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.
32. Prince of Persia: The Sands of Time (2010)
For a while it was the greatest movie based on a video game, if only because it was halfway watchable. Based on the video game franchise (and titled after the 2003 hit installment), Jake Gyllenhaal stars as a street urchin turned rogue prince who teams up with a princess (Gemma Arterton) from a rival kingdom to safeguard a mystical dagger that can control time. The Prince of Persia: The Sands of Time is a big and noisy VFX spectacle, and Gyllenhaal's attempt at a Middle Eastern accent is kind of hilarious. But there's a charm to the movie that feels reminiscent of classic swashbucklers and sword-and-sandal fantasies like The 7th Voyage of Sinbad, Conan the Barbarian, and The Mummy.
31. Everest (2015)
Jake Gyllenhaal reaches the mountain peak in Everest, a 2015 survival thriller from Icelandic director Baltasar Kormákur and based on the 1996 Mount Everest disaster – still one of the deadliest expeditions ever taken on the fabled mountain. Gyllenhaal stars as real-life mountaineer Scott Fischer, whose years of experience are challenged when a blizzard strikes and his group is left in danger. Everest may not tread unexplored territory, but its stunning cinematography, emotional storytelling, and a strong leading performance by Gyllenhaal, make it a journey worth undertaking.
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.
29. Moonlight Mile (2002)
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.
28. The Day After Tomorrow (2004)
Roland Emmerich maintained his status as the premier disaster auteur with 2004's The Day After Tomorrow, an ensemble blockbuster that includes Jake Gyllenhaal. He plays the son of a climatologist (Dennis Quaid) who is trapped in a suddenly frozen New York City amid an apocalyptic climate event. The Day After Tomorrow is classic Hollywood disaster spectacle mixed with then-groundbreaking visual effects, but an up-and-coming Jake Gyllenhaal is no special effect as the movie's grounded everyman perspective.
27. Proof (2005)
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.
26. The Good Girl (2002)
Jennifer Aniston undergoes an existential crisis in The Good Girl, with Jake Gyllenhaal providing a welcome release valve from 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.
25. Life (2017)
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, and very dangerous. 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.
24. The Guilty (2021)
In 2021's The Guilty Jake Gyllenhaal parks behind the desk at a 911 call center and takes audiences on a wild ride all while sitting in a single location. The actor plays a police officer on probation who is stuck working the night shift as an emergency operator, but things take a sharp turn when Gyllenhaal's character receives an urgent distress call from a mother who has been kidnapped by an unknown party. A bottle thriller where the action takes place in real time, The Guilty is a must-see cinematic exercise, though it pales in comparison to Gustav Möller's original Danish-language thriller upon which it's based.
23. Lovely & Amazing (2002)
Jake Gyllenhaal enjoys a supporting role in Nicole Holofcenter's delicate comedy-drama Lovely & Amazing, which premiered at Telluride in 2001. Gyllenhaal plays a sensitive but confident underage teenager who enters a fling with Michelle (Catherine Keener), an unhappily married woman. While the movie pulls no punches over how wrong and icky their relationship is, Gyllenhaal and Keener's performance instill a strange sense of positivity between two people who know what they want and what they need. There's nothing wrong, except for everything.
22. Road House (2024)
It may not stack up to the original Road House with Patrick Swayze, but Jake Gyllenhaal is quite the heavyweight in Doug Liman's 2024 remake. Gyllenhaal stars as a former UFC fighter attempting to overcome his bloodlust when he takes a job bouncing at a rowdy bar in the Florida Keys. Soon, Gyllenhaal goes toe-to-toe and fist-to-fist with a gang mercenary (Conor McGregor). Although Gyllenhaal's Dalton tries to put his violent past behind him, he reluctantly uses his skills to save the only place he has left.
21. Demolition (2016)
The last film from Jean-Marc Vallée before his death in 2021, Jake Gyllenhaal stars in Demolition as a man in mourning who forges a deep connection with a very attentive customer service representative. He plays a wealthy banker still reeling from the death of his wife in a car accident. A negative experience with a hospital vending machine leads him to contact the manufacturer, his personal letters resonating with troubled company rep Karen (Naomi Watts). Over time, the two find themselves changing each other's lives forever. Demolition isn't terribly inventive, but sympathetic performances from its leads – Gyllenhaal's especially - make it a moving experience for anyone who feels like they just need to be heard.
20. Velvet Buzzsaw (2019)
Jake Gyllenhaal finds out how much criticism can really hurt in the black comedy thriller Velvet Buzzsaw, released on Netflix in 2019 and written/directed by Dan Gilroy. He stars as Morf Vandewalt, a snooty art critic who finds himself caught in a deadly mystery after a deceased artist's paintings amass acclaim. A pulpy parable about the perversion of art as a commerce, Velvet Buzzsaw doesn't land all the shots it takes, but it's delectable and intriguing, even if it doesn't match up to Gilory and Gyllenhaal's previous collaboration in Nightcrawler.
19. Southpaw (2015)
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.
18. Spider-Man: Far From Home (2019)
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."
