From a cowboy in 'Brokeback Mountain' to Donnie Darko himself, discover Jake Gyllenhaal's best movies, ranked by Metascore.
Jake Gyllenhaal is an American actor whose career ranges across genres, from romantic dramas to psychological thrillers. He is the son of director Stephen Gyllenhaal and screenwriter Naomi Foner, and his older sister is actor and director Maggie Gyllenhaal. Gyllenhaal began acting from a young age, making his acting debut in City Slickersat age 11. His breakthrough roles were as Homer Hickman in October Sky and as the titular Donnie Darko in the 2001 thriller.
Over the course of his career, Gyllenhaal has received much critical acclaim. For his role opposite Heath Ledger in Brokeback Mountain, he received the BAFTA Award for Best Actor in a Supporting Role and was nominated for the Academy Award for Best Supporting Actor. In 2010, he was nominated for Best Actor at the Golden Globe Awards for his performance as the lead in the romantic comedy-drama Love & Other Drugs. For his performance in the 2014 thriller Nightcrawler, Gyllenhaal was nominated by the Critics' Choice Awards, the Golden Globe Awards, and the Screen Actors Guild Awards in their Best Actor categories.
More recently, Gyllenhaal has appeared in the films Velvet Buzzsaw as art critic Mort Vandewalt, the Marvel sequel Spider-Man: Far From Home as the villain Mysterio, and The Guiltyas detective Joe Baylor. In 2019, Gyllenhaal appeared alongside Tom Sturridge in Sea Wall/A Life, a role for which he was awarded a Tony nomination for Best Actor in a Play.
As for future projects, Gyllenhaal is slated to appear in Michael Bay's Ambulance, Guy Ritchie's The Interpreter, Francis and the Godfather, Cut and Run, and a film adaptation of the musical Fun Home. He is also set to reprise the role of George in London's Savoy Theatre production of Sunday in the Park with George, a production which had been postponed due to the COVID-19 pandemic.
Here, Metacritic highlights the best movies Gyllenhaal has appeared in, ranked by Metascore.
Best for: Fans of Ang Lee and Western dramas
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Adapted from the 1997 short story by Annie Proulx and set in 1963 Wyoming, Brokeback Mountain follows the story of rodeo cowboy Jack Twist (Gyllenhaal) and ranch-hand Ennis Del Mar (Ledger). The two first meet when they are hired to herd sheep over the summer on Brokeback Mountain, during which they develop a physical and romantic relationship. Once the summer ends, Jack and Ennis part ways and proceed to live separate lives but continue to grapple with their feelings for one another, amounting to a love story of much deserved critical acclaim. In addition to its numerous nominations, Brokeback Mountain was awarded three Academy Awards for Best Director, Best Adapted Screenplay, and Original Score, as well as three BAFTA Awards for Best Film, Best Adapted Screenplay, and Best Performance by an Actor in a Supporting Role (for Gyllenhaal).
"The remarkable thing director Ang Lee has done is to have made a film that remains firmly in the Western genre while never retreating from its portrayal of a tragic love story." — Ken Tucker, Vulture
Best for: Fans of family dramas
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Set in the 1960s, Wildlife tells the story of the Brinsons, a family that has recently moved to Montana and struggles to make ends meet. When the father Jerry (Gyllenhaal) decides to work as a firefighter, he leaves his wife Jeanette (Carey Mulligan) and son Joe (Ed Oxenbould) but ends up being a head of household in a different way. Joe suddenly finds himself playing the role of an adult, left to support his mother and witness her struggles as she tries to keep their family afloat. The American drama film is notably Paul Dano's directorial debut and received critical acclaim for both direction and performances.
"Wildlife isn't just a great first film, it's a great film." — Lindsey Bahr, Associated Press
Best for: Fans of Westerns and assassins
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Based on the novel by Patrick deWitt, The Sisters Brothers, co-written and directed by Jacques Audiard, follows the tale of the infamous assassin brothers Eli (John C. Reilly) and Charlie Sisters (Joaquin Phoenix) as they chase after private detective John Morris (Gyllenhaal) and Hermann Warm (Riz Ahmed), who are in search of gold. In this hostile world, the two brothers are put to the test by the manhunt, their journey taking them from the Northwest to Oregon and eventually California, as they deal with elusive targets and employers more dangerous than they seem.
"Audiard has made an atmospheric Western in which the four lead actors portray their characters with remarkable subtlety." — Soren Andersen, The Seattle Times
Best for: Fans of David Fincher and mystery thrillers
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Inspired by true events, Zodiac chronicles the search for the Zodiac Killer, a San Francisco serial murderer of the late 1960s and early 1970s who was known to taunt law enforcement with ciphers, letters, and bloodstained clothing that were sent to newspapers. The case remains one of the most infamous unsolved crimes in the United States. The film follows political cartoonist Robert Graysmith (Gyllenhaal) who interprets the coded messages sent by the killer and begins to work alongside crime reporter Paul Avery (Robert Downey Jr.). As the investigation unfolds, Robert dives deeper and deeper into the mystery of the killer's identity and finds that he's losing himself along the way.
"Rarely has a film with so much blood on its hands seemed so insistently alive." — Manohla Dargis, The New York Times
Best for: Fans of psychological thrillers and crime reporting
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Nightcrawler follows petty thief Louis Bloom (Gyllenhaal) as he scavenges around Los Angeles to make ends meet. One night by chance, Louis discovers the market for cameramen, specifically those who capture the videos of crimes that are then distributed by news channels. With a camcorder and police scanner at his disposal, Louis ventures out into the city at night in search of its most shocking crimes. It is when news director Nina (Rene Russo) teams up with him in an effort to raise her ratings that Louis begins to push the limits of how far he's willing to go to get the shot.
