The best Jake Gyllenhaal The films show how impressive the actor's career has been. He debuted in one of his father's (director Stephen Gyllenhaal) prominent films, City Slickers and never looked back. Although initially typecast as a brooding, moody teenager in harrowing pictures such as the twisty cult classic Donnie DarkoSince then, Gyllenhaal has aggressively diversified his acting portfolio. In addition to taking on a wide range of challenging roles that have cemented his status as an undisputed A-lister, Gyllenhaal has also performed on Broadway, while winning a mammoth 30 awards for his various performances.
Putting together a definitive list of Gyllenhaal's films requires a comprehensive look at his two-decade-plus career, so only his films with leading roles are considered. Much of his work as a child saw him appear only briefly on screen and in minor roles. Once he started landing supporting and leading roles, Gyllenhaal's career took off and he has since become one of the most recognized and respected actors of his generation.
37
Highway (2002)
Pilot Kelson
James Cox's indie drama amounts to little more than an exercise in bringing together a group of handsome actors and then watching them do nothing memorable. Highwayduration of 97 minutes. In essence, Highway tries to be a coming-of-age film about three 20-somethings on the road who encounter a series of violent and life-changing scenarios along the way, but it mostly misses the mark
Gyllenhaal plays Pilot Nelson, whose character is little more than a teenage heartthrob devoid of convincing motivation. Even Cox's decision to include other rising stars of the time, such as Jared Leto and Selma Blair, failed to save Highway of its final and memorable direct-to-DVD fate. Although the film doesn't have enough reviews on Rotten Tomatoes for an official rating, audiences were happier with it than critics at 69%.
36
Bubble Boy (2001)
Jimmy Livingston
One of the first notable films in Jake Gyllenhaal's career as a leading man saw him star in the comedy bubble boy. Unfortunately, what bubble boy present is a cadre of often tasteless and crude jokes that only serve to highlight the film's fragile premise. In it, Jake Gyllenhaal plays Jimmy Livingston, a boy forced to live in a protective bubble due to his compromised immune system.
The film ended up being panned by critics and failed to recoup its budget at the box office.
Based on the 1976 John Travolta-led TV drama The boy in the plastic bubble, bubble boy tries to twist the story in a much lighter direction, similar to SeinfeldThe classic “Bubble Boy” episode, but ultimately falls flat with very little intelligence behind any of its slapstick-inspired comedy. The film ended up being panned by critics and failed to recoup its budget at the box office. Gyllenhaal avoided comedic roles for a while afterward.
35
Accidental Love (2015)
Howard Birdwell
Accidental loveThe premise of is wild. Alice, a waitress in small-town Indiana, is accidentally shot in the head with a nail gun, but her lack of health insurance makes her unable to remove the nail, 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.
Despite this premise, Accidental love was plagued from the start by issues directly related to the 2008 financial collapse, with Production on the film was halted an unprecedented 14 times due to a range of union and restitution issues. As a result, Accidental loveThe final version of was sent incomplete and missing a number of canceled scenes that sometimes conspire to make the film a mess. Biel and Gyllenhaal were good in what actually appeared on screen.
34
Prince of Persia: The Sands of Time (2010)
Dastan
Everything has been prepared to make Disney's The Prince of Persia the video game adaptation was a successful venture, with producer Jerry Bruckheimer stating that the film should be "the new Pirates of the Caribbean." However, the lofty ambitions were not fully supported and Prince of Persia: The Sands of Time did not fulfill the vision of his Disney supervisors. It's difficult to pinpoint what exactly caused the film's problems, with a rousing soundtrack and well-crafted action scenes making the film at least entertaining on first viewing.
However, Prince of PersiaThe story has very little soul behind its huge CGI budget, making the stakes of the narrative feel so empty and forced. Gyllenhaal himself addressed the disappointment surrounding the final Prince of Persia productwith the actor openly stating that he doesn't "fits perfectly" with the role of Dastan, despite his best efforts.
33
Surrender (2007)
Douglas Freeman
In the mid-2000s, Gyllenhaal starred in a series of military dramas that had decidedly mixed impacts. Capitulation is often considered the worst of them, as it got a mixed response at best. The film focuses on the CIA's controversial practice of “extraordinary rendition” or, in layman's terms, the transfer and torture of those considered threats to the United States. It's not exactly new ground to explore on the big screen and has been done better elsewhere.
The issue here was the series of parallel subplots Capitulationmain story.
The issue here was the series of parallel subplots Capitulationmain story. In fact, they undermine the impact of the film and confuse the viewer at the same time.doing Capitulation an anti-war film whose best moments, ironically, become the tense action sequences associated with America's war on terror. This undermines the work of the talented cast, as Gyllenhaal shares the screen with Reese Witherspoon, Meryl Streep and more.
32
Moonlight Mile (2002)
Joe Nast
Brad Silberling's romantic drama attracts attention because it is loosely inspired by his own life experiences. The story is inspired by his girlfriend Rebecca Schaeffer and when she was tragically killed by an obsessed fan in 1989. This worrying trend of tragedy leads Moonlight Mile be a much more difficult watch than the romance-laden script might suggestbut the film draws a number of incredible performances from its main cast.
