The 32 greatest Jake Gyllenhaal movies

EntertainmentMoviesThe 32 greatest Jake Gyllenhaal moviesWhen you purchase through links on our site, we may earn an affiliate commission.Here’s how it works. EntertainmentMoviesThe 32 greatest Jake Gyllenhaal moviesWhen you purchase through links on our site, we may earn an affiliate commission.Here’s how it works. When you purchase through links on our site, we may earn an affiliate commission.Here’s how it works. (Image credit: Summit Entertainment) 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) (Image credit: Walt Disney Pictures) 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) (Image credit: Universal Pictures) 30. Rendition (2007) (Image credit: New Line Cinema) 29. Moonlight Mile (2002) (Image credit: Buena Vista Pictures Distribution) Sign up for the Total Film Newsletter Bringing all the latest movie news, features, and reviews to your inbox 28. The Day After Tomorrow (2004) (Image credit: 20th Century Studios) 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) (Image credit: Miramax Films) 26. The Good Girl (2002) (Image credit: Fox Searchlight Pictures) 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. 25. Life (2017) (Image credit: Columbia Pictures) 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. 24. The Guilty (2021) (Image credit: Netflix) 23. Lovely & Amazing (2002) (Image credit: Lionsgate) 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) (Image credit: Amazon Studios) 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) (Image credit: Fox Searchlight Pictures) 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) (Image credit: Netflix) 19. Southpaw (2015) (Image credit: The Weinstein Company) 18. Spider-Man: Far From Home (2019) (Image credit: Sony Pictures Releasing) 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) (Image credit: Lionsgate) 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) (Image credit: Universal Pictures) 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) (Image credit: 20th Century Studios) 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) (Image credit: Universal Pictures) 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) (Image credit: Universal Pictures) 12. End of Watch (2012) (Image credit: Open Road Films) 11. Guy Ritchie’s The Covenant (2023) (Image credit: MGM) 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) (Image credit: Netflix) 9. Stronger (2017) (Image credit: Lionsgate) 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) (Image credit: Universal Pictures) 7. Source Code (2011) (Image credit: Summit Entertainment) 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. Source Code$5.94at Amazon$15.56at Amazon$17.19at Amazon Source Code $5.94at Amazon$15.56at Amazon$17.19at Amazon $5.94at Amazon $15.56at Amazon $17.19at Amazon 6. Brokeback Mountain (2005) (Image credit: Focus Features) 5. Wildlife (2018) (Image credit: IFC Films) 4. Prisoners (2013) (Image credit: Warner Bros.) 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) (Image credit: Newmarket Films) 2. Nightcrawler (2014) (Image credit: Open Road Films) 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. Nightcrawler7.8/10Watch at Netflix Nightcrawler 7.8/10 7.8/10 7.8/10 Watch at Netflix Watch at Netflix 1. 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This canceled Netflix fantasy series was one of the best shows of 2024 – and deserves a second chance Patton Oswalt and Jordan Blum explain why comics are still the perfect medium for superhero stories - “Visuals that will never be achieved in TV or movies can be achieved in comics” Team Asobi’s gigantic 2024 proves it’s time to free Astro Bot from PlayStation’s past Warhammer 40,000: Space Marine 2 was the favorite shooter of the year, and it also made me fall even harder for my fiancé 17 years on, Sam Barlow reflects on Silent Hill: Origins: “To pull it out of the bag with a seven-out-of-ten game was incredibly rewarding” Here’s our Black Ops 6 multiplayer playlist to keep you and your pals connected over Christmas Spy x Family season 3: Everything we know so far One of 2024’s best anime shows subverts all expectations, but that’s its biggest strength How Final Fantasy 7 Rebirth represents the best of Final Fantasy’s past while charting a course for the future GAME REVIEWSMOVIE REVIEWSTV REVIEWS1Nemesis review: “A magical sense of tension"2Arcs review: “A whole lot of game in a small package"3Path of Exile 2 review: “A stellar start to a thrilling and brutal dark adventure"4Indiana Jones and the Great Circle review: “The best adventure Indy has embarked on in over 30 years"5Marvel Rivals review: “So preoccupied with trying to be like Overwatch that it forgets to play to its own strengths"1Sonic the Hedgehog 3 review: “Keanu Reeves as Shadow is wasted whilst Jim Carrey steals the show"2Mufasa: The Lion King review – “It’s no Hakuna Matata but this Disney origin story is a class above the 2019 movie"3Kraven