Ranking every Jake Gyllenhaal movie from worst to best is no easy feat, with the actor enjoying a long and successful career to date. Indeed, everyone has their own opinions about which are the worst and best Jake Gyllenhall movies. Born into the Swedish noble Gyllenhaal family, Jake was set up from the very beginning to succeed as an actor due to the continued industry influence of his parents: director Stephen Gyllenhaal and feature screenwriter Naomi Foner. In fact, Gyllenhaal debuted in one of his father's standout films, City Slickers, in which a ten-year-old Jake plays the son of Billy Crystal's (Here Today) Mitch Robbins. Following the release of the new Jake Gyllenhall movie Ambulance on Netflix, it's high time to look back at the actor's work once more.
Although initially typecast as a brooding, moody teen in angsty pictures such as Highway and the cult classic Donnie Darko, Gyllenhaal has since aggressively diversified his acting portfolio. In addition to taking on a wide breadth of challenging roles that have cemented his status as an undoubted A-lister, Gyllenhaal has also performed on Broadway, while picking up a mammoth 30 awards for his various portrayals.
Pulling together a definitive list of Gyllenhaal's movies requires a comprehensive view of his 23 years featuring in no less than 34 starring roles. For expediency, Gyllenhaal's childhood performances will not be considered here, with his turns in City Slickers and A Dangerous Woman at ages ten and thirteen, respectively making his parts in these films rather minor. As a result, here's every Jake Gyllenhaal movie ranked from worst to best, including the most recent releases in the actor's roster.
#34 - Highway
James Cox's failure of an independent drama amounts to little more than an exercise in gathering a group of beautiful actors and then watching them do absolutely nothing memorable across Highway's 97-minute runtime. At its core, Highway attempts to be a coming-of-age movie about three twenty-somethings on the open road who encounter a series of violent and life-changing scenarios along the way. Gyllenhaal plays the incredibly bland Pilot Nelson, whose character amounts to little more than a teen heartthrob devoid of compelling motivation. Even Cox's decision to throw other burgeoning starlets Jared Leto (the DCEU's Joker) and Selma Blair into the mix could not save Highway from its ultimate and unmemorable straight to DVD fate.
#33 - Bubble Boy
The 2001 dark comedy Bubble Boy is only spared the ignominy of rock bottom spot on this list due to the fact Blair Hayes' film tries to do something in a way Highway does not. Unfortunately, what Bubble Boy presents is a tableau of tasteless and crude jokes that only serve to highlight the paper-thin premise of the film. In it, Jake Gyllenhaal plays Jimmy Livingston, a boy forced to live his life in a protective bubble due to his compromised immune system. Based on the 1976 John Travolta-led TV drama The Boy in the Plastic Bubble, Bubble Boy attempts to skew the story in a much lighter direction akin to Seinfeld's classic "Bubble Boy" episode but ends up falling flat on its face with very little wit behind any of its slapstick-inspired comedy.
#32 - Accidental Love
Accidental Love's premise is, on a tertiary level, one that could have been riotous. Alice, a waitress in small-town Indiana, is accidentally shot in the head by a nail gun, but her lack of health insurance renders her unable to have the nail removed, leading to mood swings and hypersexual behavior resulting from brain damage. Alice then heads to Washington, D.C. to campaign for those with bizarre injuries, with the support of Jake Gyllenhaal's unprincipled Congressman Howard Birdwell in tow. Yet, Accidental Love was plagued from the start with issues directly relating to the 2008 financial collapse, with the film's production shut down an unprecedented 14 times due to a series of union and restitution issues. As a result, Accidental Love's final cut was submitted incomplete and missing a series of canceled scenes that conspire to make the film a jarring mess of a satire with little by the way of redeeming qualities.
