Movies

The Best Jake Gyllenhaal Movies (and where to stream them)

Jake Gyllenhaal, the Oscar-less powerhouse actor, has turned it iconic performance after performance in some of the greatest movies of the century. Here’s where to watch them.

Jake Gyllenhaal is arguably one of the greatest actors of his generation making his Oscar-less status a bit confounding. Nonetheless, he’s turned in some of the best performances of the 21st century in some beloved films. Even better, he rarely repeats a performance, so every movie is different. Here are some of our favorite Jake Gyllenhaal movies and where to stream them.

Zodiac ♌️

▶ Streaming on Prime Video

Zodiac tells the very true and very terrifying story of the infamous “Zodiac Killer,” who terrorized the San Francisco bay area in the late 1960s and early 70s. The movie follows three men obsessed with figuring out who the killer is: political cartoonist Robert Graysmith (Jake Gyllenhaal), journalist Paul Avery (Robert Downey Jr.), and detective Dave Toschi (Mark Ruffalo). Here’s the trailer.

Jake Gyllenhaal in Zodiac. Courtesy of Paramount Pictures.

Why it’s great: I often cite Zodiac as my favorite David Fincher movie — although if you ask me any other day that might change. It’s a dark and menacing crime thriller on its surface like Se7en, mixed in with an investigative drama. But Fincher is doing a lot more when you dig deeper. It’s a disorienting story. He plays with time and place to confuse you and put you in the headspace of the characters. Those characters are complex and motivated to a fault — Gyllenhaal’s Graysmith is borderline obsessive. You realize then that this isn’t a police procedural. You’re not watching to solve the mystery — you’re watching to solve the characters. 162 mins.


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Enemy ?

▶︎ Streaming on Hulu

Enemy follows Adam Bell (Gyllenhaal) is a college professor living an unremarkable life. That is until he watches a movie and discovers one of the actors (also Gyllenhaal) looks exactly like him. He becomes obsessed with learning the identity of his doppelgänger, but what he finds is even crazier than he — and us — could imagine. Here’s the trailer.

Jake Gyllenhaal and Jake Gyllenhaal in Enemy. Courtesy of Hulu.

Why it’s great: Enemy is a puzzle that needs — and wants — to be solved. However, director Denis Villeneuve and screenwriter Javier Gullón don’t make it easy for you, which makes the movie so fun to watch over and over again. They’re careful to give you clues and hints — some obvious and some you have to work for — that will guide you to some conclusion. But the real joy of the movie is that everyone’s conclusion will be different. Gyllenhaal gives two of his best performances as very distinct characters that share some bond. Look out for the small inflections he uses to differentiate the two. It’s masterful. 90 mins.

Nightcrawler ?

▶ Streaming on Netflix

Nightcrawler is about perpetual hustler Lou Bloom (Gyllenhaal) and his endless pursuit for success. One night, after witnessing stringers—freelance video journalists—recording footage from a car accident he finds his new line of work. As he dives deeper into the L.A. underbelly of crime, he maybe becomes too involved in getting the story. Here’s the trailer.

Jake Gyllenhaal in Nightcrawler. Courtesy of Netflix.

Why it’s great: Nightcrawler takes clear inspiration from two of my favorite Martin Scorcese movies — The King of Comedy and Taxi Driver — but it’s careful to emulate and not imitate. Instead, Lou Bloom is a wholly original and terrifyingly compelling anti-hero. His extreme obsession with his new career is offset by the fact that he’s actually good at it—for all the wrong reasons. As he defies any moral standard to get his story, we watch almost helplessly as people around him become pawns in his game rather than actual humans. And while a lesser movie would mine that for pure horror, Nightcrawler asks whether or not that’s already happening anyway in our society.


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Okja ♌️

▶ Streaming on Netflix

In Okja, set in the not too distant future, The Mirando Corporation led by CEO Lucy Mirando (Tilda Swinton) announces that they’ve bred a new species that they’re dubbing a “super pig.” They send the pigs out to 26 different farmers to find the best way to raise them. One of those farmers is Mija’s (Ahn Seo-hyun) grandfather. The young girl forges a bond with their super pig who they name Okja. So, when the Mirando Corporation and their hired animal “expert” Johnny Wilcox (Jake Gyllenhaal) take Okja away, Mija goes on a globe-trotting adventure to save her friend. Here’s the trailer.

Why it’s great: To try and classify Okja would be a disservice to the movie. It’s as one of a kind of a film as they come — and that’s its greatest virtue. For this movie to work, it has to march to the beat of its own drum. That beat is a wonderfully unconventional movie that’s sometimes satire, sometimes dark comedy, but all heart. And like any great Bong Joon-ho movie — and there are a lot of them — the biggest success is its characters. From Tilda Swinton’s wonderfully camp Lucy Mirando to Paul Dano’s cool and calm animal right activist Jay to Ahn Seo-hyun’s quiet but tough Mija to Okja herself, just like the movie’s style they’re wonderfully off-kilter and colorful, making them a delight to watch. 120 mins.


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Hey! I’m Karl. You can find me on Twitter here. I’m also a Tomatometer-approved critic.

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Karl Delossantos

Hey, I'm Karl, founder and film critic at Smash Cut. I started Smash Cut in 2014 to share my love of movies and give a perspective I haven't yet seen represented. I'm also an editor at The New York Times, a Rotten Tomatoes-approved critic, and a member of the Online Film Critics Society.

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