Jake Gyllenhaal is a versatile actor who has juggled between film and stage (having appeared on New York stages recently in “Sunday in the Park with George” as well as the play “Sea Wall”/”A Life”). He continues to choose roles that are challenging and unexpected.
Gyllenhaal has been nominated for an Academy Award for his performance in Ang Lee‘s “Brokeback Mountain,” as well as two SAG Awards for that performance including Best Supporting Actor. He was also nominated for two Golden Globe Awards (for 2010’s “Love and Other Drugs” and 2014’s “Nightcrawler”). Gyllenhaal was also nominated for a third Screen Actors Guild Award for his performance in “Nightcrawler.”
Currently, Gyllenhaal has a host of films on tap for release in 2020 and beyond. But until then, let’s raise a glass to the great performer by ranking his 17 best feature film appearances. Our photo gallery includes “Zodiac,” “Prisoners,” “Donnie Darko” and more.
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17. STRONGER (2017)
Image Credit: Lionsgate/Roadside Attractions Director: David Gordon Green; Writer: John Pollono. Starring Jake Gyllenhaal, Tatiana Maslany, Miranda Richardson.
This inspirational story is based on the real events surrounding the 2013 Boston marathon bombing. Gyllenhaal plays Jeff Bauman, based on his book of the same name. He is an ordinary man in Boston who became a symbol of hope after losing both legs in the tragedy. Gyllenhaal wisely never portrays Bauman as a victim but instead as a fighter, and Maslany (“Orphan Black”) as Jeff’s ex-girlfriend provides solid support.
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16. OCTOBER SKY (1999)
Image Credit: Deana Newcomb/Universal/REX/Shutterstock Director: Joe Johnston. Writer: Lewis Colick. Starring Jake Gyllenhaal, Chris Cooper, Laura Dern.
Joe Johnston’s biographical drama of the life of Homer Hickam was the first film to really put Gyllenhaal on the map. He plays Homer, a young man in a small West Virginia town in 1957 who is expected to follow his father’s path of being a coal miner, but instead, inspired by the launch of Russian satellite Sputnik 1, Homer decides that he wants to be a rocket engineer himself. Aided by several other classmates, Homer considers himself a “rocket boy” (of which the film’s title “October Sky” is an anagram) and manages several successful rocket launches before the group is falsely accused of starting a forest fire. Gyllenhaal, who was only 17 during filming, received terrific reviews upon the film’s release, as did the film, which, to borrow a rocket term, served as the launching pad to Gyllenhaal’s career.
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15. SPIDER-MAN: FAR FROM HOME (2019)
Image Credit: J Maidment/Columbia/Marvel/Kobal/Shutterstock Director: Jon Watts. Writers: Chris McKenna, Erik Sommers. Starring Tom Holland, Zendaya, Samuel L. Jackson, Cobie Smulders, Jon Favreau.
Gyllenhaal dipped his toe into the superhero universe in this latest Spider-Man film in which he plays Quentin Beck, a former Stark Industries employee who in his down time is the superhero Mysterio. His allegiances, however, are subject to question as to whether he is a good guy or a bad guy. When confronted by Peter Parker/Spider-Man (Tom Holland), he reveals his true stripes, but Gyllenhaal’s Mysterio remains a fascinating character and an interesting addition to the Marvel Comics Universe.
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14. WILDLIFE (2018)
Image Credit: IFC Films Director: Paul Dano. Writers: Paul Dano, Zoe Kazan. Starring Carey Mulligan, Jake Gyllenhaal, Ed Oxenbould, Bill Camp.
In Paul Dano’s underappreciated directorial debut, Gyllenhaal plays Jerry Brinson, a golf pro at a Montana country club who becomes fascinated by the firefighters taking on blazes in the nearby forests. He takes a low-paying job fighting those fires, which forces him to leave his wife Jeannette (Carey Mulligan) and son Joe (Ed Oxenbould) behind. Jeannette, resentful, embarks on an affair with older man Warren Miller (Bill Camp) who both fills the loneliness in her heart and may provide the family with a little extra income. When Jerry returns home and discovers his wife’s affair, he is utterly devastated. While Jerry is not the most upright of characters, Gyllenhaal’s performance as Jerry gives us an insight as to why he does what he does.