A young Jake Gyllenhaal shines as the grieving Joe Nast, while Dustin Hoffman and Susan Sarandon lend genuine stardust to Moonlight MileThe slightly contrived story that ensures the film remains a successful piece of cinema to this day. Up until this point, Gyllenhaal was apparently still trying to find his place in Hollywood and found it soon after, with his performance here likely playing a major role in his emergence.
31
Love and Other Drugs (2010)
Jamie Randall
Love and other drugs is certainly a bold film that shamelessly pushes the boundaries of an often prudish American romantic comedy genre. The decision to include a series of relatively explicit sex scenes between two A-list stars, Jake Gyllenhaal and Anne Hathaway, is to be commended for its brazen nature, with the film also touching on the topic of illegal and prescription drug abuse. There was a lot of potential in the premise and the people involved.
Although the film received a mixed response from fans and critics, both Gyllenhaal and Hathaway received Golden Globe nominations for their performances.
That's it It's regrettable then that film director and screenwriter Edward Zwick doesn't do more with Love and other drugs'daring scenes as the film turns into a free-for-all that makes crude jokes at both America's sexually inept, repressed and homeless population. Although the film received a mixed response from fans and critics, both Gyllenhaal and Hathaway received Golden Globe nominations for their performances.
30
Strange World (2022)
Researcher clade
Finding a forgettable Walt Disney animated film is difficult, as the studio is known for releasing classics. Unfortunately, Strange World It is a rare case of one of his films being a commercial failure as it did not recoup its budget and went unnoticed. The film revolves around a family of explorers, including Gyllenhaal's Clade as the protagonist, who embark on a mission to save the planet Pando.
For the most part, reception Strange World It was solid enough by critics, holding a 72% on Rotten Tomatoes. It received praise for its voice acting and portrayal, as it featured the studio's first openly gay key character. That said, it was a rare release from the studio not to receive an Oscar nomination for Best Animated Feature and was considered a disappointment following the success of Charm.
29
House on the Road (2024)
Elwood Dalton
Films from the 80s and 90s are being remade more and more these days and one of the most recent was Road house. A remake of the beloved 1989 Patrick Swayze film of the same name, this take saw Jake Gyllenhaal take on the lead role and show off some of his physical skills. The simple premise sees Gyllenhaal's Elwood Dalton, a former UFC fighter, getting a job as a security guard.
This isn't Gyllenhaal's first time playing a fighter, so it's something he did well and his battle scenes are the highlight of the film. Conor McGregor may not be your average actor, but his true UFC credentials and over-the-top acting made him a fun antagonist for Gyllenhaal to play. Like the original, 2024 Road house received a mixed response, but remains the kind of film that audiences can have fun watching.
28
The Brothers Sisters (2018)
John Morris
Like many actors before him, Jake Gyllenhaal tried his hand at starring in a Western in 2018 The Sisters Brothers. The film itself is a thoroughly entertaining romp through the American landscape of 1851, where Gyllenhaal plays a detective named John Morris. However, The Sisters Brothers was an expensive box office bomb for its distributor, Mirror Releasing, with the film failing to capture the attention of domestic and foreign film markets.
This is perhaps best explained by The Sisters Brothers' adamant refusal to choose a narrative path, with the film is not intense enough to be considered a drama, nor funny enough to be considered a comedy. This is also the problem that Gyllenhaal's character, John Morris, suffers from throughout the film. John C. Reilly and Joaquin Phoenix, the titular Sisters Brothers, were praised for their performances as stars of this well-received project.
27
Brothers (2009)
Tommy Cahill
Brothers is another of Gyllenhaal's aforementioned anti-war drama films that instead revolves around the ongoing psychological impact of military conflicts on American soldiers. The plot revolves around Gyllenhaal's Tommy and Natalie Portman's Grace coming together after Tommy's brother and Grace's husband Sam (Tobey Maguire) dies in the war, with the two eventually falling in love. When it's revealed that Sam is actually alive, the real drama begins.
Brothers clues, Gyllenhaal and Tobey Maguire deserve high praise for their convincing performances as the war-torn Cahill brothers.but the film has problems with its ending. Many reviews criticized the film's third act and ending, suggesting that it reduced the overall quality. Brothers it makes the crucial mistake of believing too much in its own social importance, which means that its impact as a compelling piece of cinema is greatly diminished and, as a result, it comes across as melodramatic.
26
The Good Girl (2002)
Thomas "Holden" Worther
2002 was a big year for Jake Gyllenhaal, as he delivered strong performances that set the tone for his future. Although Gyllenhaal is somewhat stereotypical in his familiar element of the brooding, troubled, reserved, and enigmatic character who believes he is Holden Caulfield incarnate, that is exactly what The good girl needs him to be. The film follows him as he begins a relationship with a store clerk.
Jennifer Aniston's role as the depressed Justine Last was a revelation as she stepped away from the shroud Friends' Rachel Green and showed off some impressive dramatic moves. Meanwhile, Gyllenhaal fits his portrayal of a dangerously bored and dissatisfied wife to great effect. Critics widely praised The good girl at the time of its releaseand the film's impact as an emotional satire of Central America has not diminished since 2002.
