Since his deeply affecting breakout roles in early films like October Sky and Donnie Darko, Jake Gyllenhaal has proven to be one of his generation's most versatile leading men. As a creep, a romantic, or an action star, the actor always brings intensity and passion to his best projects. He's starred in some of the 21st century's strongest thrillers like Zodiac and Enemy, and has also created memorable characters in dramas, comedies, Westerns, and beyond.
Many of his roles feel incredibly natural, but Gyllenhaal also isn't afraid to take big, unusual swings with his style, as seen in the larger-than-life and off-the-wall energy of his later performances. From turns as a dedicated detective to a demented zoologist, here are the best performances of Jake Gyllenhaal's wide and varied acting career.
<i>October Sky</i> (1999)
A fresh-faced Gyllenhaal leads this wholesome period drama about West Virginia high schoolers who build rockets in their backyard after being inspired by Sputnik and the early space race. The actor displays earnest, starry-eyed wonder whenever he's talking about or working on his experiments, and manages to make dorky scientific processes seem genuinely entrancing.
By contrast, he carries himself with defeated dismay when his peers and mentors don't share his enthusiasm for engineering, and looks heartbroken and resigned whenever he tries to explore other career paths. It's an emotionally weighted breakthrough role for a then-17 year old Gyllenhaal, and one that proved his acting chops at his career's onset.
If you liked October Sky, you might also enjoy: Stand by Me (1986)
<i>Donnie Darko</i> (2001)
Cult classic Donnie Darko casts Gyllenhaal in the central role as a moody teenager in a medicated haze with "emotional problems." He sleepwalks, lashes out against his parents, and smokes with his friends, but his rebellion feels somewhat unnatural. Gyllenhaal makes the most of his character's surreal side, as he enters strange periods of near-hypnosis where he's totally detached from his surroundings, only to suddenly snap out of it. And though he does have revealing moments of sensitivity — he speaks kindly to strangers, chimes into classroom discussions with passion, and helps out people in need — it isn't enough to stop his spiral, taking the viewer (and a Virgil-like bunny named Frank) down with him.
If you liked Donnie Darko, you might also enjoy: The Virgin Suicides (1999)
<i>Lovely & Amazing</i> (2001)
Nicole Holofcener's dramedy Lovely & Amazing follows a family of women looking for reassurance and a sense of self-worth. Michelle, played by Catherine Keener, rebels against her passionless husband by flirting with her teenage co-worker, played by Gyllenhaal. The actor finds the perfect balance that the character deserves — he's charming enough that you understand why Michelle would risk it all for an underage affair, but young and innocent enough that their relationship still feels deeply uncomfortable. He's earnest, kind, and a little dumb, telling his rightfully skeptical mother that "Michelle is my lover." It's clear that he aspires to be taken seriously, but his natural naivety and puppy dog energy make it impossible unless he grows up a little more.
If you liked Lovely & Amazing, you might also enjoy: You Can Count on Me (2000)
<i>Brokeback Mountain</i> (2005)
Ang Lee's seminal neo-Western casts Gyllenhaal beside Heath Ledger as two rugged cowboys who share a passionate summer romance with lasting implications. Brokeback Mountain makes great use of Gyllenhaal's inherent romanticism, utilizing his loving gaze at every possible juncture as the outgoing Jack. His character starts as a light-hearted goof who sings at the top of his lungs and embraces his lover Ennis (a subduedLedger) without fear or self-consciousness. Later, his idealism gives way to pain when a full-blown relationship can't materialize, and the actor naturally breaks down into quiet, reluctant tears as a lover of life loses the love of his life. In his final scenes, Gyllenhaal embodies heartbreak, effortlessly conveying anger and disappointment at his partner, his own pain, and the world that wouldn't let them be together.
If you liked Brokeback Mountain, you might also enjoy: The Power of the Dog (2021)
David Fincher's fact-based crime thriller Zodiac is a fantastic display of everything that Gyllenhaal has to offer. Like most of the actor's early roles, Robert Graysmith starts the film as a gentle, soft-spoken character with a quiet but sweet disposition that radiates naivety. In a newsroom full of veteran San Francisco Chronicle journalists, Robert's being a cartoonist grants him an outsider status that implicitly makes you want to protect him, and his inquisitive demeanor around solving the Zodiac killer's cryptic codes is the stuff underdogs are made of.