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13. THE GOOD GIRL (2002)
Image Credit: Dale Robinette/Fox Searchlight/REX/Shutterstock Director: Miguel Arteta. Writer: Mike White. Starring Jennifer Aniston, Jake Gyllenhaal, John C. Reilly.
Working alongside performers of the caliber of Jennifer Aniston and John C. Reilly seemed to prompt Gyllenhaal to step up his game in this tale of Justine, a small town Texas cashier (Aniston), who absolutely bored with her life with her husband (Reilly) suddenly sees a new young employee, Holden (Gyllenhaal) with whom she could possibly see a future, or at least an affair. Justine finds a kindred spirit with Holden, who took on his name thanks to his obsession with J.D. Salinger’s “The Catcher in the Rye” and its disillusioned lead character who feels some of the ennui that Justine now feels. Though “The Good Girl” is clearly Aniston’s movie, thanks to the quality of Mike White’s writing, Gyllenhaal’s Holden makes a huge impression, upping his reputation as a potential star.
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12. JARHEAD (2005)
Image Credit: Universal/REX/Shutterstock Director: Sam Mendes. Writer: William Broyles, Jr. Starring Jake Gyllenhaal, Jamie Foxx, Peter Sarsgaard, Chris Cooper.
“Jarhead,” the third film from Oscar-winning director Sam Mendes (“American Beauty,” “1917”), is based on Anthony Swofford’s best-selling remembrance of the first Gulf War. Rather than chronicling the thrill of battle, the film itself captures the ennui of not being allowed to fight, which is a frustrating situation for Swoff (Gyllenhaal). As a “jarhead” (slang for Marine), Swoff is trained as a sniper but by the time he is finally deployed to Iraq, the war is almost over, and his unit has to kill time waiting to be sent to a battle that will never come. Though the film received mixed reviews, Gyllenhaal’s depiction of a tightly-wound soldier constantly waiting to spring into battle received strong reviews and became another image gamble for Gyllenhaal that definitely paid off.
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11. THE SISTERS BROTHERS (2018)
Image Credit: Shanna Besson/Annapurna/Kobal/Shutterstock Director: Jacques Audiard. Writers: Jacques Audiard, Thomas Bidegain. Starring Joaquin Phoenix, John C. Reilly, Jake Gyllenhaal, Riz Ahmed.
In Gyllenhaal’s first Western (where he fits right in), the time is 1851 and Gyllenhaal plays John Morris, a private detective who is hired to track down a man named Hermann Kermit Warm (Riz Ahmed) who is also being pursued by notorious outlaws Eli (John C. Reilly) and Charlie Sisters (Joaquin Phoenix). Once he captures him, Morris becomes convinced that Warm is innocent and winds up partnering with him in his formula to find gold. It’s a wonderfully relaxed performance by Gyllenhaal, and his interactions with Ahmed are among the film’s highlights.
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10. ROAD HOUSE (2024)
Image Credit: Prime Video Director: Doug Liman. Writers: Anthony Bagarozzi, Charles Mondry. Starring Jake Gyllenhaal, Conor McGregor, Daniela Melchior, Billy Magnussen, Jessica Williams, Joaquim de Almeida.
There was no crying need to remake Patrick Swayze’s 1989 punchfest “Road House,” but if you’re going to take it on, you might as well have some fun with it. And that’s exactly what Gyllenhaal does in this reboot as his ex-UFC fighter Elwood Dalton takes a job as a bouncer at a rowdy Key West bar where he inevitably runs afoul of the criminal powers-that-be. It’s all absolute nonsense of course, but with his ripped body, droll delivery and impressive fighting skills, Gyllenhaal looks to be having the time of his life in the role, and that sense of fun is infectious.
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9. ENEMY (2013)
Image Credit: Roxbury Pictures/REX/Shutterstock Director: Denis Villeneuve. Writer: Javier Gullon. Starring Jake Gyllenhaal, Melanie Laurent, Sarah Gadon, Isabella Rossellini.
