10 Greatest Jake Gyllenhaal Movies, According to Letterboxd
Over the past two decades, few actors have displayed such a tremendous range of acting quite like Jake Gyllenhaal has. Beginning his acting career in 1991 with a supporting role in the comedy hit City Slickers, Gyllenhaal’s breakthrough came in 1999, when he portrayed a troubled teen who has visions of a world-ending event in Donnie Darko.
From there, he’s been cast in some highly acclaimed movies, ranging from a complex cowboy relationship in Brokeback Mountain, to helping catch a serial killer in Zodiac, Gyllenhaal has simply done it all. So, with the help of Letterboxd, let’s rank Gyllenhaal’s best movies, ranging from widely acclaimed to underrated masterpieces.
10
‘Southpaw’ (2015)
Letterboxd Rating: 3.6/5
After Rocky took audiences by storm in 1976, we’ve had a slew of boxing films that have ranged from great to so-so. Thankfully, Southpaw is in the former category. Here, Gyllenhaal stars as Billy “The Great” Hope, a reigning Light Heavyweight champion who’s seeking to get his life back on track after his wife was murdered, and his daughter was put in protective custody.
While the film received mixed reviews from critics, there was a broad consensus on the brilliant acting from Gyllenhaal, who played Billy with much conviction and emotion that, by this time, we’d come to expect from one of film’s best actors. Southpaw has become somewhat forgotten, which is a shame because it’s truly one of the most underrated boxing films you certainly have yet to check out.
9
‘Okja’ (2017)
Letterboxd Rating: 3.7/5
Only hardcore Gyllenhaal fans would know that he was part of a South Korean sci-fi film produced for Netflix. If you have yet to see Okja, then you’re missing out on a truly underrated performance by Gyllenhaal, who plays a disturbed zoologist and TV personality who is there to uncover the story of a genetically modified “super pig.”
Yes, the premise may seem a bit kitschy on the surface, but by the time you’ve reached the end credits of Okja, it will make you look at pork a lot differently. Also, you’ll be treated to a golden performance from Gyllenhaal, who really displayed his range as the TV personality trying to tell the story of this unique pig that’s being mistreated.
8
‘Nocturnal Animals’ (2016)
Letterboxd Rating: 3.7/5
As aforementioned in the intro, Gyllenhaal is a master at acting range, and in 2016’s Nocturnal Animals, that range was stretched even farther to give a truly unforgettable performance. Nocturnal Animals follows an art gallery owner (Amy Adams) as she begins to be consumed by the manuscript of a novel written by her ex-husband (Gyllenhaal), who dedicated the book to her.
Gyllenhaal and Adams had an electric chemistry between them, and you’ll get wrapped up in the tug-of-war that brews between her ex and her current, unfaithful husband (Armie Hammer). Nocturnal Animals was well-received by both critics and audiences, who especially heaped praise on the performances of Gyllenhaal and Adams. No wonder it’s a movie that Letterboxd users absolutely love.
7
‘October Sky’ (1999)
Letterboxd Rating: 3.7/5
Before breaking through with Donnie Darko (more on this later), Gyllenhaal was looking to cement his status as the next Hollywood star, and he took a huge step forward with October Sky. Directed by Joe Johnston, October Sky is based on the Homer H. Hickam Jr. memoir that tells the story of how he became a NASA engineer, being inspired by the launch of Sputnik 1 in 1957.
It’s certainly an honor to be rewarded with the lead role adapting someone’s memoir, and Gyllenhaal, who portrayed Hickam, played the role very well. While it was painful at times watching the father-son relationship play out, Gyllenhall, no doubt, brought his A-game to October Sky, and the end result is an underrated masterpiece that deserves a lot more love than it got.
6
‘End of Watch’ (2012)
Letterboxd Rating: 3.8/5
It’s tough being a cop in Los Angeles. Just check out the dozens of movies and TV shows that revolve around the challenging job LAPD officers have in keeping the City of Angels safe. One of those movies was 2012’s End of Watch, starring Gyllenhaal and Michael Peña as LAPD patrol officers who patrol one of the most dangerous beats in the city: South Central.
While most LA-centric cop movies and shows oftentimes glamorize how the LAPD takes down the bad guys, End of Watch was an especially gritty affair that looked at the less-glamorous day-to-day aspects of LAPD patrol work. The energy and grit Gyllenhaal and Peña brought to the film is palpable, and makes End of Watch both a satisfying and emotional watch.