As the film progresses, his curiosity snowballs into obsession, which means Robert transitions into the kind of character that Gyllenhaal gravitates toward later in his career — an intense, unstable oddball that inspires discomfort everywhere he goes. His wide-eyed gaze and rapid-fire line deliveries denote hyperfixation and paranoia, which makes sense given his proximity to a mysterious serial killer, but also alienates those around him as they work on the common goal of uncovering the murderer.
If you liked Zodiac, you might also enjoy: Se7en (1995)
In the psychological family melodrama Brothers, Gyllenhaal plays Tommy, an ex-con who takes care of his sister-in-law Grace (Natalie Portman) after his brother Sam (Tobey Maguire) goes missing in action in Afghanistan. Tommy starts the film as a washed-up, selfish jerk whose smug carelessness irritates everyone around him. But as he bonds with Grace, his rougher edges get sanded down, and Gyllenhaal sells his transition into a warmer, friendlier man who takes on difficult responsibilities. It's a rapid transformation, but the actor ensures that it feels natural and earned, and you root for him to win the film's complex relational battles by the time it concludes.
If you liked Brothers, you might also enjoy: Brothers (2004)
<i>End of Watch</i> (2012)
Gyllenhaal plays a charming young police officer in this crime drama directed by David Ayer. End of Watch rides on the actor's fraternal chemistry with his on-screen partner Michael Peña, and their camaraderie feels so natural that it often seems completely improvised. Their playful teasing makes way for genuine intimacy that's rare in American action movies, which subsequently makes it totally believable that they'd take bullets for each other.
Gyllenhaal also has strong romantic chemistry with Anna Kendrick — they flirt, embrace, and even perform an elaborately choreographed dance to Salt-N-Pepa's "Push It." The film's authenticity is also aided by the fact that his character is making a documentary film about police work, which means Gyllenhaal also doubles as a camera operator for many of the film's key scenes, requiring advanced coordination between his performance and his camerawork.
If you liked End of Watch, you might also enjoy: Training Day (2001)
Denis Villeneuve's other 2013 thriller Prisoners also stars Gyllenhaal, this time as Detective Loki, who is searching for an enraged and grief-stricken father's (Hugh Jackman) missing daughter. He starts out a little rough around the edges, eating alone in a restaurant on Thanksgiving, but he's clearly passionate about his job, and manages to stay calm and collected when talking down Jackman's character from his worse impulses (or at least trying to).
Loki's intense thirst for justice makes it unsurprising when we see him bend the rules to follow his instincts while pursuing suspects. Even as he's clearly overinvested in his work, Gyllenhaal brings a vigor to our would-be hero that helps him on the case — but at a certain unethical cost.
If you liked Prisoners, you might also enjoy: Gone Girl (2014)
Gyllenhaal crafts an impressive dual performance in Denis Villeneuve's psychological thriller Enemy. He plays two characters who look identical and covertly investigate their mysterious doppelgangers, and it's always remarkably clear which version of Gyllenhaal is on screen at any given moment. The primary character, Adam, speaks in a shakier but kinder tone and has a slightly deflated posture, whereas Anthony, an actor, carries himself with a much more confident, comfortable demeanor. Adam is defined by slight insecurity and gentleness, while Anthony maintains a harder-edged composure. Gyllenhaal never resorts to obvious tells or tics to differentiate the characters — their subtly distinct dispositions are more than enough to make the difference clear —and they're both fully realized roles in their own right.
If you liked Enemy, you might also enjoy: Memento (2000)
In this chilling thriller from Dan Gilroy, Gyllenhaal plays Lou Bloom, an aspiring freelance video journalist who's so driven to capture criminal activities on film that he starts implicating himself in crime scenes in dangerous ways. Nightcrawler's anti-hero is easily Gyllenhaal's most disturbing role to date, as he's a collection of behaviors that feel like an alien mimicking human patterns rather than an actual person. He's manic, manipulative, and willing to do anything to get a good story. There's a deadness behind his bulging eyes that totally lacks empathy, so it's unsurprising when he proves to be completely indifferent toward the people he offends and hurts — all for the chance of the money shot.