#31 - Prince of Persia: The Sands of Time
Everything was set up to make Disney's The Prince of Persia videogame adaptation a successful venture, with producer Jerry Bruckheimer stating the film was supposed to be "the new Pirates of the Caribbean." However, lofty ambitions need to be backed up by a product worthy of kickstarting a franchise, and Prince of Persia: The Sands of Time certainly did not deliver on its Disney overseers' vision. It is hard to put a finger on what exactly is wrong with the Prince of Persia film, with a rousing score and well-crafted action scenes making the film at least entertaining upon the first watch. However, Prince of Persia's story has very little soul behind its immense CGI budget, making the narrative's stakes feel so hollow and forced. Gyllenhaal himself addressed the disappointment surrounding the final Prince of Persia product, with the actor candidly stating that he did not "fit perfectly" with the role of Dastan, despite his best efforts.
#30 - Love & Other Drugs
The Jake Gyllenhall movie Love and Other Drugs is certainly a bold film that cheekily pushes the boundaries of an often prudish American romantic comedy genre. The decision to include a series of relatively graphic sex scenes between two A-list stars in Gyllenhaal and Anne Hathaway must be commended for its brazen nature, with the film also tackling the topic of both illegal and prescription drug abuse. It is unfortunate then that the movie writer-director Edward Zwick does not do more with Love and Other Drugs' bold scenes as the film descends into a free-for-all that crudely makes jokes at the sexually inept, repressed, and America's homeless population alike. It must also be said that, despite both actors' pedigree, Gyllenhaal and Hathaway do not have any genuine chemistry on-screen with each other, which makes Love and Other Drugs more of a shock-value project than the romantic comedy it was intended as.
#29 - The Sisters Brothers
The Sisters Brothers is the first film on this list not to be universally panned, with the Western itself being a thoroughly enjoyable romp across America's 1851 landscape. However, The Sisters Brothers constitutes a costly box office bomb for its distributor, Mirror Releasing, with the film failing to capture the attention of both domestic and foreign moviegoing markets alike. This is perhaps best explained by The Sisters Brothers' adamant refusal to pick a narrative lane, with the film neither intense enough to be considered a drama nor funny enough to be considered a comedy, which is also the issue Gyllenhaal's character John Morris suffers from throughout the movie.
#28 - Rendition
The mid-2000s saw Gyllenhaal star in a series of military-based dramas that had decidedly mixed impacts. Rendition is undoubtedly the worst of these as the film centers on the controversial CIA practice of "extraordinary rendition" or, in layman's terms, the transfer and torture of those deemed threats to the United States. The series of sub-plots that run parallel with Rendition's main story actually undermine the film's impact and confuse the viewer simultaneously, making Rendition an anti-war film whose best moments ironically become the taut action sequences associated with America's war on terror.
#27 - Brothers
Brothers is another of Gyllenhaal's aforementioned anti-war drama movies that instead centers around the continued psychological impact of military conflicts on American soldiers. Brothers' leads, Gyllenhaal and Tobey Maguire deserve huge praise for their compelling performances as the casualties-of-war Cahill siblings, but Brothers' finale still falls flat regardless. Brothers makes the crucial mistake of buying too heavily into its own societal importance, meaning its impact as a compelling piece of cinema becomes heavily diminished and appears melodramatic as a result.
#26 - Moonlight Mile
Brad Silberling's romantic drama draws gravitas from the fact it is loosely inspired on his own life experiences, with his girlfriend Rebecca Schaeffer tragically killed by an obsessed fan in 1989. This sobering undercurrent of tragedy leads Moonlight Mile to be a far harder watch than the romance-laden script perhaps suggests, but the film still compels through a series of terrific performances from its lead cast. A young Jake Gyllenhaal (Spider-Man's Mysterio) shines as the bereaved Joe Nast, while Dustin Hoffman and Susan Sarandon lend genuine stardust to Moonlight Mile's slightly contrived story that ensures the film remains a successful piece of cinema to this day.