17. Brothers (2009)
At last, someone in Hollywood took advantage of how much Jake Gyllenhaal and Tobey Maguire look like siblings. In Jim Sheridan's Brothers (a remake of a 2004 Danish film), Maguire plays a U.S. Marine who returns from Afghanistan with severe PTSD. Returning home, he finds that his younger brother (Gyllenhaal) has become very close to his wife (Natalie Portman) and his children in his absence. Brothers is a movie about the limits of brotherly bonds and the destructive power of paranoia that eerily echoed American psychology amid the devastating War on Terror.
16. Jarhead (2005)
In the thick of America's War on Terror in the Middle East, movies like Jarhead gave audiences a glimpse at new angles of modern warfare. Although Sam Mendes' film had a somewhat misleading promotion as a rousing military action movie in the spirit of Black Hawk Down, Jarhead instead reveals the surprising war waged among soldiers abroad: against boredom and a lack of purpose. Gyllenhaal plays real-life U.S. Marine Anthony Swofford, in an adaptation of his 2003 memoir that chronicles his service in the Gulf War.
15. Love & Other Drugs (2010)
For Jake Gyllenhaal, love is intoxicating in the 2010 rom-com Love & Other Drugs. Based on the 2005 nonfiction book Hard Sell: The Evolution of a Viagra Salesman – which chronicles the rise of Viagra in the marketplace from the perspective of one of its earliest salesmen – Gyllenhaal plays an aimless womanizer who gets into the pharmaceutical sales business and stumbles into being one of the first to sell Viagra in the late 1990s. Through it all, Gyllenhaal's Jamie Randall falls in love with a captivating young woman (Anne Hathaway) with early onset Parkinson's disease. While Love & Other Drugs could and maybe should have been a movie about the popular drug's impact on the world, it is still a lovely and funny romance about finding purpose and happiness in unlikely places.
14. Ambulance (2022)
Michael Bay returns to form in 2022's Ambulance, a rip-roaring action movie centered around a hijacked, runaway ambulance. Jake Gyllenhaal stars as a veteran criminal who ropes his adoptive brother and former soldier (Yahya Abdul-Mateen II) into a bank heist to pay off urgent bills. The brunt of the movie's action sees the brothers take control of an ambulance with an EMT (Eiza González) and a severely wounded police officer (Jackson White). For anyone nostalgic for the Michael Bay of yore who gave them flicks like The Rock and Bad Boys, Ambulance feels like an overdue emergency rescue.
13. Nocturnal Animals (2016)
Jake Gyllenhaal puts on a sleepless performance in his dual roles as Edward and Tony in Tom Ford's searing cerebral thriller Nocturnal Animals. In the movie's main narrative, Susan (Amy Adams) is a wealthy art gallery owner who receives an advance copy of a novel manuscript written by her ex-husband Edward (Gyllenhaal). The movie weaves in and out of Edward's story – a pitch black revenge tale about family man Tony (also Gyllenhaal) who seeks to kill the sadistic gang leader (Aaron Taylor-Johnson) that assaulted and murdered his wife and daughter. As dark and raw as Edward's novel is, it doesn't compare to the psychological torture that Susan suffers in the real world from seeing Edward's lingering resentment. Even if it's just words on a page, words still cut deep.
12. End of Watch (2012)
Writer/director David Ayer brings audiences into the grind of police work in his gritty action-thriller End of Watch, released in 2012. Jake Gyllenhaal and Michael Peña co-star as Los Angeles cops who embark on their jobs patrolling crime-ridden South Central L.A.. The movie takes the point of view of a handheld digital camera owned by Gyllenhaal's Taylor. At a time when the vérité style was typically found in supernatural horror, Ayer's End of Watch showcased the style being applied to heighten the tension and immersion into a more realistic subject matter.
11. Guy Ritchie's The Covenant (2023)
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.
10. Okja (2017)
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.
9. Stronger (2017)
In addition to the cruel loss of life, the Boston Marathon bombings of 2013 claimed the legs of runner Jeff Bauman, a Boston native who survived the explosion and wrote about his recovery in the memoir Stronger in 2014. In 2017, director David Gordon Green helmed a sincere cinematic adaptation of Bauman's book and experiences. A step above your run-of-the-mill inspirational drama, Jake Gyllenhaal gives a stirring performance as Bauman as he struggles in his thrust-upon image of a "hero" to the public while suffering from post-traumatic stress disorder.
8. October Sky (1999)
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.
7. Source Code (2011)
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.
6. Brokeback Mountain (2005)
"I wish I could quit you." While often the target of ridicule because of its sensitive subject matter, Brokeback Mountain is still a moving drama from director Ang Lee (who took home Best Director at the Academy Awards) and left a tremendous impact in ushering queer cinema into the mainstream. Jake Gyllenhaal and the late Heath Ledger play two Wyoming cowboys who fall in love over a 20-year period. All the while, the men hide their passion for each other from friends and family due to rampant homophobia. Brokeback Mountain won widespread acclaim from critics in 2005. In 2018, it was selected for preservation by the National Film Registry.
5. Wildlife (2018)
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.
4. Prisoners (2013)
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.
3. Donnie Darko (2001)
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.
2. Nightcrawler (2014)
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.
1. Zodiac (2007)
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.
