An arguably underrated and multi-talented force in the film industry, Jake Gyllenhaal has been gracing our screens for just over 30 years now. As with many others in the industry, it helps to know somebody or be a bit more attractive than others to get where you want to go, and he has both. Father was a director and Mother was a producer/screenwriter, which helps a lot, but Jake has successfully taken that stepping stone and created his own next steps to stardom. Accepting vastly differing roles over the many years of his career, he has starred in some of the more shocking dramas of the new age of cinema. That wasn’t always a reach for him though, in one of his earliest films, Donnie Darko, Gyllenhaal got a chance to stretch his legs in a new genre and he hasn’t looked back since.
Outside of his film career, it is little known that Jake is also a practicing Buddhist, a giver to the community, and has a side-passion for cooking. Plus, he’s just a lovable guy to see in interviews and interacting with co-stars. He has a great — though competitive — relationship with his older sister Maggie, who is a very successful screen — and stage — actor in her own right. Jake is a treasure in all respects, which is why we are here to talk about the 10 of the best roles he has portrayed, starting from number 10.
10. The Day After Tomorrow (2004)
Starting off with a movie theater, surround sound, popcorn flick, The Day After Tomorrow is a cinematic reminder of what we are doing to our planet. Jake Gyllenhaal plays Sam Hall, son to paleoclimatologist Jack Hall (Dennis Quaid), who has just informed the U.N. about an imminent disaster. As Washington D.C. goes through an intensified Ice Age, Sam (Jake) is trapped in one of the many buildings fostering the lost and stranded. Jake’s character is a young student who is even smarter than his teachers, but who is now forced to show what he’s got against natural forces beyond what is thought possible. Jake portrays this well, genuinely expressing his fear and desperation as any would in such a situation. Plus, he’s got a crush on his classmate, Laura (Emmy Rossum), and who wouldn’t? Getting in his Jake Galahad moments is pivotal to the plot and his romantic desires, making this a good choice for the top 10.
Director: Roland Emmerich
Main Cast: Dennis Quaid, Jake Gyllenhaal, Emmy Rossum
Runtime: 124 minutes
IMDb Rating: 6.4
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9. October Sky (1999)
In Gyllenhaal’s first big role, October Sky is a heartfelt, family drama about a boy and his dreams. Gyllenhaal plays Homer Hickam, a young scientist who witnesses the first Sputnik launch in 1957, inspiring him to study rockets and how they fly. Considering this is a true story, it makes the Hollywoodized version fun and entertaining to behold. Playing his unapproving, coal mining father is Chris Cooper, who was born to spout the line “I’m disappointed in you” to any co-star playing his offspring. With a successful southern twang in his speech, Jake impressed audiences and critics alike enough to remember his name. This is not said to discredit his overall performance, which was more than enough to garner respect and attention as an up-and-coming on-screen talent.
Director: Joe Johnston
Main Cast: Jake Gyllenhaal, Chris Cooper, Laura Dern
Runtime: 108 minutes
IMDb Rating: 7.8
8. End of Watch (2012)
In this fast-paced action thriller, End of Watch seems to be just another cop flick but brings more to the table. Jake plays Officer Brian Taylor opposite Officer Mike Zavala (Michael Peña), two friends and young L.A. cops who stumble upon an unfortunate bust. Filmed in a documentary/handheld tracking shot style, this film is intense and emotional when it needs to be. When they confiscate money and guns from what they discover is the cartel, a price goes out on their heads that is broadcast to all the crime rings of L.A. to hear. In what is now an oversaturated movie sub-genre, this film does well to bring originality and sincerity thanks to the performances from Jake and Michael. Jumping from friendly banter to all-out action, this film has some tonal inconsistencies for sure but doesn’t take away from the impressive and emotional scenes that are its highlights.