#25 - The Good Girl
While Jake Gyllenhaal is somewhat typecast in his familiar element of a sullen, troubled, reserved, and enigmatic character in Holden, this is exactly what The Good Girl needs him to be. Jennifer Aniston's role as the depressed Justine Last is a revelation as she moves away from the shroud of Friends' Rachel Green, and Gyllenhaal dovetails with her portrait of a dangerously bored and unsatisfied wife to great effect. Critics roundly praised The Good Girl at the time of its release, and the film's impact as an emotional satire of middle America has not diminished since 2002.
#24 - Wildlife
Paul Dano's (Swiss Army Man) directorial debut is a well-crafted look at a family in crisis that acts as a microcosm for the problems that many married couples continually face. While the story's unassuming scale and slow pace may not appeal to those looking for a more grandiose love story, Gyllenhaal and co-star Carey Mulligan's performances as the heads of the Brinson family demand attention and emotional attachment from audiences. Critics have widely stated Wildlife is Mulligan's strongest performance to date, rivaled only by her enthralling turn in Promising Young Woman.
#23 - Demolition
Though Demolition received a more mixed critical response than other films lower on this list, it is still a hugely compelling examination of the toxic cultures within the bravado-driven world of investment banking. Gyllenhaal's Demolition takes a marriage apart in an often profound portrait of repressed emotion, given life by a standout performance from Gyllenhaal as the unnecessarily stoic Davis Mitchell. While the film's end scene feels like a backward step into contrived territory as Davis watches a physical demolition (that ham-fistedly mirrors the destruction of his emotional barriers), Demolition remains a fascinating piece of work nonetheless.
#22 - Source Code
Source Code is undoubtedly one of 2011's standout films that transcends the familiar trappings of the sci-fi genre and creates a dazzling mind game between its director Duncan Jones and the film's prospective audiences. Gyllenhaal plays Colter Stevens, a U.S. Army captain who is sent into a digital recreation of a real-life train explosion and tasked with figuring out the identity of the terrorist who bombed the train. Source Code's reviews drew high praise from critics upon release, with several citing the plot's close ties to other mind-bending thrillers such as Tony Scott's lauded thriller Déjà Vu.
#21 - Proof
Based on David Auburn's Pulitzer Prize-winning play of the same name, Proof was always destined to be a challenging, yet gratifying piece of cinema. Proof artfully tackles the thin, oft-invisible line between intelligence and madness, evidenced in a series of gripping flashbacks of a brilliant mathematician, Robert Llewellyn (Anthony Hopkins), whose genius is undone by his fast-deteriorating state of mental health. Jake Gyllenhaal's turn as Hal Dobbs is particularly nuanced here, with Hal acting as both confidante and counterbalance to the equally deteriorating Llewellyn sisters (Robert's daughters) and contributing heavily to a balanced and exciting take on psychological pressures of academia.
#20 - Lovely & Amazing
Despite being cast on the bill as a comedy-drama movie, Nicole Holofcener's film translates as far more of an unflinching and accurate look at the personal struggles of the four Marks women in a post-millennium landscape. Lovely and Amazing is such a refreshing piece of cinema as the film often feels chaotic and unbalanced in the same way that real life does, lending further credence to the emotional struggles of its core characters. Kenneth Turan of the Los Angeles Times summed Lovely and Amazing up best with his statement that the movie "is both marvelously observed and completely individual. There is no film like this film." This is high praise indeed and a completely accurate assessment of a movie that often feels more like a fly-on-the-wall look at real people's lives than a film built for viewing en masse.
#19 - The Day After Tomorrow
After his brooding, ferocious breakout in the movie Donnie Darko, Gyllenhaal needed one more film to truly establish himself as a star of the early 2000s amidst a glut of similarly handsome, sullen faces such as Skeet Ulrich and Josh Hartnett. This break materialized as the sci-fi disaster The Day After Tomorrow, in which Gyllenhaal plays Sam Hall, a teen attending an academic decathlon who finds himself trapped in a frozen, apocalyptic New York City after a superstorm heralds in a new ice age in a matter of hours. Gyllenhaal's turn opposite Hollywood stalwarts Dennis Quaid and Ian Holm cemented his place among the big actors of the 21st century and would signal the dawn of a very successful, multi-faceted career. The Day After Tomorrow itself is also the best kind of disaster film, ratcheting up the dread presence of climate change and focusing heavily on the human survival stories that a second ice age would inevitably force into play.
