Since the 1990s, Jake Gyllenhaal has consistently graced the silver screen in a variety of films, such as Donnie Darko, The Day After Tomorrow, and Jarhead. Gyllenhaal made his first big-screen debut playing Billy Crystal’s son in the 1991 comedy City Slickers and his career took off several years later after appearing in October Sky.
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Gyllenhaal has surprisingly only received one Oscar nomination, but he continues to showcase his talent and range with each new role he takes on. From mind-bending flicks like Enemy to genre classics like Nightcrawler, the actor has proven that he can carry a diverse range of roles. Fans who are eager to see more of the talented actor’s work can turn to Gyllenhaal’s highest-rated movies based on their scores on Rotten Tomatoes.
20 ‘Enemy’ (2013)
Rotten Tomatoes Score: 72%
Image via Entertainment One
Adam Bell is a college history professor living in Toronto who decides to check out a film recommended by a colleague, and while watching, he notices that one of the actors looks exactly like him. Interested in learning more about the actor, he searches for him online, and what started out as simple curiosity turns into an obsession as Bell digs into the other man’s personal and private affairs.
Gyllenhaal stars in a dual role in the surrealist psychological thriller, Enemy, which is loosely based on the 2002 novel, The Double, written by José Saramago. The A24-produced film earned generally positive reviews, praising Gyllenhaal’s impressive double performance, which The New York Times called “subtle and fun,” and exceptional direction by director, Denis Villeneuve.
Enemy
Release Date February 6, 2014
Director Denis Villeneuve
Runtime 91 Minutes
19 ‘Everest’ (2015)
Rotten Tomatoes Score: 73%
Image via Universal Pictures
In May 1996, several expeditions to the summit of Mount Everest and are preparing to climb to the top of the highest point on Earth. Chief guide, Scott Fisher (Gyllenhaal), leads one group, which consists of experienced climber, Beck Weathers (Josh Brolin) and several others, along with a second group led by Rob Hall (Jason Clarke). When an unexpected storm strikes, the groups are caught in some of the most extreme blizzard conditions and must endure blistering winds and below-freezing temperatures in order to survive.
Everest is a survival adventure film based on the real-life events surrounding the Mount Everest disaster in 1996 and features an ensemble cast including Robin Wright, Keira Knightly, and Sam Worthington. Gyllenhaal is effortlessly captivating as Fisher who is determined to survive in order to see the birth of his first child, implementing high personal stakes into the suspense-filled plot.
Everest
Release Date September 10, 2015
Runtime 150
Main Genre Drama
18 ‘The Guilty’ (2021)
Rotten Tomatoes Score: 74%
A remake of the 2018 Danish film of the same name, The Guilty follows Joe Baylor (Gyllenhaal), a troubled police officer who has been demoted to work at the emergency call center. One night, Joe receives a distressing call from a woman named Emily (voiced by Riley Keough), who claims she has been kidnapped. As Joe tries to assist her and figure out her location, he becomes increasingly obsessed with solving the case.
The prospect of yet another American remake of a well-received foreign film may make moviegoers uncomfortable, but The Guilty is a marvelously well-made movie on almost every level, with a strong lead performance from Gyllenhaal. Moreover, since much of the dread is found in what is not seen on screen, people who can use their imagination will be able to appreciate this movie the most.
The Guilty (2021)
Release Date September 24, 2021
Runtime 1 hr 30 min
Watch on Netflix
17 ‘Nocturnal Animals’ (2016)
Rotten Tomatoes Score: 74%
Adapted from the novel Tony and Susan by Austin Wright, Nocturnal Animals is a psychological thriller directed by Tom Ford. It tells the interconnected story of Susan Morrow (Amy Adams), an art gallery owner, and her ex-husband Edward Sheffield (Gyllenhaal), who sends her a manuscript titled “Nocturnal Animals,” which he dedicates to her. As Susan reads the novel, the film alternates between her real-life experiences and the fictional story within the manuscript.
Ford evokes the frustrations of our ridiculous world and feeds the audience a feast of metaphors and cinematic language with superb color, style, and technique. Moreover, despite the film’s stunning façade, its emotions are nonetheless strong, unsettling, and occasionally captivating. Additionally, Gyllenhaal shines in his natural tendency to fully express the psychology of his characters without exerting too much effort, leaving the audience frightened.
Nocturnal Animals
Release Date December 9, 2016
Director Tom Ford
Runtime 116 minutes
16 ‘Prisoners’ (2013)
Rotten Tomatoes Score: 81%
Image via Summit Entertainment
Prisoners revolves around the kidnapping of two young girls in Pennsylvania and the accompanying police search for the alleged kidnapper. The father of one of the daughters takes matters into his own hands when police apprehend a minor suspect and release him. Gyllenhaal portrayed Detective Loki, a police officer working on the case.
