The 32 greatest Jake Gyllenhaal movies
Oct. 25, 2024A friend is a gift you give yourself, and so is a good Jake Gyllenhaal flick
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The movies have always been in Jake Gyllenhaal’s blood. Born to a film director father and screenwriter mother, Jake Gyllenhaal has enjoyed a prolific and consistent career in Hollywood. But for all the years and movies he’s appeared in, which of them deserve the accolade as his greatest ever?
More specifically, Jake was born to film director Stephen Gyllenhaal and screenwriter Naomi Foner, and got his early start in movies playing Billy Crystal’s son in the 1991 hit City Slickers. But while Gyllenhaal enjoyed a handful of movie and TV roles in his teen years, his family insisted he work non-acting summer jobs to support himself, which led to jobs as a lifeguard and a restaurant busboy. While Gyllenhaal enrolled in Columbia University, he dropped out to pursue acting full time. In 1999, he landed his first leading role in a movie, which slowly but surely gave him the momentum for a career that’s never slowed down.
In celebration of his ongoing career, here are 32 of Jake Gyllenhaal’s greatest movies.
30. Rendition (2007)
The CIA’s ghoulish practices of extraordinary rendition is taken to task in Gavin Hood’s 2007 political thriller. Reese Witherspoon stars as the wife of an Egyptian-born engineer who is detained by American officials due to suspicions of having terrorist links. Gyllenhaal co-stars as Douglas Freeman, a CIA analyst who witnesses the engineer’s interrogation and harbors doubt about any involvement. As a politically minded film about America’s erosion of ethics in its post-9/11 hysteria, Rendition is kind of sloppy. But Gyllenhaal more than proves his leading man mettle.
Director and writer Brad Silberling takes inspiration from his own life in Moonlight Mile, a beautiful movie about love, loss, and learning to move on. Jake Gyllenhaal stars as Joe, a young man still mourning the death of his fiancé’s murder. Staying with his would-be in-laws (played by Dustin Hoffman and Susan Sarandon), Joe tries to move forward while grappling with the lingering emotional obligations he has to his fiance’s parents. In real life, Silberling lived such a story after his girlfriend – the actress Rebecca Schaeffer – was killed by a stalker in 1989.
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Gwyneth Paltrow wrestles with the burden of genius and inheritance in the moving drama Proof. Paltrow leads the movie as Catherine, the daughter of a celebrated mathematician (Anthony Hopkins) who suffered from severe mental illness before his death. Catherine’s father left behind a treasure trove in the form of hundreds of notebooks that chronicle his brilliance; among those after it is a former student (Jake Gyllenhaal), whose relationship with Catherine is complicated by his desire to dive into her father’s work. Gyllenhaal isn’t the center focus of Proof, but he is a wonderful scene partner for Paltrow in one of her most dramatic roles ever.
Jennifer Aniston undergoes an existential crisis in The Good Girl, with Jake Gyllenhaal providing a welcome releasevalvefrom an unremarkable marriage. The Friends star leads the movie as Justine, a retail store employee who begins a passionate extramarital affair with Holden (Gyllenhaal), a wry young coworker who aims for something more in life. While Justine enjoys the whirlwind of a fling, the harsh realities of life remain in place, and suddenly Holden’s dreams feel just like that: dreams. Gyllenhaal is quite funny in a part that is loosely an unofficial Holden Caulfield from The Catcher in the Rye.
It wasn’t the secret Venom prequel like some folks online thought it might be, but that doesn’t stop Life from being pretty fun. Jake Gyllenhaal stars with Rebecca Ferguson, Ryan Reynolds, and Hiroyuki Sanada as astronauts aboard the International Space Station who discover the first evidence of life on Mars. The problem: The lifeform is very intelligent, andverydangerous. While Life is deeply derivative of other space horror classics like Alien, Gyllenhaal proves himself a strong leading actor yet again, plus it features Ryan Reynolds in a rare non-comedy role.
Jake Gyllenhaal finds “hope” in the ring in Antoine Fuqua’s hard-hitting drama Southpaw. He plays reigning boxing champ Billy Hope whose undefeated streak masks a severe degeneration of his health. After his wife (played by Rachel McAdams) dies from a gunshot wound, Billy’s life falls apart, and he fights from the bottom to regain custody of his young daughter and reclaim his place at the top of the boxing world. Southpaw follows the same playbook as other boxing dramas like Rocky, Raging Bull, and Creed, but Jake Gyllenhaal is a formidable contender against cinema’s other great pugilists.
With Tony Stark gone, another bearded genius stepped up to mentor Peter Parker – or so he made everyone believe. In Spider-Man: Far From Home, Jake Gyllenhaal dons the domed helmet of Mysterio, who in the comics was a master of illusions. In the MCU, Gyllenhaal’s version of Quentin Beck poses as a hero from another dimension to get close to young Spider-Man and steal away precious Stark Industries technology as revenge against the late Iron Man. While Far From Home has wound up a so-so movie in the MCU’s vast canon, Gyllenhaal’s masquerade and subsequent villainous “turn” is, to borrow an adjective from Spider-Man’s own comic books, “amazing.”
For once, director Guy Ritchie eases up on his smarmy characters and British sarcasm to explore genuine friendship and loyalty in dangerous territory. Jake Gyllenhaal stars as a U.S. Army Green Beret who covertly returns to Afghanistan to rescue the interpreter (Dar Salim) who first saved him. The Covenant is a moving and rousing action movie about the strength of bonds that transcend barriers. It is also proof that Guy Ritchie can exercise tonal restraint even when bullets go flying.