5
‘Donnie Darko’ (2001)
Letterboxd Rating: 4.0/5
After 1999’s October Sky got Gyllenhaal off-and-running in Hollywood, his next feature film would prove to be his absolute breakout. That movie was 2001’s Donnie Darko, a surreal sci-fi psychological thriller that, to this very day, still gives me nightmares whenever I watch it. Gyllenhaal stars as the titular character, who survives an accident by sleepwalking, and, afterward, begins to see a bizarre figure dressed as a rabbit who tells him the world is coming to an end in a month.
Think about it for a second. What would you do if you saw a gnarly-looking rabbit in your dreams, proceed to tell you that you, and the rest of the world, are going to perish in a month? It’s something that Gyllenhaal’s character tries to figure out throughout the movie, and we were along for the trippy ride down the rabbit hole of conspiracy. Donnie Darko was a huge hit, and the movie that officially put Gyllenhaal on the path to stardom.
4
‘Zodiac’ (2007)
Letterboxd Rating: 4.0/5
If you’re a fan of mystery thrillers, then Zodiac is a movie that should be on your watchlist. Gyllenhaal was electric in this film, which tells the story of the hunt for the Zodiac Killer, a serial killer who gripped the San Francisco Bay Area in fear during the late-’60s and early-’70s. Gyllenhall portrays Robert Graysmith, a political cartoonist who begins to crack the code of the Zodiac Killer.
Gyllenhall’s performance was simply riveting, as he urgently tried to inform his colleagues that the Zodiac Killer’s messages were not as it seemed. Gyllenhaal, along with that of Mark Ruffalo as Inspector Dave Toschi, elevated the movie to classic status. Again, if you haven’t watched this film, I highly suggest you do. You’ll be on the edge of your seat like I was.
3
‘Nightcrawler’ (2014)
Letterboxd Rating: 4.0/5
If you thought that the performances that I already highlighted were not enough to convince you of Gyllenhaal’s tremendous range, then the next three movies on this list will most certainly will. Let’s start with Nightcrawler, the underrated 2014 neo-noir crime thriller that showcases Gyllenhaal at his most unhinged.
Here, he portrayed Louis “Lou” Bloom, a guy who’s down on his luck until he becomes a news stringer in Los Angeles. The role Gyllenhaal plays is one that will make your skin crawl. Although you’re sympathetic to Bloom at first, once he gets deep into his job, and starts making some truly questionable decisions, you’ll begin to look at him a lot differently, and not in a good way. That’s what I’m talking about when I say Gyllenhaal has tremendous range. One moment, he’s playing a son waiting to become a NASA engineer, the next, he’s creating crime scenes just to get that creepy money shot.
2
‘Brokeback Mountain’ (2005)
Letterboxd Rating: 4.1/5
It’s hard to describe how much of a cultural phenomenon Brokeback Mountain became when it was released in 2005. It was a highly controversial movie, as depicting same-sex couples on the big screen without it dissolving into a parody was rare back then. However, the story of two cowboys falling in love with each other and the ups-and-downs of their relationship was met with widespread acclaim.
It was also one of Gyllenhaal’s all-time best performances, with him and the late Heath Ledger giving a performance for the ages. Brokeback Mountain helped advance LGBTQ causes, and was preserved in the National Film Registry for its historical significance. While I would personally put Brokeback Mountain as Gyllenhaal’s best film, we’re going by Letterboxd, and, according to movie buffs, there’s another film that is considered his absolute best.
1
‘Prisoners’ (2013)
Letterboxd Rating: 4.3/5
In 2013, Denis Villeneuve tapped Gyllenhaal, Hugh Jackman, and Viola Davis in a movie that is considered by Letterboxd fans to be Gyllenhaal’s best movie. That film is Prisoners, a 2013 movie that tells the story of the abduction of two girls, and the desperate search to find them.
While Prisoners is technically a crime thriller, the movie has a lot of emotional movies that will hit home with any parent. Gyllenhaal plays the detective who’s trying to help find the missing girls, and his range as an actor is on full display here. He not only acts the part, he embodies the personality of the character he’s portraying, which he did to great acclaim with the portrayal of Detective Loki. While the movies on this list are some of his all-time best, it was Prisoners that fully cemented him as one of Hollywood’s most celebrated actors.
Prisoners
- Release Date
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September 20, 2013
- Runtime
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153 minutes
- Director
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Denis Villeneuve
- Writers
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Aaron Guzikowski