While its protagonists are trapped in its devastating narrative maze, Prisoners is an engaging thriller that knows how to harness its emotional force. Gyllenhaal, along with Hugh Jackman and Paul Dano, delivered powerhouse performances that are so haunting and heartbreaking even when the film ends. Jackman’s portrayal of Keller Dover, in particular, is an unforgettable reminder of how far parents will go to protect their kids.
Prisoners
Release Date September 18, 2013
Director Denis Villeneuve
Runtime 153
Main Genre Crime
15 ‘The Good Girl’ (2002)
Rotten Tomatoes Score: 82%
The Good Girl centers on a young, married woman (Jennifer Aniston) whose routine life is turned upside down when she begins an illicit, passionate relationship with a strange stock guy (Gyllenhaal) at a bargain store who believes he’s Holden Caulfield.
Gyllenhaal was a significant part of the movie, taking the cliché of an enraged young guy immersed in Holden Caulfield and giving it real depth. Moreover, The Good Girl is a moving, perceptive, and genuinely enjoyable film that brings viewers to the intersection of the human heart while Aniston gives one of the best performances of her career.
The Good Girl
Release Date January 12, 2002
Runtime 94
Main Genre Comedy
Watch on Paramount+
14 ‘Guy Ritchie’s The Covenant’ (2023)
Rotten Tomatoes Score: 84%
Image via MGM
Taking place during the Afghanistan War, Guy Ritchie’s The Covenant follows US Army Sergeant John Kinley (Gyllenhaal) who was saved by an Afghan interpreter Ahmed (Dar Salim) after an ambush. When Kinley discovers that Ahmed and his family were not provided with safe passage to America as promised, he must attempt to make good on his commitment by going back to the conflict area to get them before the Taliban start looking for them.
The Covenant departs from Guy Ritchie’s previous works in that it places a strong emphasis on character development and tackles much more weighty topics. Furthermore, it is Gyllenhaal’s most secure part, giving Salim more room to shine in a bigger lead than most of his Hollywood roles have so far.
Watch on Amazon Prime
13 ‘End of Watch’ (2012)
Rotten Tomatoes Score: 85%
Image via Open Road Films
End of Watch follows two officers, Brian Taylor (Gyllenhaal) and Mike Zavala (Michael Peña), from the South Central District of the Los Angeles Police Department. The film focuses on their routine police work, their interactions with a particular gang, their camaraderie, and their interpersonal relationships.
End of Watch is not a typical cop-partner/buddy movie; it is instead exciting, fast-paced, and has solid performances by Gyllenhaal and Peña. The intensity of the work details, as well as the emotional toll it has on the cops, are beautifully captured in the movie. Also, the distinction between the viewer and the actors is blurred as the camera switches between their point of view and the audience.
End of Watch
Release Date September 20, 2012
Runtime 109
Main Genre Crime
12 ‘Okja’ (2017)
Rotten Tomatoes Score: 86%
Okja follows a little girl Mija, (Ahn Seo-hyun) who nurtured the titular genetically modified super pig and decides to set out on a mission to save the pig from abuse at the hands of the meat industry after being sent to America. Gyllenhaal portrayed the psychopathic zoologist and TV personality, Johnny Wilcox.
As a ridiculously behaved nature expert who is taken advantage of by the meat lobby, Gyllenhaal gives the most unrestrained performance of his career in the film. Although Okja occasionally deviates between action and comedy, horror and social critique, it never stops being bold, becoming a lightly satirical look at how we produce meat in real life.
Okja
Release Date June 28, 2017
Director Bong Joon-ho
Cast Tilda Swinton , Sheena Kamal , Michael Mitton , Colm Hill , Kathryn Kirkpatrick , Jose Carias
Runtime 120 minutes
11 ‘Lovely & Amazing’ (2001)
Rotten Tomatoes Score: 86%
Lovely & Amazing centers on Jane (Brenda Blethyn), an affluent matriarch and a mother of three daughters who seems to have little in common other than a weird kind of idealism. Every one of the women searches for redemption in her own haphazard manner, but any relief they do manage to achieve is deceptive and transient.
Jordan, played by Gyllenhaal, is a youthful one-hour photo developer who wins the adulterous devotion of his irate and much older coworker, played by Catherine Keener. Gyllenhaal expertly depicts the youthfulness, curiosity, and yearning to start relationships with older women with his limited screen time. Moreover, though Lovely & Amazing didn’t do well at the box office, it explores her characters’ psyches in depth while capturing the body-image anxieties of women.