Bong Joon-ho’s multilingual adventure drama spans the United States and South Korea, following a brave girl (played by Ahn Seo-hyun) who attempts to rescue her beloved, oversized “super pig” after she is abducted by a greedy corporation in the meat industry. Jake Gyllenhaal has a very memorable role as Dr. Wilcox, an eccentric zoologist and TV personality with a habit of smiling through his teeth. He takes “Okja” away to the U.S. on behalf of the Miranda Corporation, which kicks off the movie’s plot. Gyllenhaal isn’t the star of Okja, per se, but he’s hard to take your eyes off of with his carnival barker aura and prodigious mustache.
Based on Homer Hickam’s 1998 memoir, October Sky chronicles Hickam’s childhood in which the launch of Sputnik 1 inspired him to become a NASA engineer. Pursuing this path came at the cost of his father’s dreams for him to become a coal miner. Beyond its impossibly perfect metaphor of a country evolving into modernity, the movie is simply masterfully directed by Joe Johnston who gives the material its gravity. A young Jake Gyllenhaal delivers a memorable early leading man performance as Homer Hickam. Annual festivals honoring October Sky and its real-life story are held every year in Tennessee (which served as the shooting location for the movie) and in Coalwood, West Virginia, where Hickam actually grew up.
From director Duncan Jones, Jake Gyllenhaal stars in this clever science fiction thriller anchored around a loop of eight minutes on a Chicago commuter train. Gyllenhaal plays a U.S. Army pilot who is sent into a virtual reality simulation that recreates, with lifelike fidelity, a train explosion that took place earlier that morning. Gyllenhaal’s mission is to identify the terrorists who planted the bomb before another attack strikes. Complicating his goal is that Gyllenhaal’s character falls for a beautiful passenger (Michelle Monaghan) and desperately races to prevent her fate. A smarter and sharper sci-fi than meets the eye, Source Code – a slick mixture of The Matrix and Groundhog Day – hacks its way to the top thanks to a compelling Gyllenhaal.
One of Jake Gyllenhaal’s most impactful movies of his career, the actor co-stars with Carey Mulligan in this quietly incendiary family drama. Set in 1960 Montana, Gyllenhaal plays a family man who has lost a sense of purpose after he’s fired from his job at a country club. Drawn in by nearby forest fires, Gyllenhaal’s Jerry Brinson leaves his wife (Mulligan) and son (Ed Oxenbould) behind to support themselves. Wildlife is all about the complexities of family dynamics, manhood, and identity, all wrapped up in a disillusioned Americana.
Jake Gyllenhaal’s name of “Detective Loki” in Denis Villeneuve’s Prisoners is apt, given his chaotic search for the truth. In Villeneuve’s cerebral thriller, Gyllenhaal plays an obsessive detective who is determined to locate two missing girls. Things get difficult when one of the girls' father (Hugh Jackman) becomes increasingly unhinged and takes matters into his own hands, which forces Detective Loki on a race against time. Brimming with tension, Prisoners is a bleak movie that showcases Villeneuve’s filmmaking craftsmanship without the elements of science fiction he would soon be known for, through films like Arrival and the Dune movies.
Suburban teenage angst mixes with superhero science fiction in Richard Kelly’s new millennium classic Donnie Darko. Jake Gyllenhaal plays the title role, that of a troubled and sleepless teenager haunted by eerie visions of a man in a bunny costume. (Gyllenhaal’s real-life sister, actress Maggie Gyllenhaal, co-stars as his onscreen sister too.) Donnie lives the next few weeks turning the lives of everyone around him upside down, all before something terrible happens on Halloween night. A cult classic that bombed at the box office, Donnie Darko found its dedicated audience when it hit DVD, and has remained a favorite ever since.
Jake Gyllenhaal has never been so capable and so terrifying all at once than in Nightcrawler. He leads this neo-noir thriller as Louis Bloom, a Los Angeles drifter with a silver tongue who finds his calling as a stringer – freelance videographers who sell footage of harrowing crime scenes to local news stations. In this striking portrait of American capitalism that transforms human misery and anguish into a bloodsport, Gyllenhaal mesmerizes as an antihero who wreaks as much havoc as the ones captured on his cameras.
The bloody wrath of the Zodiac Killer is captured in David Fincher’s mid-aughts masterpiece Zodiac, released in 2007. Jake Gyllenhaal leads the movie as Robert Graysmith, a cartoonist for the San Francisco Chronicle who finds ways to crack the encrypted letters written – or so they believe to be written – by the Zodiac Killer. While the true identity of the Zodiac Killer was never solved (the movie carefully puts forward a possible subject), Gyllenhaal anchors this impeccably made mystery that isn’t so much about finding the truth as it is about how dark and destructive the search for it can feel.
Eric Francisco is a freelance entertainment journalist and graduate of Rutgers University. If a movie or TV show has superheroes, spaceships, kung fu, or John Cena, he’s your guy to make sense of it. A former senior writer at Inverse, his byline has also appeared at Vulture, The Daily Beast, Observer, and The Mary Sue. You can find him screaming at Devils hockey games or dodging enemy fire in Call of Duty: Warzone.
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