Jake Gyllenhaal has been wowing audiences with his big-screen performances for decades. The son of director Stephen Gyllenhaal and screenwriter and director Naomi Foner, Jake got his first taste of Hollywood when he was just 11 with a small part in Cityslickers, and over 30 years on, his filmography is packed full of great hits.
Considering he’s shown such a wide range in the projects he’s taken on, it’s a little difficult to rank Jake Gyllenhaal films. After all, can you really compare the big laughs and bigger action sequences in Spider-Man: Far From Home to the unbearable tension of Nightcrawler or the beautiful emotional journey of Brokeback Mountain? Even though it might be a bit of a fool’s errand, we’ve decided to give it a go.
So, whether you’re a Gyllenhaal stan who wants a list on the internet to be mad at, or you’re dipping your toe into the world of Maggie Gyllenhaal’s brother and want to know where to begin, read ahead for the 10 best Jake Gyllenhaal movies, ranked.
10. Okja
We kick off the list with this Korean-American critical hit. Veering between humorous and heart-wrenching, Okja is a charming yet gripping allegory about animal mistreatment under capitalism and the mass meat industry. The film follows one of 26 “super pigs” that were sent out to farms all over the world by the evil Mirando Corporation under the guise of “environmental research.” A decade on, one of them, the massive Okja, is living happily in South Korea with a young girl named Mija and her family until Mirando kidnaps the animal. We follow Mija as she battles against cruel and powerful meat industry interests to get her pig back, helped by animal rights activists and a few others as she does so.
Gyllenhaal plays Johnny, a neurotic, loud, and obnoxious TV personality and zoologist. He really goes for it in a manner that can seem over the top, but in the context of the film it works well. Okja itself is a vital meditation on what we eat, and how utterly destructive and evil the meat industry — driven by a psychotic need for profit at all other costs — can really be.
9. Zodiac
The 2007 David Fincher mystery thriller Zodiac captivated audiences with its slow burn and intensity. The film follows writers at the San Francisco Chronicle and detectives in the San Francisco police force as they chase the infamous Zodiac killer, who terrorized the public in northern California in the late sixties.
Gyllenhaal stars as Robert Graysmith, a political cartoonist who eventually became heavily involved in the Zodiac Killer case thanks to his ability to decrypt the puzzles that the serial killer left for police and the public. Graysmith eventually wrote a book about the murders, but not before his marriage crumbled thanks to his obsession with the deaths. The film itself was widely praised for its depictions of the psychological stress of chasing a serial killer, but its incredibly long run time and lack of real action bumps it down the list.
8. Spider-Man: Far From Home
As the final film in Phase 3 of the MCU, expectations around Spider-Man: Far From Home were through the roof for many fans of the franchise. Thankfully, the 2019 film delivered a great story, plenty of emotion, and a lot of laughs along the way. The plot follows Peter Parker (Tom Holland) as he teams up with and then battles Quentin Beck/Mysterio (Gyllenhaal) across Europe, giving us some great action scenes in iconic locations. And, of course, there’s a bit of romance between Parker and MJ (Zendaya).
Gyllenhaal really took to the role of Mysterio, diving deep into the character when working on the film, and was praised for his performance. The movie is generally considered one of the best in the MCU, thanks to the way it tied together many loose ends from Endgame.
7. October Sky
This emotionally wrought biographical drama about a miner’s son with his head in the stars is one of Gyllenhaal’s first true hits. The film is based on the memoir Rocket Boys by Homer Hickam, and follows a young Homer’s life as he moves from the mines of West Virginia into the world of rockets. Aside from a slightly weird bit where they praise Nazi rocket engineer Wenher von Braun (who was brought over to the U.S. as part of Operation Paperclip, something that’s had absolutely no negative effects on America’s culture or attitudes towards white supremacy) the film hits the right notes, with poignant moments and real, likable characters.