Watch on Tubi
10 ‘Donnie Darko’ (2001)
Rotten Tomatoes Score: 87%
One night, high schooler, Donnie Darko (Gyllenhaal) sleepwalks out of his house and meets a giant, demonic rabbit named Frank who tells him that the world’s going to end in 28 days. As Donnie continues seeing Frank, his parents send him to see a psychiatrist begging the question, is Donnie living in a parallel universe, or is this all in his head?
Donnie Darko is a chilling and mind-bending sci-fi movie that not only explores the theory of alternate universes but also the alternate lives that some manage to lead behind closed doors. This psychological thriller stars Gyllenhaal alongside his sister, Maggie Gyllenhaal, as well as Drew Barrymore, Patrick Swayze, and a then-unknown Seth Rogen. In 2021, director and writer, Richard Kelly, announced that he has plans for a sequel that will expand on the film’s universe.
Donnie Darko
Release Date October 26, 2001
Director Richard Kelly
Cast Jake Gyllenhaal , Holmes Osborne , Maggie Gyllenhaal , Daveigh Chase , Mary McDonnell , James Duval
Runtime 113
Main Genre Drama
9 ‘The Sisters Brothers’ (2018)
Rotten Tomatoes Score: 87%
During the Gold Rush, Eli (John C. Reilly) and Charlie (Joaquin Phoenix) Sisters are infamous gunslingers who are hired to track down and kill a chemist traveling to California. As the brothers venture through the Northwest, they encounter unpredictable dangers and experience setbacks that put their brotherly bond to the test. Gyllenhaal played John Morris, a private detective, who is hired by the Sisters to track down the said chemist.
The Sisters Brothers is a modern Western that remains true to the genre with dark humor and an excellent lineup of leading men. While the film was unsuccessful at the box office, it’s worth seeing just for the overall captivating performances that carry this refreshing new tale of the Wild West, making it one of the most underrated Westerns of the 21st century.
The Sisters Brothers
Release Date September 19, 2018
Director Jacques Audiard
Runtime 121
Main Genre Western
8 ‘Brokeback Mountain’ (2005)
Rotten Tomatoes Score: 88%
Jack, played by Gyllenhaal, a rodeo cowboy and ranch hand, Ennis (Heath Ledger) are hired to herd sheep for the summer grazing the herd on Brokeback Mountain. The two men realize they have deeper feelings for one another and develop a relationship but when they return home, they try to go their separate ways. Despite trying to move on, they are unsuccessful and secretly continue their relationship for two decades.
Directed by Ang Lee, Brokeback Mountain is a romantic Western that highlights the beautiful and heartbreaking aspect of star-crossed lovers. Before Gyllenhaal and Ledger signed on, casting approached other notable stars including Brad Pitt, Leonardo DiCaprio, and Matt Damon, but despite all loving the script, no one could commit. The movie earned several Oscar nominations and went on to win Best Director, Best Adapted Screenplay, and Best Original Score.
Brokeback Mountain
Release Date September 10, 2005
Runtime 134
Main Genre Drama
7 ‘Stronger’ (2017)
Rotten Tomatoes Score: 90%
Jeff (Gyllenhaal) is cheering for his girlfriend who is running in the Boston Marathon, but before she can cross the finish line, a bomb explodes, knocking Jeff out. When he wakes up, he learns that he’s in the hospital and that they had to amputate both of his legs. On top of the strenuous road ahead of him, Jeff manages to remember enough of the bombing to describe the suspect resulting in the arrest of one of the bombers.
Stronger is a movie based on the unbelievable true story of Jeff Bauman, who survived the 2013 Boston Marathon bombings and was hailed a hero after assisting authorities in the arrest of one of the bombers. The movie is an emotional and raw view into the aftermath of not only Bauman’s life but also others who were impacted by the attack. Gyllenhaal shows his natural talent and outperforms in this role.
Watch on Amazon Prime
6 ‘Zodiac’ (2007)
Rotten Tomatoes Score: 90%
Image via Paramount Pictures
In 1969, San Francisco’s terrified by an unknown killer known as The Zodiac who communicates with authorities and the media through cryptic letters. As the madman continues collecting victims, cartoonist, Robert Graysmith (Gyllenhaal), manages to decipher one of the letters and dives head-first into a decades-long search for the killer’s identity.
Directed by David Fincher, Zodiac is an adaptation of the novel written by Graysmith who spent years working extensively on the case. Gyllenhaal delivers a brilliant performance alongside Robert Downey, Jr., Mark Ruffalo, Brian Cox, and Dermot Mulroney. While the case remains unsolved, Fincher compensates with a detailed layout of facts that are enough to satisfy audiences in the end.