the Hunter review: “The insistence on an R-rating helps save this, with a decent helping of bloodthirsty action"4The Lord of the Rings: The War of the Rohirrim review – “An uninspired expansion of the most iconic screen take on Tolkien"5Nightbitch review: “Amy Adams' disappointing dark comedy is all bark and no bite"1Squid Game season 2 review: “Secures its place as one of the best shows on television right now"2Doctor Who 2024 Christmas special review: “Ncuti Gatwa is as magnetic as ever in this delightful festive treat"3Secret Level review: “An uneven experience with serious highlights that ultimately make up for the misses"4Skeleton Crew review: “Perfectly captures the vibes of classic Star Wars with a swashbuckling twist"5Creature Commandos review: “James Gunn’s heartwarming, R-rated tale about super-monsters proves that the DCU is in good hands” GAME REVIEWSMOVIE REVIEWSTV REVIEWS1Nemesis review: “A magical sense of tension"2Arcs review: “A whole lot of game in a small package"3Path of Exile 2 review: “A stellar start to a thrilling and brutal dark adventure"4Indiana Jones and the Great Circle review: “The best adventure Indy has embarked on in over 30 years"5Marvel Rivals review: “So preoccupied with trying to be like Overwatch that it forgets to play to its own strengths"1Sonic the Hedgehog 3 review: “Keanu Reeves as Shadow is wasted whilst Jim Carrey steals the show"2Mufasa: The Lion King review – “It’s no Hakuna Matata but this Disney origin story is a class above the 2019 movie"3Kraven the Hunter review: “The insistence on an R-rating helps save this, with a decent helping of bloodthirsty action"4The Lord of the Rings: The War of the Rohirrim review – “An uninspired expansion of the most iconic screen take on Tolkien"5Nightbitch review: “Amy Adams' disappointing dark comedy is all bark and no bite"1Squid Game season 2 review: “Secures its place as one of the best shows on television right now"2Doctor Who 2024 Christmas special review: “Ncuti Gatwa is as magnetic as ever in this delightful festive treat"3Secret Level review: “An uneven experience with serious highlights that ultimately make up for the misses"4Skeleton Crew review: “Perfectly captures the vibes of classic Star Wars with a swashbuckling twist"5Creature Commandos review: “James Gunn’s heartwarming, R-rated tale about super-monsters proves that the DCU is in good hands” GAME REVIEWSMOVIE REVIEWSTV REVIEWS1Nemesis review: “A magical sense of tension"2Arcs review: “A whole lot of game in a small package"3Path of Exile 2 review: “A stellar start to a thrilling and brutal dark adventure"4Indiana Jones and the Great Circle review: “The best adventure Indy has embarked on in over 30 years"5Marvel Rivals review: “So preoccupied with trying to be like Overwatch that it forgets to play to its own strengths"1Sonic the Hedgehog 3 review: “Keanu Reeves as Shadow is wasted whilst Jim Carrey steals the show"2Mufasa: The Lion King review – “It’s no Hakuna Matata but this Disney origin story is a class above the 2019 movie"3Kraven the Hunter review: “The insistence on an R-rating helps save this, with a decent helping of bloodthirsty action"4The Lord of the Rings: The War of the Rohirrim review – “An uninspired expansion of the most iconic screen take on Tolkien"5Nightbitch review: “Amy Adams' disappointing dark comedy is all bark and no bite"1Squid Game season 2 review: “Secures its place as one of the best shows on television right now"2Doctor Who 2024 Christmas special review: “Ncuti Gatwa is as magnetic as ever in this delightful festive treat"3Secret Level review: “An uneven experience with serious highlights that ultimately make up for the misses"4Skeleton Crew review: “Perfectly captures the vibes of classic Star Wars with a swashbuckling twist"5Creature Commandos review: “James Gunn’s heartwarming, R-rated tale about super-monsters proves that the DCU is in good hands” GAME REVIEWSMOVIE REVIEWSTV REVIEWS1Nemesis review: “A magical sense of tension"2Arcs review: “A whole lot of game in a small package"3Path of Exile 2 review: “A stellar start to a thrilling and brutal dark adventure"4Indiana Jones and the Great Circle review: “The best adventure Indy has embarked on in over 30 years"5Marvel Rivals review: “So preoccupied with trying to be like Overwatch that it forgets to play to its own strengths"1Sonic the Hedgehog 3 review: “Keanu Reeves as Shadow is wasted whilst Jim Carrey steals the show"2Mufasa: The Lion King review – “It’s no Hakuna Matata but this Disney origin story is a class above the 2019 movie"3Kraven the Hunter review: “The insistence on an R-rating helps save this, with a decent helping of bloodthirsty action"4The Lord of the Rings: The War of the Rohirrim review – “An uninspired expansion of the most iconic screen take on Tolkien"5Nightbitch review: “Amy Adams' disappointing dark comedy is all bark and no bite"1Squid Game season 2 review: “Secures its place as one of the best shows on television right now"2Doctor Who 