Gyllenhaal continued his successful artistic partnership with director Denis Villeneuve in this psychological thriller based on Jose Saramago’s novel “The Double.” Gyllenhaal conquers the challenge of playing two identical but very different men who come into one another’s lives. Adam (Gyllenhaal), a lonely academic, rents a film and spies an actor, Anthony Claire (also Gyllenhaal) who looks exactly like him. Intrigued that he has found his doppelgänger, Adam begins to stalk Anthony whose sexual nature turns out to be nothing like Adam’s. The two men begin to blend into each other’s lives until the film’s final shot, which is one of the most shocking that I have ever seen. With “Enemy,” Gyllenhaal set himself for an acting challenge which he conquered masterfully.
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8. NOCTURNAL ANIMALS (2016)
Image Credit: Courtesy of Focus Features Writer/Director: Tom Ford. Starring Jake Gyllenhaal, Amy Adams, Michael Shannon, Aaron Taylor-Johnson.
For this surreal thriller, Gyllenhaal plays the dual role of Tony Hastings and Edward Sheffield. Edward is an author who gives his ex-wife his latest novel to read, and she realizes that the characters could be actually based on them. She imagines the main character of Tony, a man whose family is brutally murdered in Texas, as being her ex-husband. Gyllenhaal received a BAFTA nomination for his performance.
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7. OKJA (2017)
Image Credit: Jae Hyuk Lee/Netflix/Kobal/Shutterstock Director: Bong Joon-ho. Writers: Bong Joon-ho, Jon Ronson. Starring Ahn Seo-hyun, Tilda Swinton, Jake Gyllenhaal, Paul Dano, Steven Yuen, Giancarlo Esposito.
Gyllenhaal gives perhaps what is his nuttiest performance in Bong Joon-ho’s Netflix film “Okja” as TV zoologist Dr. Johnny Wilcox who has an over-caffeinated television persona and who also works for the Mirando Corporation, a Monsanto-like company which is developing alternative food sources, such as breeding so-called “super pigs.” One of those 26 pigs is in South Korea being raised by a young girl named Mija (Ahn Seo-hyun) whose super pig Okja is really her best friend. As over-the-top as Gyllenhaal’s Dr. Johnny might be, it’s a pleasure to see this sometimes inwardly-focused actor let loose.
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6. END OF WATCH (2012)
Image Credit: Emmett/Furla Films/REX/Shutterstock Writer/Director: David Ayer. Starring Jake Gyllenhaal, Michael Peña, Anna Kendrick, America Ferrara.
Less a crime drama than a day-by-day look at the life of a pair of street cops, David Ayer’s “End of Watch” gave Gyllenhaal a new kind of acting challenge and he and co-star Michael Peña trained five months for their roles as police partners, including 12-hour ride-alongs with real cops and training in police tactics and weaponry. What came out of it was a thoroughly believable police team dealing with gang violence in South Central Los Angeles. Under the pretense of Gyllenhaal’s character shooting footage of the partners’ daily work life, Ayers gives “End of Watch” a documentary-like immediacy that gives both Gyllenhaal and Peña’s performances an extra layer of grit that neither actor had ever achieved before.
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5. DONNIE DARKO (2001)
Image Credit: Dale Robinette/Flower Films/Gaylord/Adam Fields Prod/REX/Shutterstock Writer/Director: Richard Kelly. Starring Jake Gyllenhaal, Jene Malone, Mary McDonnell, Patrick Swayze.
As the title character of this bizarre psychological drama, Gyllenhaal, who was only 20 at the time, took a huge risk in agreeing to take on the role, which, if it went wrong could have stopped the momentum of his growing career. However, even at that young age, Gyllenhaal showed the acting chops to handle the story of a disturbed young man who has visions of a figure dressed as a giant rabbit, who leads Donnie to commit destructive acts. Though Donnie is diagnosed as suffering from “paranoid schizophrenia,” no one steps in to stop Donnie, who claims that he is waiting for the imminent end of the world. As the film gained a following over the next few years, so did Gyllenhaal’s performance, and his high-wire act here led him to even greater roles to come.