Zodiac
Release Date March 2, 2007
Runtime 157 minutes
5 ‘Spider-Man: Far From Home’ (2019)
Rotten Tomatoes Score: 90%
Image via Marvel Studios
Peter Parker (Tom Holland) was hoping to enjoy his school vacation abroad, but when entities from another universe start to terrorize our world, Nick Fury arrives to ask for the young hero’s help. Despite still mourning the loss of Tony Stark, Spider-Man eventually teams up with the new S.H.I.E.L.D. agent, Mysterio (Gyllenhaal) only to learn that there is more to the new superhero and his origin story.
Spider-Man: Far From Home is the final film in phase three of the MCU and was Gyllenhaal’s first appearance in the franchise. During an interview on The Howard Stern Show, Gyllenhaal said he was overwhelmed on the first day of filming and struggled to remember his lines. The actor managed to gain his composure and relax after reassuring words from Holland, which soon led to him becoming one of the best villains in the MCU.
Spider-Man: Far from Home
Release Date June 28, 2019
Runtime 130
4 ‘October Sky’ (1999)
Rotten Tomatoes Score: 91%
In West Virginia, Homer Hickman (Gyllenhaal) expected to follow in his father’s footsteps as a coal miner but after seeing the launch of Sputnik 1, he becomes interested in rock science. His father disapproves of his son’s new interest but with the help of his friends and a supportive teacher (Laura Dern) he pursues his dream of earning a science scholarship and a ticket to a better life.
October Sky marked Gyllenhaal’s first time playing a lead role and was universally praised for his performance. The movie is an adaptation of the novel Rocket Boys written by Homer Hickman Jr. The title of the film is clever and unique as it’s an anagram of the novel’s title as well as a nod to the original broadcast description of Sputnik 1.
Watch on Amazon Prime
3 ‘Source Code’ (2011)
Rotten Tomatoes Score: 92%
After a train explosion, Colter (Gyllenhaal) must figure out the identity of the bomber to prevent the possibility of another attack. He joins a top-secret military operation that allows him to live the last few minutes of a man who was killed in the event. As Colter unravels the final moments, he knows he can complete his mission but only if he has enough time.
Source Code is a science-fiction thriller directed by Duncan Jones who was approached by Gyllenhaal to direct the movie after seeing Jones’ film,Moon. The movie has been compared to Tony Scott’s Déjá Vu, but Source Code takes the complex concept of dreams and time traveling to a whole different level in this fractured storytelling feature.
Source Code
Release Date April 1, 2011
Director Duncan Jones
Runtime 93 Minutes
2 ‘Wildlife’ (2018)
Rotten Tomatoes Score: 94%
Jerry (Gyllenhaal), his wife, Jeanette (Carey Mulligan), and their son, Joe have recently moved to a small town in Montana near the Canadian border. When Jerry loses his job, tensions rise between the couple and come to a head when he decides to join firefighters tending to a forest fire leaving his family to fend for themselves.
Directed by The Batman’s Paul Dano, Wildlife is a beautiful movie adaptation of the 1990 novel of the same title written by Richard Ford. Gyllenhaal co-produced with Dano who also co-wrote the script with actor and partner, Zoe Kazan. The movie earned positive feedback from critics, who considered it to be a touching piece of filmmaking that heavily relied on drama.
Wildlife
Release Date January 1, 2019
Cast Ed Oxenbould , Jake Gyllenhaal , Carey Mulligan , Travis W Bruyer , Zoe Colletti , Tom Huston Orr , Bill Camp , Darryl Cox
Runtime 105 Minutes
Main Genre Drama
Watch on Tubi
1 ‘Nightcrawler’ (2014)
Rotten Tomatoes Score: 95%
Image via Open Road Films
Nightcrawler follows Lou (Gyllenhaal), a petty thief, who makes a career change and pursues a job as a cameraman. With a camcorder and police scanner, he scours the streets at night shooting content that eventually catches the attention of a local news station. The station hires the aspiring cameraman but is oblivious to how far he’s willing to go to make the front page.
Nightcrawler is a neo-noir and recent cult classic that serves as a reminder to audiences of Gyllenhaal’s incredible range and talent. The movie also stars Rene Russo and Bill Paxton and went on to earn an Oscar nomination for Best Original Screenplay.
Nightcrawler
Release Date October 31, 2014
Director Dan Gilroy
Cast Jake Gyllenhaal , Michael Papajohn , Marco Rodríguez , Bill Paxton , James Huang , Kent Shocknek , Rene Russo
Runtime 117 minutes
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