#18 - Everest
In another movie that showcases the fearsome powers of mother nature, Jake Gyllenhaal plays Scott Fischer, an American expedition leader looking to scale Mount Everest ahead of his rival commercial climbing company. Everest tautly, yet faithfully, reenacts the harrowing true story of the 1996 Mount Everest disaster, in which the majority of both the Adventure Consultants' and Mountain Madness' climbing teams perished following an ill-fated ascent to the summit. Everest is as tense as it gets, with director Baltasar Kormákur's dizzying cinematography aiding the sense of dread that quickly envelops this bleakest of true story films.
#17 - Life
While critical approval was far from unanimous for 2017 sci-fi horror Life, the film is a rampant success in exerting pressure and tension in a constantly hushed production akin to silent theatre. Taking place above a futuristic version of the international space station, the film's setting means there is little sound in the film's opening sequences that translates into a pervading sense of dread as Life progresses. Although Life does not necessarily bring any new ideas to the fairly linear narrative of being trapped in space with a malicious life-form, the film feels inspired by, and therefore very akin to, Ridley Scott's masterpiece Alien - and that is a very good thing indeed.
#16 - Ambulance
Ambulance, the new Jake Gyllenhaal movie in which the actor serves as the main antagonist, is proof positive that Michael Bay still has what it takes to make truly compelling blockbusters, even in the era of social justice politics. Indeed, there are several reasons why Ambulance is one of Bay's best movies. Brought to life by the chemistry between Jake Gyllenhaal, Yahya Abdul-Mateen II, and Eiza González, Ambulance is Bayhem at its best, but with its sights set on Gen-Z audiences. Amid impossible car chases and a plot that can only be reasonably described as ridiculous, Ambulance successfully satirizes Bay's own filmography, dives into the ethics of justice, and even tackles how the U.S. government treats its veterans. It's certainly a tall order for what audiences typically expect from a Michael Bay film, but somehow, it never feels like Bay is out of his element. That said, there's a reason for why Ambulance is this far down on a list of the best and worst Jake Gyllenhaal movies: Ambulance is basically just Bayhem 101, except it's aimed at the more socially-tuned-in new adults of the 21st century.
#15 - End Of Watch
Nestled right at the end of the glut of "hidden camera footage" movies spawned from The Blair Witch Project movie's success, End of Watch delivers a refreshing and radically different take on the first-person filming style. Despite the film's rampant action sequences, End of Watch is a carefully planned affair in which writer and director David Ayer is adamant not to fall into any of the usual police movie tropes, with the most obvious being the "buddy cop" dynamic. The gritty and intimate performances delivered by Gyllenhaal and Michael Peña are wholly committed and form the cornerstone of End of Watch's success, even if their respective stories ultimately try a little too hard to memorialize the police work shown on-screen.
#14 - Nocturnal Animals
Nocturnal Animals is a blistering psychological thriller that expertly handles two parallel storylines, with one being in the "real" world and the other focusing on a dark story contained within a mysterious manuscript. The raw emotion of the manuscript delivered to Susan Morrow (The Woman In The Window's Amy Adams) is purposefully translated in a series of visceral tableaus that tell the story of Tony Hastings (Jake Gyllenhaal), a motorist forced into a violent confrontation with a sadistic gang. Gyllenhaal's performance as Tony was singled out for particular praise by critics, who cited the weighting of romanticism and bleakness he imbues the manuscript character with.