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4. ZODIAC (2007)
Image Credit: Merrick Morton/Paramount/Warner Bros/REX/Shutterstock Director: David Fincher. Writer: James Vanderbilt. Starring Jake Gyllenhaal, Mark Ruffalo, Robert Downey Jr., Anthony Edwards.
David Fincher’s acclaimed retelling of the hunt to track down the feared Zodiac Killer who terrorized Northern California for nearly two decades, is led by Gyllenhaal in one of his most critically-admired performances. Gyllenhaal plays real-life political cartoonist Robert Graysmith of the San Francisco Chronicle who develops an interest in a local murder when the killer sends taunting notes to the newspaper. Graysmith’s theories on the killer’s identity are dismissed by the paper’s crime-beat reporters, but when his ideas begin to intrigue one of them (Robert Downey Jr.), he is brought onto the case. Graysmith plays to one of Gyllenhaal’s great strengths — the ability to appear to be naive, but when it comes down to it, he becomes tough and determined. And “Zodiac” is a perfect example of that.
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3. NIGHTCRAWLER (2014)
Image Credit: Bold Films/REX/Shutterstock Writer/Director: Dan Gilroy. Starring Jake Gyllenhaal, Rene Russo, Riz Ahmed, Bill Paxton.
In one of Gyllenhaal’s darkest but most acclaimed roles, he portrays Louis Bloom, a petty thief who comes upon a grisly accident and sees freelance journalists swarming around the violent aftermath. After learning that stringers, as they are called, earn considerable money selling their footage to local TV news shows, Lou obtains a camcorder and begins selling his footage to an L.A. local station, whose news producer Nina Romina (Rene Russo) is very much of the “if it bleeds, it leads” school. Soon Nina begins to rely on Lou’s footage for ratings, and Lou soon uses that reliance against her, threatening to withhold his footage unless they have sex. Gyllenhaal’s feral-like performance was rewarded with Best Actor nominations from both the Golden Globes and the Screen Actors Guild.
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2. PRISONERS (2013)
Image Credit: Moviestore/REX/Shutterstock Director: Denis Villeneuve. Writer: Aaron Guzikowski. Starring Hugh Jackman, Jake Gyllenhaal, Viola Davis, Maria Bello, Terrence Howard, Melissa Leo, Paul Dano.
Marking Gyllenhaal’s first collaboration with director Denis Villeneuve, “Prisoners” focuses on the Thanksgiving Day kidnapping of two little girls and how that act brings one of the parents involved (Hugh Jackman) to vengeance and the brink of madness. In what is arguably his best work as an investigative character, Gyllenhaal plays Detective Loki, who is brought into the case to find the kidnapper, which is difficult enough, but he must also contend with the crazed parent who seems determined to torture a confession out of the now-released initial suspect (Paul Dano), a young man with the IQ of a 10 year-old. Though playing the most grounded character in the film, Gyllenhaal shines in the film, bringing much welcome Pennsylvania color to what could have been a standard detective role.
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1. BROKEBACK MOUNTAIN (2005)
Image Credit: Focus Features/REX/Shutterstock Director: Ang Lee. Writers: Larry McMurtry & Diana Ossana. Starring Heath Ledger, Jake Gyllenhaal, Anne Hathaway, Michelle Williams.
In what is unquestionably Gyllenhaal’s most famous film role, he plays Jack Twist, who is hired to wrangle sheep on Wyoming’s Brokeback Mountain in 1963. Jack is sexually drawn to colleague Ennis del Mar (Heath Ledger), at whom Jack finally makes a pass, which leads to a long-term sexual and emotional relationship, even though both men eventually marry women. The sensitive performances delivered by both men garnered widespread acclaim, leading to Gyllenhaal’s first nomination for an Oscar, Golden Globe and Screen Actors Guild Award for Best Supporting Actor. (He was also nominated at SAG as part of the “Brokeback” ensemble cast.) If there was any doubt before, after “Brokeback Mountain,” Gyllenhaal had become not only a star, but an esteemed actor as well.
