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Jake Gyllenhaal’s 9 Best Performances

Jake Gyllenhaal's 9 Best Performances

[Editor’s Note: This post is presented in partnership with Movies On Demand. Catch up on this year’s Awards Season contenders and past winners On Demand. Today’s selection is “Nightcrawler.” Here are our picks for Jake Gyllenhaal’s best roles.]

In “Nightcrawler,” Jake Gyllenhaal delivers a scorching turn as Lou Bloom, a modern-day Travis Bickle who prowls the LA streets with a camera, hungry for the next big, explosive, headline-snatching scoop. Gyllenhaal, who went gaunt for this creepy SAG and Golden Globe-nominated role, narrowly missed an Oscar nom for this antiheroic creature of the night who embodies our own culture’s fetishes and fascinations with great, bloody spectacle. As his cutthroat TV-news boss (Rene Russo) tells him, “If it bleeds it leads,” and wannabe crime-journo Lou is more than up to the task of meeting her demands for the sensational and lurid.

In honor of the film’s VOD premiere this week, here are a few of his best performances.

Enemy” (2014) – Adam & Anthony


Arguably Gyllenhaal’s strangest leading-man vehicle since 2001’s “Donnie Darko,” “Enemy,” directed by Denis Villeneuve, juggles postmodern pyrotechnic flourishes with a classic Hitchcock-thriller formula. In a dual performance, he plays Adam Bell, a withdrawn history professor entwined in dead-end relationship with Melanie Laurent’s Hitchcock-blonde Mary, and night after listless night of emptiness; but he’s thrust out of his cycle of torpidity when he sees a carbon copy of himself kicking it as an extra in a B-movie. Things take take kinky, twisty turns as he chooses to confront his doppelgänger, and Gyllenhaal is more than up to the task of conveying the film’s slick existential menace. 

Prisoners” (2013) – Detective Loki

“Prisoners” marked the beginning of Gyllenhaal’s fruitful partnership with Canadian director Denis Villeneuve. A good ole fashioned procedural thriller, the film shows the actor flexing his dramatic muscles more than ever before, proving that he’s most skilled at playing a black hole of a human being. He throws himself into the role of the brooding, windswept Detective Loki, who’s investigating the dubious kidnapping of two young girls. In a film studded with red herrings and narrative dead-ends, Gyllenhaal effectively mirrors our own frustrations with the maze-like sequence of events. Loki harbors a lot of vaguely sourced guilt on his shoulders, but Gyllenhaal clearly doesn’t need a backstory to furnish his character.

End of Watch” (2012) – Brian Taylor

Gyllenhaal underwent months of intensive training to assume the role of an LAPD officer working the tough South Central LA streets in David Ayer’s bracing, kinetic police procedural. Opposite Michael Pena as his partner-in-crime-fighting, he’s the kind of earnest, goodhearted cop we rarely see in the genre, which makes the tragic climax all the more potent. Gyllenhaal’s naturalism chops are in fine form in the freewheeling ride-alongs he shares with Pena’s Miguel Zavala, shot with arresting, in-your-face style by Roman Vasyanov.

Zodiac” (2007) – Robert Graysmith

With steely reserve, Gyllenhaal plays ’70s San Francisco chronicle cartoonist Robert Graysmith, whose fascination with the enigmatic Zodiac killer culminated in a nonfiction tome that serves the basis for David Fincher’s sprawling Bay Area thriller. Graysmith is an obsessive, combing over arcane clues, details, facts and figures before realizing he’s in too deep. Gyllenhaal’s a bit of a cypher, but his screen chemistry with Robert Downey, Jr. as hard-swilling Chronicle crime reporter Paul Avery is one of the film’s many pleasures.

“Jarhead” (2005) – Anthony Swofford

Gyllenhaal plays real-life former-US Marine Anthony Swofford in Sam Mendes’ minor, yet viscerally impactful, Gulf War film. A wayward kid who drifts into military life almost as a lark before grasping the massive psychological fallout he’s about to endure, Gyllenhaal ably conveys the doldrum life of a soldier, with all the boredom and the listless hurry-up-and-wait armed conflict entails. Even when Swofford descends into full-blown PTSD meltdown mode, Gyllenhaal brings an earthly, primal sexuality to the film as repressed bitterness toward his back-at-home girlfriend boils to the surface.

Brokeback Mountain” (2005) – Jack Twist


Jake Gyllenhaal is the emotional epicenter of Ang Lee’s shattering revisionist Western romance. As repressed ranch hand Jack Twist, he communicates the pangs of closeted gay longing even when his is-he-or-isn’t-he sexuality resist ever being fully spelled out. Gyllenhaal is especially affecting when keying into Jack’s sexual ambivalence, wanting and dreaming of an impossible life with Ennis (Heath Ledger) while also tangling with his fraught home-life, in which he must play the part of heterosexual husband to his wife Lureen (Anne Hathaway), who knows more than she lets on. The “I wish I knew how to quit you” speech, culturally kitschified as it may be, still puts a lump in the throat ten years later. This remains his only Academy Award-nominated performance.

“The Good Girl” (2002) – Holden Wurther

Miguel Arteta’s under-appreciated Jennifer Aniston vehicle may look a tinge dated in hindsight, but what stands out are the performances. In a dustbowl Texas town, Retail Rodeo cashier Justine (Aniston) wants more. Enter much younger, sexy and dark-souled Holden (Gyllenhaal), who initiates a workaday affair under the nose of her oblivious, blue-collar husband (John C. Reilly). Holden’s a depressive and some of his character beats, including that he’s always reading a copy of “The Catcher in the Rye” and that he named himself after its protagonist. But Gyllenhaal brings psychological heft to the role, demonstrating his preternatural gifts as a rising young star.

“Donnie Darko” (2001) – Donnie Darko 

It’s hard to believe that, at age 20, Jake Gyllenhaal’s breakout debuted just shy of 15 years ago. While Richard Kelly’s cult oddity may have eroded against the cruel sands of time, Gyllenhaal’s magnetic turn as a sly high schooler with preternatural visions who turns out to be a harbinger of time-spanning doom still stands as iconic. It’s easy to see why Jena Malone’s damsel in distress falls for him: he’s got sociopathic charm in spades— even when an imaginary talking bunny is urging him to do murder and mayhem.

Indiewire has partnered with Movies On Demand for Indiewire’s Awards Season Spotlight. Meet the nominees and watch the movies with Movies On Demand. Go HERE for profiles, Contender Conversations, Awards news, and viewing guides for your complete Awards Season experience.

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