#13 - Southpaw
Although Antoine Fuqua's first team-up with Gyllenhaal marks the lesser of the men's two projects together, Southpaw is still an unrelenting tale that hits as hard and fast as its plucky protagonist. Southpaw is not attempting to reinvent the wheel as far as sports dramas go, instead more than content to hit each note of a classic script akin to De Niro's iconic movie Raging Bull. Southpaw also represents one of Gyllenhaal's biggest physical transformations to date, with the actor's absolute commitment to the role of Billy Hope translating into a powerhouse sporting performance.
#12 - Spider-Man: Far From Home
Jon Watts' Spider-Man: Far From Home is the perfect coda to phase 3 of the MCU, wrapping up the events of Avengers: Endgame while also cementing Tom Holland's Peter Parker as arguably the most popular Spidey to date. The beauty of Far From Home is that it feels less like a high-stakes superhero movie and more like a teen romance flick with smatterings of action and loss to elevate the film's emotionally driven plot. Gyllenhaal is perfect for the role of Quentin Beck (and later Mysterio), a superhero who eventually reveals his true, sinister machinations, making Far From Home a must-see for any Marvel fans, whether chronologically viewing the MCU or not.
#11 - Prisoners
Before Arrival, Blade Runner 2049, and Dune, Denis Villeneuve directed the gritty Prisoners, which focuses on the abduction of two young girls in Pennsylvania and the subsequent search for the suspected abductor by the police. Prisoners' plot is interesting enough, yet the layered and often polarizing character development woven into the film makes Prisoners such a compelling watch. The casting for Prisoners is also spot on, with Hugh Jackman and Gyllenhaal both cited for their Oscar-worthy performances at the time of the film's release.
#10 - Enemy
Denis Villeneuve clearly felt he was onto a winning relationship with Gyllenhaal, bringing the actor back for Enemy in 2013 just one year after the pair enjoyed such success with the taut thriller Prisoners. Yet, Enemy is a vast step up from the pair's already fine work and a truly haunting film to boot. Enemy's style is unsettling and lurid as it harks to the work of a David Lynch movie from yesteryear, but the film cements itself as a modern classic due to its genuinely terrifying ending that lingers in the mind long after Villeneuve's thriller comes to a close.
#9 - Okja
Now moving into classic territory, number nine on this list is reserved for the surreal-yet-touching story of super-pig Okja, the subject of malicious intentions from doctors and butchers alike. Director Bong Joon-Ho has little to prove after a series of masterfully emotional stories (the epitome being Memories of Murder), yet Okja's tug-on-your-heartstrings commentary on animal cruelty undoubtedly makes it a truly unique piece of cinema that forces introspection amongst its audiences. The film's initial narrative question of whether Okja possesses a soul quickly becomes no query at all as this Bong Joon-Ho movie renders the viewer at his mercy before going about telling a grippy story of contemporary corruption and greed.
#8 - Zodiac
The true genius of David Fincher's Zodiac is that it lures the viewer into a carefully crafted 1970s imitation before ratcheting up the anxiety surrounding the seemingly spectral Zodiac killer. Fincher's attention to detail around the true-life crimes is spine-tingling, with Zodiac's ambiguous ending mirroring the confusion that still surrounds the killer's true identity today. Gyllenhaal's performance as the obsessive Robert Graysmith is outstanding as he navigates the labyrinth of facts that made the real Zodiac killer so elusive all those years ago, making Zodiac a chiller of the highest order as a result.
#7 - October Sky
October Sky is a major movie, home to Jake Gyllenhaal's breakout role and an incredibly moving tale rooted in deep, wholesome values. The brilliance of October Sky is that it resists the tendency to make a villain of its paternal figures, instead painting characters like John Hickam as caring yet unable to understand the entire emotional spectrum that his teenage son is experiencing. This limited paternal vision makes October Sky's premise land amongst any demographic, engendering an emotional connection with parents worldwide that transcends the bounds of a normal film to audience relationship.
