Jake Gyllenhaal's 7 Most Underrated Performances

Throughout his career, Jake Gyllenhaal has consistently had an eye for interesting and versatile projects. Although he’d been involved in independent cinema since his breakout years and gained an Academy Award nomination for Brokeback Mountain, it was the failure of Prince of Persia that set Gyllenhaal on his current trajectory. Disillusioned with the creative restrictions of a blockbuster franchise, Gyllenhaal became more selective and increasingly took on challenging parts.

In the decade since Prince of Persia, Gyllenhaal became one of the most exciting actors of his generation. While he’s starred in some of the best films of the past decade, Gyllenhaal’s films haven’t quite reached the “event status” that someone like Leonardo DiCaprio or Daniel Day-Lewis generates. Some of his best work is still criminally underappreciated; poor box office, mixed reviews, bad marketing, and low visibility may all be to blame.

Gyllenhaal will next be seen in Antoine Fuqua’s remake of the Danish thriller The Guilty before taking another stab at the blockbuster world with Michael Bay’s thriller Ambulance and the graphic novel adaptation Oblivion Song. In the meantime, make sure to check out these seven underrated Jake Gyllenhaal performances you may have missed.


Amidst the overblown patriotic war movies of the early 21st century, audiences weren’t sure what to make of Sam Mendes’s cynical Gulf War satire Jarhead. While not directly winking at the audience, Jarhead examines the futility of U.S. soldiers in an environment they don’t belong in. They seek victory and any sense of acknowledgment from their commanding bodies, and the stagnated communication from Washington transforms an idealistic unit into bored, crazed hooligans. Gyllenhaal stars as the lead Private Anthony Swofford, whose memoir inspired the film. He effectively captures the soft soul of someone who wanted to make a difference and is at odds with the exaggerated bro culture that squadmates Peter Sarsgaard and Jamie Foxx represent. While the soldiers’ boredom creates borderline surreal survival scenarios, Gyllenhaal gives the film an emotional gut-punch towards the ending when he returns home disillusioned. His years of training were rendered meaningless with the development of modern warfare technology, and he watches his former brothers-in-arms each return to their sad realities.


Brothers is a showcase piece for Tobey Maguire in a dark, tormented role, but Gyllenhaal is handed an equally challenging task of playing a character who has to gradually earn sympathy. Maguire stars as U.S. Army Captain Sam Cahill, whose disappearance in Afghanistan forces his alcoholic brother Tommy (Gyllenhaal) to care for his wife Grace (Natalie Portman) and their young children. Gyllenhaal doesn’t exaggerate Tommy’s irresponsibilities, but he’s authentically impulsive in the wake of his brother’s presumed death. His initial attraction to Grace is tenderly handled; both are in a sensitive state of mourning, but it sets up an uncomfortable confrontation when Sam returns. While it easily could’ve descended into melodrama, Gyllenhaal brilliantly underplays his emotions as Sam relents. Just as Tommy allows Sam to voice his trauma, Gyllenhaal is generous to give Maguire his standout breakdown scenes without distraction.


Southpaw doesn’t stray too far from formula, and the film hinges on Gyllenhaal to elevate the cornball elements. Southpaw gets darker than a lot of mainstream inspirational sports stories attempt. It follows Gyllenhaal as boxer Billy Hope, who has to overcome a shocking personal tragedy to retain his light heavyweight championship title. It puts Gyllenhaal through a physical and emotional ringer; he got jacked for the role and sells the brutality of Hope’s beatdowns. Gyllenhaal doesn’t exaggerate Hope’s fiery temperament but shows how his anger issues have become destructive, particularly in the relationship with his young daughter (Oona Laurence). The remarkable child star emulates her father’s perpetual rage, an inherited trait that haunts their relationship when she refuses to communicate after protective services separate them. The pair of strong performances bring earnestness to the film, and they hit all the right notes to make the climactic title fight engaging.

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Jean Marc-Vallee’s indie dramedy Demolition takes a lot of bold tonal swings; while landing a few shocking moments of outrageous comedy, the metaphor of a man literally deconstructing his house as he tries to demolish his trauma isn’t exactly a subtle one. Gyllenhaal is able to make the unusual coping methods feel authentic. The obsessive personality of investment banker Davis Mitchell, who loses his wife (Heather Lind) in a freak accident, could’ve grown grating if he amped up the idiosyncrasies. Gyllenhaal shows how each of Davis’ obsessions stem from insecurities he had before his wife’s passing, with the tragedy only accentuating his perceived lack of control. Even the most mawkish of dialogue fits a man who rarely had an original thought, and is only now forced to address his own personal misgivings. Like Southpaw, it’s a case in which his aptitude for emotional reckoning elevates an entire film.


As if Gyllenhaal wasn’t already gravitating towards stories of surviving trauma, Stronger is a remarkably sober look at post-traumatic stress disorder that doesn’t turn coping into a convenient three-act structure. Gyllenhaal’s Jeff Bauman was an irresponsible guy before the Boston Marathon Bombing wrecked his life, and the debilitating loss of his legs don’t immediately amend his flaws. David Gordon Green explores the pressures of living up to a hero status, and as a result watching Bauman heal himself and reckon with his prior behavior is actually inspirational. It’s also more personal; the scenes of Gyllenhaal sharing his experience and meeting other survivors show that his story is just one of many. Unfortunately billed as something more conventional and a box office bomb, Stronger should have been Gyllenhaal’s Best Actor ticket.


Paul Dano’s brilliant directorial debut Wildlife is a sensitive depiction of divorce through the eyes of a child. Showing remarkable restraint with picturesque visuals and frequent long takes, Dano frames the performances in his 1960-set drama through the eyes of young Joe (Ed Oxenbould) as his father Jerry’s (Gyllenhaal) extended work leave sparks his mother Jeanette’s (Carey Mulligan) infidelity. Mulligan is doing career-best work as Jeanette’s rage builds, but Gyllenhaal isn’t given the same prolonged exposure. He’s largely absent from Joe’s memory, and thus is only there for pivotal moments that stand out in his son’s memory. Gyllenhaal excels at the challenge; while not completely oblivious, his consistent attitude as his wife shows obvious signs of disillusionment sows the seeds for the explosive arguments later on.

The Sisters Brothers

The Sisters Brothers is a warm, wonderfully weird western that does pretty much everything to challenge traditional notions of masculinity among gunslingers; don’t let the action-packed trailers fool you, because Jacques Audiard’s film cares less about glamorizing violence as it does showing the tormented souls who inflict it. Joaquin Phoenix and John C. Reilly lead as the titular bounty hunter brothers who search for the inventor Hermann Warm (Riz Ahmed), who is aided by the private detective John Morris (Gyllenhaal). While each of these men wrestles with justifying their professions, they form a tight pact and learn from each other as they search for Warm’s fabled “promise land.” While it ultimately goes in more emotionally devastating directions, seeing these four childish characters earnestly learn about each other is delightful, and Gyllenhaal shines as he forms a protective bond with Warm that emulates the brothers’ dynamic. Reteaming again after Nightcrawler, Gyllenhaal and Ahmed develop a playful relationship that shows a more sympathetic side of both actors.

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About The Author
Liam Gaughan (127 Articles Published)

Liam Gaughan is a film and TV writer at Collider. He has been writing film reviews and news coverage for eight years with bylines at Dallas Observer, About.com, Taste of Cinema, Dallas Morning News, Schmoes Know, Rebel Scum, and Central Track. He aims to get his spec scripts produced and currently writes short films and stage plays. He lives in McKinney, TX.

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