If you liked Nightcrawler, you might also enjoy: The King of Comedy (1982)
In boxing drama Southpaw, Gyllenhaal plays a rougher character than his usual type. He speaks aggressively in a lower register than he typically employs, and spends a lot of the movie covered in bruises. The actor got in impeccable shape to embody the character of Billy Hope, a champion boxer whose family has been torn apart, bringing a raw intensity to each of the film's fight sequences.
The tragic loss of his wife to an accident and his daughter to CPS fill him with rage and remorse, and he lets it all out in the ring with magnetic intensity radiating off his performance. Gyllenhaal also manages to pivot to a paternal softness in scenes with his character's daughter while still maintaining the always-present undertones of aggression.
If you liked Southpaw, you might also enjoy: Creed (2015)
In Bong Joon-ho's bizarre sci-fi satire Okja, Gyllenhaal plays an eccentric television personality who's like a wackier Steve Irwin when the cameras are rolling and a chaotic cartoon character as soon as they're not. A morally corrupt zoologist tasked with declaring (and kidnapping) the best "super pig" for a shady corporation's PR campaign, his character exists as a sort of drunk Ron Burgundy mixed with a hyperactive Muppet, a mustachioed creep who fires off ridiculous one-liners in between yelps and screeches. It's over-the-top and irritating, but as the satirical face of media sensationalism in tandem with corporate greed, Gyllenhaal once again perfectly fits the manic, preposterous tone of the movie.
If you liked Okja, you might also enjoy: Sorry to Bother You (2018)
In David Gordon Green's Stronger, Gyllenhaal embraces the discomfort and fear that PTSD causes in its victims and the people around them. The actor stars as Jeff Bauman, a runner who lost his legs in the Boston Marathon bombing. Between his upbeat Boston accent and overall warm disposition, his trauma still causes him to lash out in anger and terror at his most vulnerable moments.
Gyllenhaal also does an excellent job of highlighting Jeff's exhaustion, with a somber weariness in his eyes that makes his persistence all the more inspiring. Scared and self-loathing, his performance shows how tragedies and incredible stories happen to normal people, not just extraordinary heroes or individuals predisposed to be exceptional, but typical people with strengths, flaws, and insecurities abound.
If you liked Stronger, you might also enjoy: Good Will Hunting (1997)
<i>The Sisters Brothers</i> (2018)
Gyllenhaal portrays a private detective and literal gold digger in 19th-century Oregon in underseen Western The Sisters Brothers, which also stars Joaquin Phoenix and John C. Reilly as brothers hellbent on tracking Gyllenhaal down before he strikes it rich. His character is unlike most men we see in Westerns, as Gyllenhaal plays him with a strange mid-Atlantic accent and a calm, pensive demeanor. There's a charming softness to his presence here, and his reunion with partner-in-crime Riz Ahmed couldn't feel more different than their time together in Nightcrawler — their relationship is now warm, tender, and heartfelt once they realize how much they have in common.
If you liked The Sisters Brothers, you might also enjoy: True Grit (2010)
The high-octane thrills of a Michael Bay project prove to be a perfect match for Gyllenhaal's energy, as the relentless pace and over-the-top tone of Ambulance provide a fitting opportunity for him to embrace the extreme. As the criminal mind behind a multi-million dollar bank heist, his character Danny is so absurd that he borders on parody: yelling most of his dialogue, dripping in sweat for the majority of the movie, and threatening others in almost all of his interactions. His ridiculously condescending tone injects a layer of humor into many of his scenes, but Gyllenhaal simultaneously manages to be so intimidating that he seems like he could snap at any moment with deadly consequences — and he's the chaotic, unpredictable force that keeps the movie moving.
If you liked Ambulance, you might also enjoy: Speed (1994)