#6 - Jarhead
Jarhead carries with it an emotional gravitas befitting the 2003 memoir from which Sam Mendes' war movie was adapted, with Jake Gyllenhaal thrust to the fore as U.S. Marine Anthony Swofford. This film, above most others, exemplifies Gyllenhaal's ability to act a foil for the talents of the other actors around him, with Swofford's story at times becoming a prism that shines a light on the other Marines he served with in the Gulf War. Jarhead is stirring stuff, and translates as a modern war drama that highlights the ultimate redundancies of human troops on the ground in the modern age while also displaying the harrowing psychological effects war has on many of its surviving veterans.
#5 - Brokeback Mountain
It is not understating Ang Lee's neo-western romance to say that Brokeback Mountain is a watershed film that marks the turning point for the advancement of queer cinema into mainstream consideration in 2005. This timeless Ang Lee movie of forbidden romance and unrequited love took home a landslide of three Academy Awards and four Golden Globes, with several owed to the virtuoso performances of Heath Ledger and Gyllenhaal as the passionate, yet conflicted Del Mar and Twist. Brokeback Mountain has since been selected for preservation in the United States' National Film Registry by the Library of Congress after being rightfully marked as "culturally, historically, and aesthetically significant."
#4 - Velvet Buzzsaw
Dan Gilroy returns five years after his explosive collaboration with Gyllenhaal (Nightcrawler) to deliver Velvet Buzzsaw, a film that is simply the epitome of everything a satirical sideswipe should be. The film's fictitious Vetril Dease paintings are enthralling even as their own entities, yet it is the way Netflix's Velvet Buzzsaw establishes taste as the only valuable commodity in a vapid send-up of Los Angeles' art culture that truly makes the movie transcendent. Gyllenhaal's Morf and Toni Collette's Gretchen epitomize this idea, trading art and slander in equal measure. While Velvet Buzzsaw's horror tag feels largely unearned, viewing the film as a commentary on the soulless nature of modern artistic tendencies guarantees Velvet Buzzsaw lingers long in the memory as a unique piece of cinema from Dan Gilroy.
#3 - The Guilty
If End of Watch places the police force on a pedestal, then The Guilty tears it down in the most compelling fashion while being wholly designed to capture the vitriol within the current zeitgeist. A remake of the 2018 Danish film of the same name, Antoine Fuqua's The Guilty is the perfect platform for Gyllenhaal to loudly voice his well-publicized political views. Gyllenhaal's performance as troubled and disgraced dispatch officer Joe Baylor is as emphatic as it is appalling as the audience is forced to confront the dire consequences of Joe's rash and reckless behavior time and again.
#2 - Donnie Darko
Donnie Darko is a heady blend of menace and teen angst that combines into a deeply emotional and dizzying film. The movie that put Jake Gyllenhaal on the proverbial map for good, Donnie Darko is such an enigmatic film due to the fact it inspires different emotions in each audience that views it, leading Richard Kelly's film to be considered as much a work of art think-piece as a suburban psychological thriller. The highest praise for Donnie Darko is the film's timeline, which saw the film struggling commercially upon release before becoming an ultimate cult classic whose relevance fails to diminish after each viewing. The mind twists differently each time Frank compels Donnie to commit terrible acts in Middlesex to create a truly outstanding and timeless piece of cinema.
#1 - Nightcrawler
Dan Gilroy's directorial debut is mesmerizing, not least because his vision for the film was adapted to the screen completely untarnished by studio meddling or narrative tweaks. The "Stringer" profession of Gyllenhaal's Lou Bloom belies a symbiotic relationship between unethical journalism and consumer demand that is repeatedly driven home over the course of Nightcrawler's story. Nightcrawler demands introspection of the most uncomfortable order, with every snap of Bloom's camera further querying the bloodthirsty nature of the modern news media cycle. Gyllenhaal, in particular, was singled out for his performance that has been compared to the towering Robert DeNiro in Taxi Driver and cited as a "bravura, career-changing tour-de-force" for the actor. The violence that bubbles under the surface of Nightcrawler's narrative aggressively seeks attention from start to finish, making the Jake Gyllenhaal-led thriller a near-perfect and chilling film for the ages.