10. Okja (2017)
Jake Gyllenhaal is known for playing serious and complex characters with his subtle sensibilities, which makes his role in Bong Joon-ho’s “Okja” all the more surprising. A fun and action-packed adventure yarn that follows a South Korean girl’s journey to save a “super pig” from the slaughterhouse.
Gyllenhaal appears as part of an ensemble cast (which includes Tilda Swinton and Paul Dano) as a wacky and buffoon of a TV personality/zoologist who’s sold his soul to the corporate world. Moving out of his comfort zone, Gyllenhaal chews the scenery and spits it out in a hilarious and creepy performance we’ve never seen him undertake before. Although the film and Gyllenhaal’s performance can be shaky at times, it’s still a charming romp that gives you something to think about. And we can’t help but hope we see him in more roles like this.
9. End of Watch (2014)
David Ayer’s “End of Watch” follows the day-to-day lives of two LAPD officers. While there’s a certain familiarity that runs through the film, Ayer’s honest script does away with unrealistic action and drama for a more honest portrayal of police work. It’s a buddy cop film that looks more at the friendship of its characters with a hit/miss found-footage style.
Gyllenhaal and Michael Peña are what make the film pop with their raw performances and natural chemistry. These are two police officers who spend their days responding to calls, talking and arguing on a range of topics, and spending time with their families. It’s a refreshing film and refreshing look at cops that mostly avoids the clichés and pratfalls of the genre.
8. Prisoners (2013)
The first of two collaborations Gyllenhaal had with Denis Villeneuve that year, “Prisoners” looks at the impact of a child abduction case on the multiple characters involved. Whether it’s the emotionally exposed father who takes things into his own hands after the police release the only suspect, or the police detective who feels the pressure as the window of solving the case starts closing, everyone involved is a prisoner of some kind.
Villeneuve makes the most with his first English-language film, with a powerhouse cast that also includes Hugh Jackman, Melissa Leo, Terrence Howard, Viola Davis and Paul Dano, with the legendary Roger Deakins providing some striking cinematography. Amidst the emotional performances, it’s Gyllenhaal’s subtle and multilayered turn that steals the show.
7. Source Code (2011)
Duncan Jones’ (“Groundhog Day”) science fiction thriller is a breath of fresh air that hits all the right notes. Gyllenhaal plays an Army captain who’s sent repeatedly back in time to find a train bomber during the last eight minutes of a schoolteacher’s life. Every time he’s sent back, he has to piece together clues and work against the clock to prevent a future attack.
“Source Code” is an exhilarating ride that never overstays its welcome. At brisk and tight 90 minutes, Jones keeps things going at a quick pace, never wasting a single moment. Gyllenhaal gives one of his most compelling and charming performances. His rapport with the underrated and brilliant Michelle Monaghan gives the film extra points alongside strong performances from Vera Farmiga and Jeffrey Wright.
6. Stronger (2017)
Based on the true story and memoir of Jeff Bauman who lost his legs in the Boston Marathon bombing, “Stronger” is a refreshing inspirational drama. Gyllenhaal gives another captivating performance as Bauman, who tries to pick up the pieces of his life after the tragedy, which includes becoming a hero and helping authorities find the bomber.
By sticking closely to the facts and underplaying the big emotional moments with realism, director David Gordon Green makes “Stronger” something special. The chemistry between Gyllenhaal and Tatiana Maslany, who plays Bauman’s girlfriend, is the kind of love story audiences can get behind because of its honesty. Along with his alcoholic mother, played by Miranda Richardson, Bauman is not your typical inspirational hero, but his charm gives what could’ve been an overly melodramatic biopic a sense of entertainment.
5. Enemy (2013)
With Denis Villeneuve’s “Enemy,” Gyllenhaal was able to cross off one item that’s on every actor’s bucket list: playing a dual role of two characters who look exactly the same but have contrasting personalities, but are linked somehow. And unsurprisingly he pulls it off effortlessly next to some controlled and precise direction from Villeneuve.
The first character is a meek college professor who lives a repetitive and unfulfilling life, who one day watches a film that appears to have his doppelgänger, a confident actor with a struggling career and pregnant wife. With a mindfuck storyline that makes you think for days after you finish watching it, the real entertainment comes from Gyllenhaal’s performance, which alone is worth the viewing.
4. Donnie Darko (2001)
Although a box office disappointment upon its release, this enduring cult classic is responsible for the increase of lead roles for the actor. Starting him on the course of playing likable but disturbed characters, Gyllenhaal stars as the titular hero who tries to find the meaning behind his trippy and cryptic doomsday visions.
Mixing science fiction, mystery, fantasy, a bitching soundtrack, and whatever else was in Richard Kelly’s head, “Donnie Darko” is one of the most unique and memorable films to come along in a long, long time, and the actor’s first masterpiece.
3. Brokeback Mountain (2005)
Ang Lee’s sweeping and majestic romantic western is notable for taking its complex and controversial story and ensuring there’s much more to it beyond the hype. The late Heath Ledger and Gyllenhaal play two cowboys who find themselves emotionally and sexually drawn to each other in a place and time that frowns upon such relationships.
Propelling its two main stars to greater superstardom and establishing them as ‘serious’ actors, “Brokeback Mountain” has Ledger and Gyllenhaal undertaking the bravest and most empathetic performances of their careers with the chemistry to match. Beyond the jokes and parodies, it’s a film that’s lost none of its potency and power over the years.
2. Zodiac (2007)
Procedurals like courtroom films can be hard to pull off, but with “Zodiac,” David Fincher not only perfected the genre but perfected his craft in what’s one of the best films of the 21st century. The film is based on the non-fiction book of the same name by Robert Graysmith that documented his investigation of the Zodiac Killer and his killing spree around San Francisco in the late 1960s and early 1970s.
Gyllenhaal plays the real-life Graysmith, who works as a political cartoonist at the newspaper company where the Zodiac Killer sends his encrypted letters. As the media frenzy follows the case, Graysmith becomes obsessed with finding the identity of the killer, clues which he’s convinced are right in front of them. Gyllenhaal holds his own alongside an amazing cast which includes Mark Ruffalo, Anthony Edwards, Brian Cox, and a scene-stealing Robert Downey Jr.
1. Nightcrawler (2014)
If you were to pick a signature film for each actor, one film that best shows their talents and what they can do, then there’s no doubt that “Nightcrawler” would be Jake Gyllenhaal’s signature film. Arguably, it has his best performance, and even more arguably, it’s his best overall film.
Following the rise and rise of a sociopath named Lou Bloom who finds his true calling as a stringer that records footage of violent crimes late at night throughout Los Angeles, then sells them to local news stations, it’s a dark twist on the usual success story with none of the clichés where the bad guy wins and the bad guy is the hero.
“Nightcrawler” has Gyllenhaal fully embracing the creepy and awkward side that’s appeared beneath some of his performances and characters before. From his weight loss, calm demeanor, well-spoken vocabulary, and bug eyes he made popular before “Mr. Robot” came along, the film features Gyllenhaal at his most mesmerizing. Add in Dan Gilroy’s smart script and stylish direction with veteran Robert Elswit behind the camera and the perfect supporting cast, and you have yourself a flawless film.