2024 Christmas special review: “Ncuti Gatwa is as magnetic as ever in this delightful festive treat"3Secret Level review: “An uneven experience with serious highlights that ultimately make up for the misses"4Skeleton Crew review: “Perfectly captures the vibes of classic Star Wars with a swashbuckling twist"5Creature Commandos review: “James Gunn’s heartwarming, R-rated tale about super-monsters proves that the DCU is in good hands” GAME REVIEWSMOVIE REVIEWSTV REVIEWS 1Nemesis review: “A magical sense of tension” 1Nemesis review: “A magical sense of tension” 1 Nemesis review: “A magical sense of tension” 2Arcs review: “A whole lot of game in a small package” 2Arcs review: “A whole lot of game in a small package” 2 Arcs review: “A whole lot of game in a small package” 3Path of Exile 2 review: “A stellar start to a thrilling and brutal dark adventure” 3Path of Exile 2 review: “A stellar start to a thrilling and brutal dark adventure” 3 Path of Exile 2 review: “A stellar start to a thrilling and brutal dark adventure” 4Indiana Jones and the Great Circle review: “The best adventure Indy has embarked on in over 30 years” 4Indiana Jones and the Great Circle review: “The best adventure Indy has embarked on in over 30 years” 4 Indiana Jones and the Great Circle review: “The best adventure Indy has embarked on in over 30 years” 5Marvel Rivals review: “So preoccupied with trying to be like Overwatch that it forgets to play to its own strengths” 5Marvel Rivals review: “So preoccupied with trying to be like Overwatch that it forgets to play to its own strengths” 5 Marvel Rivals review: “So preoccupied with trying to be like Overwatch that it forgets to play to its own strengths” 1Sonic the Hedgehog 3 review: “Keanu Reeves as Shadow is wasted whilst Jim Carrey steals the show” 1Sonic the Hedgehog 3 review: “Keanu Reeves as Shadow is wasted whilst Jim Carrey steals the show” 1 Sonic the Hedgehog 3 review: “Keanu Reeves as Shadow is wasted whilst Jim Carrey steals the show” 2Mufasa: The Lion King review – “It’s no Hakuna Matata but this Disney origin story is a class above the 2019 movie” 2Mufasa: The Lion King review – “It’s no Hakuna Matata but this Disney origin story is a class above the 2019 movie” 2 Mufasa: The Lion King review – “It’s no Hakuna Matata but this Disney origin story is a class above the 2019 movie” 3Kraven the Hunter review: “The insistence on an R-rating helps save this, with a decent helping of bloodthirsty action” 3Kraven the Hunter review: “The insistence on an R-rating helps save this, with a decent helping of bloodthirsty action” 3 Kraven the Hunter review: “The insistence on an R-rating helps save this, with a decent helping of bloodthirsty action” 4The Lord of the Rings: The War of the Rohirrim review – “An uninspired expansion of the most iconic screen take on Tolkien” 4The Lord of the Rings: The War of the Rohirrim review – “An uninspired expansion of the most iconic screen take on Tolkien” 4 The Lord of the Rings: The War of the Rohirrim review – “An uninspired expansion of the most iconic screen take on Tolkien” 5Nightbitch review: “Amy Adams' disappointing dark comedy is all bark and no bite” 5Nightbitch review: “Amy Adams' disappointing dark comedy is all bark and no bite” 5 Nightbitch review: “Amy Adams' disappointing dark comedy is all bark and no bite” 1Squid Game season 2 review: “Secures its place as one of the best shows on television right now” 1Squid Game season 2 review: “Secures its place as one of the best shows on television right now” 1 Squid Game season 2 review: “Secures its place as one of the best shows on television right now” 2Doctor Who 2024 Christmas special review: “Ncuti Gatwa is as magnetic as ever in this delightful festive treat” 2Doctor Who 2024 Christmas special review: “Ncuti Gatwa is as magnetic as ever in this delightful festive treat” 2 Doctor Who 2024 Christmas special review: “Ncuti Gatwa is as magnetic as ever in this delightful festive treat” 3Secret Level review: “An uneven experience with serious highlights that ultimately make up for the misses” 3Secret Level review: “An uneven experience with serious highlights that ultimately make up for the misses” 3 Secret Level review: “An uneven experience with serious highlights that ultimately make up for the misses” 4Skeleton Crew review: “Perfectly captures the vibes of classic Star Wars with a swashbuckling twist” 4Skeleton Crew review: “Perfectly captures the vibes of classic Star Wars with a swashbuckling twist” 4 Skeleton Crew review: “Perfectly captures the vibes of classic Star Wars with a swashbuckling twist” 5Creature Commandos review: “James Gunn’s heartwarming, R-rated tale about super-monsters proves that the DCU is in good hands” 5Creature Commandos review: “James Gunn’s heartwarming, R-rated tale about super-monsters proves that the DCU is in good hands” 5 Creature Commandos review: “James Gunn’s heartwarming, R-rated tale about super-monsters proves that the DCU is in good hands”