals. His portrayal of deep-feeling Edward evokes painful amounts of empathy from the audience. It's equally as powerful as the way he inhabits Tony's despair-filled character.

Prisoners (2013)

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2013's Prisoners definitely tops this list of Gyllenhaal-featuring crime films. One of the high-quality projects you'd expect from director Denis Villeneuve, the thriller focuses on the hunt for two young girls that were kidnapped out of seemingly thin air in a relatively quiet Pennsylvania town. The legal side of this gut-wrenching investigation is handled by Gyllenhaal's Detective Loki. Likeable and noble, it's sad to watch the case become personal for him, as well. The film is great at eliciting sympathy for its characters, regardless of the circumstances.

Hugh Jackman's character of Keller Dover is another great example of this. Though his actions are highly unethical and illegal when he's holding a suspected kidnapper against his will to torture him for information, he's all out of options. His desperation about finding his daughter is palpable, as is the darkness of both the film's visuals and subject matter. Child abduction is a majorly anxiety-inducing threat in the modern world, and Prisoners taps into that fear directly in how it portrays the horror of the grim and nerve-wracking situation the girls' families find themselves in. The project is also imbued with a definite symbolic/philosophical nature. Examples of this include the movie's "labyrinth" and the antagonist's "war on God." Despite its bleak darkness, this neo-noir drama is often regarded as one of Denis Villeneuve's best movies, as well as a high point in Jake Gyllenhaal's career.