Jake Gyllenhaal’s career spans over two decades, and the actor possess a wide variety of movies in his catalog. From obscure indie films to Oscar winners to Blockbusters and everything in between, Jake Gyllenhaal has done it all, creating a filmography that provides fans with an abundance of options. So for Jake Gyllenhaal fans or those looking to brush up on the actor’s best films, here is the list of must-watch Gyllenhall movies and where to stream them in alphabetical order.
Brokeback Mountain
Brokeback Mountain stars Gyllenhaal opposite Heath Ledger in a romantic Western directed by Ang Lee. It is one of Gyllenhaal’s most critically applauded films, and his performance alongside Ledger as Jack Twist is one of his best roles. The film won Ang Lee the Oscar for Best Director and Best Adapted Screenplay. Brokeback Mountain remains an influential LGBT film and gave Gyllenhaal one of his defining roles as a performer.
Brokeback Mountain is available to stream on Hulu, Sling TV, FuboTV, Amazon Prime and Showtime or to rent on YouTube, Google Play, Apple TV and Vudu.
Donnie Darko
Donnie Darko is a certified cult classic and one of Gyllenhaal’s most iconic films. It follows a teen who starts to see visions of someone in a rabbit costume named Frank after a weird accident. Frank informs him that the world will end in 28 days. The film is psychological and philosophical and has had fans pondering its true meaning for 20 years. Donnie Darko transcends its genre, creating something that continues to persist in some form with everyone who watches it and remains the film that catapulted Gyllenhaal’s career forward.
Donnie Darko is available to stream on Amazon Prime, Pluto TV and Tubi or to rent on Apple TV and Vudu.
Enemy
Enemy is a psychological thriller that features Gyllenhaal as two physically identical men with different personalities. Denis Villeneuve, director of Sicario, Blade Runner 2049 and the upcoming adaption of Dune, directs this doppelgänger thriller with his distinct visual style. Gyllenhaal is working with Villeneuve for the second time, creating a genuinely unique, tense and upsetting psychological thriller. As such, Enemy is an excellent example of the wide range of movies Gyllenhaal has been involved in throughout his career.
Enemy is available to stream on Hulu or to rent on Vudu and Amazon Prime.
Nightcrawler
Nightcrawler delivers a creepy and enthralling performance from Gyllenhaal. The neo-nori thriller comes right after Enemy and serves as another unsettling role for Gyllenhaal. Nightcrawler follows an eccentric freelance photographer/reporter who records and photographs violent crimes throughout the night in Los Angeles. To be the first individual at the scene of these violent crimes and accidents, Louis Bloom continually pushes the limits of the law and morality as he finds more success. Gyllenhaal falls into the character of Louis Bloom, giving off the sociopathic energy necessary for the part and elevating the film into must-watch territory as far as Gylennhall movies go.
Nightcrawler is available to stream on Netflix or to rent on Vudu, Amazon and Apple TV.
October Sky
October Sky is the first film to really showcase Jake Gylennahall and put his talents on the map. After appearing in other small movies and roles as a child actor, October Sky is Gyllenhaal’s coming out party. The film is based on a true story about a coal mining father whose son doesn’t want to follow in his footsteps and wants to study rocket science instead. October Sky is a solid family drama and essential for those wishing to see Gylennhaal’s beginnings as a star.
October Sky is available to stream on Peacock or to rent on Vudu, Amazon and Apply TV.
Okja
Directed by visionary filmmaker Bong Joon-Ho, Okja follows a young girl who takes care of a giant pig named Okja. The film is one of 2017’s best and tackles important issues like animal rights and the pitfalls of capitalism. For Gyllenhaal, it’s one of his zaniest performances. He plays an over-the-top TV zoologist who works for the big bad multinational corporation in the movie. Okja is a unique film, and Gyllenhaal really lets loose with his portrayal of Dr. Johnny Wilcox.
Okja is available to stream on Netflix.
Prisoners
Prisoners is the first collaboration between Gyllenhaal and Denis Villeneuve. The film focuses on the kidnapping of two young girls on Thanksgiving. Gyllenhaal plays detective Loki, who is tasked with solving the crime and dealing with a parent driven to the point of madness by the disappearance of his child. Gyllenhaal is the calm in the middle of Prisoners‘ storm, making it one of his most striking performances.
Prisoners is available to stream on Hulu or to rent on Vudu, Amazon and Apple TV.
Spider-Man: Far From Home
Gyllenhaal makes his Marvel Cinematic Universe debut in Spider-Man: Far from Home, playing one of the more fascinating antagonists in the MCU. Quentin Beck masquerades as a hero from the future called Mysterio, recruiting and misleading Spider-Man to help him get revenge against his former employer Tony Stark. Beck is, at times, seemingly sympathetic and a great mentor to Peter Parker. However, his character is at his best when his true nature is revealed, allowing Gyllenhaal to let loose and be the maniacal villain he was meant to be.
Spider-Man: Far From Home is available to stream on Starz, Amazon Prime and Philo or to rent on Vudu and YouTube TV.
Zodiac
Zodiac is David Fincher’s exploration of the hunt for the Zodiac Killer, the infamous serial killer who operated in northern California in the 1960s and 1970s. Gyllenhaal plays real-life cartoonist Robert Graysmith, who develops a theory about the killer that is promptly shot down until he starts to work with Paul Avery (Robert Downey Jr.), a reporter at the San Francisco Chronicle. Gyllenhaal gives one of his best performances, playing the determined but naive Graysmith. His chemistry with Robert Downey Jr. and how they juxtapose each other elevates his performance even more.
Zodiac is available to stream on Amazon Prime and YouTube or to rent on Google Play, Vudu and Apple TV.
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