Gyllenhaal played Hickam incredibly well, bringing real depth and emotion to the role. October Sky was also praised heavily for its values and portrayal of Homer’s father John (Chris Cooper) as a layered, albeit tough, character.
6. Source Code
The compelling sci-fi thriller Source Code captivates as much as it will have you clenching the edge of your seat in suspense. The film follows an army vet as he uses a machine called the “source code” to enter a simulation of the last 8 minutes before a terrorist attack on a commuter train so that he can find the bomber and prevent future attacks. However, as the story unravels, the audience learns there’s much more to the “source code” than it being a simple simulation.
Gyllenhaal is excellent as the lead in this highly-rated sci-fi film. Humanity resides at the heart of all the action, which is what drives it from an interesting premise into a movie that’s well worth a watch.
5. Stronger
Brutal in parts yet ultimately a recovery story that transcends cliché, Stronger tells us the real-life story of a victim of the Boston bombing as he recovers and battles PTSD from the event. The film is buoyed by excellent performances and delves into the nuances of a man damaged not only by a terrorist attack but his own family’s history and his inability to commit to relationships.
Stronger is a great watch as it throws us right into the nitty-gritty of recovery, and although it ultimately ends on a high note, the film isn’t evangelical about the power of time and love to heal all wounds, instead striking more of a realistic tone. Gyllenhaal is excellent as the lead and even earned himself a Hollywood Film Award for his performance.
4. Donnie Darko
Creepy bunnies, multiple timelines, and a horrific plane crash: cult classic Donnie Darko is a daring must-watch that showcases Gyllenhaal’s incredible range (and also gives us the chance to see him act alongside his sister Maggie). The strange, unnerving film is part sci-fi, part horror, and part coming-of-age story, all held together by a number of tremendous performances, not least of all Jake Gyllenhall as the titular Donnie.
Full of menace and tension, and punctuated by odd humor and jump scares, Donnie Darko is often seen as one of the best indie films of its time. Although it didn’t do so well at the box office (the film’s plot includes a plane crash, so advertising was very limited post-9/11), it’s definitely entered the pantheon of hits, earning rave reviews from audiences and critics alike.
3. Wildlife
An emotional tour de force, Wildlife expertly toes the line between drama and sentiment, giving us a heartbreaking portrayal of a family on the verge of disintegration. Based on a 1990 novel of the same name by writer Richard Ford, Wildlife covers a lot of hard ground while maintaining sympathy for its characters and keeping the audience engaged.
The three lead actors (Gyllenhaal, Carey Mulligan, and Ed Oxenbould) all earned rave reviews for their performances, which elevated the story into a gripping tale about how people grow apart. An accomplished, fine film, Wildfire packs a lot into its 104 minutes and is well worth the watch.
2. Nightcrawler
Creepy, intense, and immensely watchable, Nightcrawler is without a doubt one of Gyllenhaal’s finest performances. The film shows the story of Lou, a thief turned photographer who races to accidents and crimes across L.A. to snap gruesome shots to sell to papers and television stations. The already dark movie unravels into black as the plot moves along, and we see an increasingly desperate and unhinged Lou angling for the most titillating pictures.
Gyllenhaal’s performance as the charming, sociopathic Lou earned him several rave reviews and award nominations, including for a Golden Globe. Nightcrawler was also consistently on top-ten lists of the year and continues to be a favorite of cinephiles today.
1. Brokeback Mountain
Could number one on this list have been anything else? The Academy Award-nominated film based on the short story of the same name by Annie Proulx follows the tale of two tough cowboys who begin an intimate relationship while ranching in the wilds, and shows us how their love seeps down into every facet of their lives.
Brokeback Mountain’s success is widely seen as a watershed moment for queer cinema, and the performances by the two leads (Gyllenhaal and Heath Ledger) were incredible, earning Gyllenhaal an Oscar nomination. If you put this film on you’ll have your eyes glued to the screen, you’ll cry, and you’ll be watching something that notorious moron and shill Rush Limbaugh hated – so positives all round!