Director: David Ayer
Main Cast: Jake Gyllenhaal, Michael Peña, Anna Kendrick
Runtime: 109 minutes
IMDb Rating: 7.6
7. Spider-Man: Far From Home (2019)
The second and last of the light-hearted and fun films on our list today, Spider-Man: Far From Home is a continuation of the Marvel universe where one would never expect to see our beloved star. Gyllenhaal is Mysterio, the tricksy illusionist opposite Spider-Man who — if you haven’t read any of the comics — turns out to not be such a great guy. With a backstory slightly altered to fit into the new MCU, Mysterio aka Quentin Beck is determined to trick the world into thinking he is the new great superhero, no matter how many human lives it costs. This film is unique in our list today, as it not only portrays Gyllenhaal as a villain but does so in an eccentric and comedic fashion. This role for Jake was not greatly accepted by all viewers (some die-hard Marvel fans and some who just love to hate) but given his past dramatic acting, this role was a fun and fresh view of Gyllenhaal that we had never seen before.
Director: Jon Watts
Main Cast: Tom Holland, Samuel L. Jackson, Jake Gyllenhaal
Runtime: 129 minutes
IMDb Rating: 7.5
6. Prisoners (2013)
The first of the truly emotional and intense films on our list today, Prisoners is a slow-burning mystery thriller that aptly depicts multiple viewpoints affected by child abduction. Gyllenhaal is Detective Loki, the man tasked with finding two young girls who have mysteriously and suddenly gone missing. Under immense pressure from Keller Dover (Hugh Jackman), the father of one of those girls, Loki does all that he can do to solve this dark labyrinth of a case that is seemingly unsolvable. Both Jackman and Gyllenhaal provide incredible performances in this film, showing what a person has the potential to become when he is faced with absolute inhumanity and darkness. Jake, nearly outshined by his co-star, holds his own and shows us that there is no such thing as a small role when it comes to acting.
Director: Denis Villenueve
Main Cast: Hugh Jackman, Jake Gyllenhaal, Viola Davis
Runtime: 153 minutes
IMDb Rating: 8.1
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5. Nocturnal Animals (2016)
An overall shocking and tragic film, Nocturnal Animals is a thriller that will stay with you forever. With an overall plot that is meant to make the viewer think, it’s not a film to watch while you do your sudoku. While we’re at it, you might want to watch this one by yourself. Jake plays Edward Sheffield, a successful author who sends his ex-wife Susan Morrow (Amy Adams) a morbid and violent novel of his. Interpreted as a revenge piece, Susan is haunted by the tale and how he used to call her a “Nocturnal Animal” due to her insomnia. Gyllenhaal also plays Tony Hastings, who is the lead character of the bleak novel Edward has written as Susan interprets it. While these two stories are occurring simultaneously, Tony goes through a horrific event on some desert backroads, ultimately leading to the gruesome loss of his current-day wife and teenage daughter. Playing two separate roles, Jake does a fantastic job as an accomplished author with an internal struggle, and a man at the end of his psychological rope. Before you watch this film, I can’t stress enough: It will stay with you forever.
Director: Tom Ford
Main Cast: Amy Adams, Jake Gyllenhaal, Michael Shannon
Runtime: 116 minutes
IMDb Rating: 7.5
4. Zodiac (2007)
In what is praised as one of the most historically accurate films to date, Zodiac takes the 70s cultural phenomenon and turns it into cinema gold. Robert Graysmith (Gyllenhaal) is a true crime author who was obsessed with solving the Zodiac case for over 10 years of his life, despite being a little-known newspaper cartoonist. Based off of Graysmith’s book of the same title, this film and all its accuracies actually caused the investigation to reopen. Being one of the best David Fincher films, this movie is dark and ominous all the way through, with Gyllenhaal being one of the main lights shining through the darkness–and Fincher’s first choice for the portrayal of Robert Graysmith thanks to his performance in Donnie Darko. Jake’s characterization in this film is much like the acclaimed author was in this time: obsessive and meticulous. Getting the details of the character right is so nuanced and masterful in the film, that even the slight stutters and nervous ticks are spot on. In an interview on the Today Show, Graysmith stated, “I didn’t know I was obsessed until this man {Gyllenhaal} portrayed me and I realized I was…in shock but he nailed it.”