"You'll have a closeup view of one of the movie year's most compelling sociopaths. He's something you can't turn away from." — Richard Corliss, Time
Best for: Fans of biographical dramas and rooting for the underdog
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Based on the memoir by the same name, Stronger tells the story of Jeff Bauman (Gyllenhaal), a Boston native who loses his legs in the Boston Marathon bombings and is left to pick up the pieces of his new life. At the marathon finish line to cheer on his ex-girlfriend Erin (Tatiana Maslany), Jeff finds himself right at the site of the bomb when it goes off. When he regains consciousness in the hospital, he remembers that he saw the bomber before the explosion and is able to assist local authorities who eventually capture them. Now praised as a hero, Jeff juggles the overwhelming nature of the press, the bad influences of his alcoholic mother, and his own indifference to his PTSD and physical recovery.
"There's a raw, tangible humanity to nearly every scene that sets the film gratifyingly apart." — Leah Greenblatt, Entertainment Weekly
Best for: Fans of female-driven narratives
Where to watch: iTunes
Runtime: 91 minutes
Lovely & Amazing tells the story of Jane Marks (Brenda Blethyn), her adult daughters Michelle (Catherine Keener) and Elizabeth (Emily Mortimer), and her Black adopted pre-teen daughter Annie (Raven Goodwin) as they each navigate their own world of insecurities. Jane struggles with her age and weight; Michelle, a struggling artist, finds herself falling for the attention of her teenage coworker Jordan (Gyllenhaal); Elizabeth, an aspiring actress, seeks reassurance when she is rejected for a role based on her appearance; and Annie struggles with feeling that she doesn't fit in with her white adopted family.
"Here is a movie that knows its women, listens to them, doesn't give them a pass, allows them to be real: It's a rebuke to the shallow 'Ya-Ya Sisterhood.'" — Roger Ebert, Chicago Sun Times
Best for: Fans of Bong Joon-ho and super pigs
Where to watch: Netflix
Runtime: 120 minutes
In 2017 in South Korea, a young girl named Mija (Seo-Hyeon Ahn) lives with her grandfather and their genetically modified super pig, Okja. Okja, one of the 26 specimens of the distributed super pig, is visited by zoologist Dr. Johnny Wilcox (Gyllenhaal) who deems Okja the best super pig of the specimens and declares that she must be sent to New York. Despite Mija's objections, Okja is sent to the United States, leaving the young protagonist no choice but to follow her pig to the States in order to save her from the mistreatment of the meat industry.
"Barbs of satire pop up and are washed away on streams of strong emotion. It's all marvelously preposterous and yet, at the same time, something important is at stake." — A.O. Scott, The New York Times
Best for: Fans of Inception, thrill seekers
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Source Code stars Gyllenhaal as U.S. Army Captain Colter Stevens who is sent on a mission to identify the terrorist who bombed a Metra train going into source Chicago. In order to do so, with the help of advanced technology, Stevens is sent into an eight-minute digital recreation of the real-life explosion and is given only the duration of those few minutes before the explosion to investigate. The mission is taxing, however, leaving Stevens often disoriented and skeptical of the mission at hand, bringing his very purpose and existence into question.
"Director Duncan Jones achieves a strange and winning amalgam, a gripping action film that also works as poetry." — Mick LaSalle, San Francisco Chronicle
Best for: Fans of psychological thrillers and Halloween season
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Set in October 1988, Donnie Darko follows Donnie (Gyllenhaal), a troubled teen who has a vision of a mysterious figure in a rabbit costume who tells him that the world will end in a little over 28 days. Donnie, an established sleepwalker, wakes up on a golf course and goes home to find that he narrowly escaped a tragic accident. As he continues to have visions of the mysterious figure, the world around him begins to unravel, leaving Donny to question the very constructs of life itself. This narrative is challenging and dark as Donny grapples with the realities of mental illness or perhaps the realities of a world about to end.
"Like gathering storm clouds, Donnie Darko creates an atmosphere of eerie calm and mounting menace — stands as one of the most exceptional movies of 2001." — Jean Oppenheimer, New Times (L.A.)
Best for: Fans of Jennifer Aniston and romantic dramedies
Where to watch: Not available via streaming
Runtime: 93 minutes
The Good Girl follows Justine Last (Aniston), a depressed 30-year-old who lives in a small town in Texas and works at the local retail store. Feeling unappreciated by her husband Phil (John C. Reilly) who usually smokes weed in his free time and feeling dissatisfied by her routine at work, Justine begins to get closer to her new coworker Holden (Gyllenhaal). As Justine lets go and challenges her status quo, she is forced to contend with the consequences of her actions, leaving her to question what she truly stands for.
"A sharp-tongued, subtly nuanced tragicomedy starring Jennifer Aniston, who shows her depth as a serious actress in this dark tale." — Claudia Puig, USA Today
Best for: Rocket scientists, fans of Laura Dern
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Based on a true story, October Sky tells the tale of Homer Hickam (Gyllenhaal), a high school student inspired by the launch of Sputnik 1 to pursue rocketry despite his father's wishes that he follow in his footsteps and become a coal miner. Set in 1957 in West Virginia, Homer begins building rockets with the help of his friends and teacher Miss Riley (Dern). Despite his father's attempts to discourage his interest, Homer proves himself in both spirit and science to be a rocket worth betting on as he dreams of a better life.
"Immensely entertaining and unabashedly inspirational." — Joe Leydon, Variety