Director: David Fincher
Main Cast: Jake Gyllenhaal, Robert Downey Jr., Mark Ruffalo
Runtime: 157 minutes
IMDb Rating: 7.7
3. Donnie Darko (2001)
In likely his most memorable role and a great film overall, Donnie Darko is, for many, who Jake will always be in our hearts. When the Darko family experiences a bizarre and nearly tragic incident, Donnie begins to see recurring visions of a man dressed in a very creepy rabbit costume. Troubled with mental health issues and curious sleepwalking journeys in the night, Donnie is coerced by the rabbit man to commit a series of vandalism-oriented crimes in their little, happy town. Struggling with multiple medications, troubles at home, and these dark thoughts, Jake takes the assignment and simply knocks this performance out of the park. As the film progresses, Donnie’s visions begin to frustrate him, making him slowly unravel and lash out against those closest to him. Besides his incredible performance, this film is one of the great mind-benders of the 20th century with people still talking about what it means and what actually happened. Another highlight of this film is that Maggie plays opposite Jake as his older sister, showing a bit of their competitive nature on the screen for all to see.
Director: Richard Kelly
Main Cast: Jake Gyllenhaal, Jena Malone, Mary McDonnell
Runtime: 113 minutes
IMDb Rating: 8.0
2. Brokeback Mountain (2005)
In his boldest and most adventurous role yet, Jake Gyllenhaal stunned audiences with his acting in Brokeback Mountain. A beautiful and saddening tale from visionary director Ang Lee, Gyllenhaal plays opposite Heath Ledger as two cowboys who build strong feelings for each other in a time and place where that could very well get you killed. After a summer in the mountains, they go back home to their separate lives and begin to build families with their girlfriends. This causes rifts in their relationships as they struggle to keep up the façade, longing to be with each other but conscious that it can never happen. Both stars of this film produce absolutely breathtaking performances, exploring the battle in oneself when coming to terms with one’s own sexuality. Gyllenhaal was so incredible and convincing in this role, that viewers and critics alike — doing what they do — began to speculate and rumor about the actor’s sexuality. Since we already know that is irrelevant to what we are talking about and none of our business, we will simply chalk it up to wonderful acting from Jake Gyllenhaal and move on.
Director: Ang Lee
Main Cast: Jake Gyllenhaal, Heath Ledger, Michelle Williams
Runtime: 134 minutes
IMDb Rating: 7.7
1. Nightcrawler (2014)
Provided with an exceptional screenplay from screenwriter/director Dan Gilroy, Gyllenhaal fully becomes the Nightcrawler. Gyllenhaal is Louis Bloom, a newcomer to the world of L.A. crime journalism who becomes obsessed with being the best. Driven to get the best shots and be the first one to do it, Bloom sacrifices his own health and humanity to cash in on one of the most controversial careers in this day and age. This film, while being a spectacular and original story, also goes to lengths to explore and question the morality and integrity of modern day journalism. As Bloom gets better and better at what he does, he not only stands idly by while violent crimes take place, he begins to manufacture them to make the scene look better — i.e. more tragic. While the character’s mental stability crumbles, Gyllenhaal puts forth his absolute best performance, shocking viewers with his range of emotion — and lack thereof. While this film is dark and haunting, it is certainly one of the best psychological thrillers of the decade that brings some important questions about our world to light. Luckily for those of us with a subscription, this is one the best movies on Netflix right now.
Director: Dan Gilroy
Main Cast: Jake Gyllenhaal, Rene Russo, Bill Paxton
Runtime: 117 minutes
IMDb Rating: 7.8
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