25
Wildlife (2018)
Jerry Brinson
He is now best known for his role as The Riddler in Batman but Paul Dano has long been a talented actor who also got behind the camera to wild animals. His directorial debut is a well-crafted look at a family in crisis that acts as a microcosm for the problems many couples continually face. Based on a 1990 novel of the same name, the story's unassuming scale and slow pace may not appeal to those looking for a grander love story.
However, Jake Gyllenhaal and Carey Mulligan's performances as the heads of the Brinson family demand the audience's attention and emotional attachment. Critics have widely declared wild animals is Mulligan's strongest performance to date, rivaled only by her riveting performance in Promising Young Womanwhich is a huge compliment. Meanwhile, it marks another excellent subdued effort from Gyllenhaal at this point in his career.
24
Demolition (2015)
Davis Mitchell
2015 Demolition is a supremely compelling examination of the toxic cultures in the world of investment banking, fueled by bravado, which helps it stand out in Jake Gyllenhaal's filmography. It's the kind of film that may not have received widespread acclaim when it was released, but is better watched over time. Gyllenhaal Demolition dismantles a marriage into an often profound portrait of repressed emotions, comes to life with a standout performance from Gyllenhaal like the unnecessarily stoic Davis Mitchell.
The fact that Gyllenhaal delivers such a remarkable performance as a character who isn't known for emoting much on screen is a testament to his acting skills. Although the film's final scene feels like a step back into made-up territory as Davis watches a physical demolition (which awkwardly reflects the destruction of his emotional barriers), Demolition it remains fascinating work, however.
23
Proof (2005)
Harold Dobbs
Based on David Auburn's Pulitzer Prize-winning play of the same name Proof It was always destined to be a challenging but rewarding piece of cinema. The unknown film follows a woman who struggles with the belief that she may have inherited her father's mental illness. Proof deftly addresses the fine and often invisible line between intelligence and madnessevidenced in a series of gripping flashbacks to a brilliant mathematician, Robert Llewellyn (Anthony Hopkins), whose genius is undone by his rapidly deteriorating mental health.
Jake Gyllenhaal has a supporting role as Hal Dobbs and is particularly nuanced here. Hal acts as confidant and counterbalance to the equally deteriorated Llewellyn sisters (Robert's daughters) and contributes strongly to a balanced and moving approach to the psychological pressures of academia. The reception was strong here, with Paltrow receiving a Golden Globe nomination for her efforts.
22
Velvet Circular Saw (2019)
Morf Vandewalt
Dan Gilroy returns five years after his explosive collaboration with Gyllenhaal (Image: Disclosure)Nocturnal) to deliver Velvet circular sawa film that is simply the epitome of everything a satirical jab should be. The film's fictional Vetril Dease paintings are fascinating even as their own entities, but that's how Netflix Velvet circular saw establishes taste as the only valuable commodity in a bland conveyance of Los Angeles art culture that truly makes the film transcendent.
Gyllenhaal's Morf and Toni Collette's Gretchen epitomize this idea, trading art and slander in equal measure. While Velvet circular sawhorror tag seems largely unearned, viewing the film as a commentary on the soulless nature of modern artistic trends warrants Velvet circular saw remains long in memory as a unique piece of cinema by Dan Gilroy. Reviews were mostly mixed at the time of release and the solid film was somewhat forgotten.
21
Lovely and Amazing (2001)
Jordan
Despite being cast as a comedy-drama film, Nicole Holofcener's film translates much more as an unflinching and accurate look at the personal struggles of the four Marks women in a post-millennium landscape. Adorable and amazing is such a refreshing piece of cinema, as the film often feels chaotic and unbalanced in the same way as real life, lending more credibility to the emotional struggles of its main characters.
The film tells the story of four different women in a family as they deal with insecurities and seek redemption in different ways. Gyllenhaal has a role as Jordana teenager with whom Michelle (Catherine Keener) has sex, which leads to her being arrested. Although her role was small, the film was still highly praised and saw most of the cast receive notable award nominations.
20
Life (2017)
Dr David Jordan
While critical approval is far from unanimous for 2017's sci-fi horror Lifethe film is a runaway success in exerting pressure and tension in a constantly silent production, similar to silent theater. The plot follows a six-member crew in space who discover the first evidence of alien life forms. Taking place above a futuristic version of the international space station, the film's setting means that there is little sound in the film's opening sequences, which translates into a pervasive sense of dread as Life progresses.
Jake Gyllenhaal plays Dr. David Jordan, the ISS medical officer who is often confused in this tense situation. Although Life doesn't necessarily bring any new ideas to the rather linear narrative of being trapped in space with a malicious life form, the film feels inspired by Ridley Scott's masterpiece Foreigner, which is a good thing. Gyllenhaal is joined by a strong cast that includes Ryan Reynolds and Rebecca Ferguson.
19
The Day After Tomorrow (2004)
Sam Hall
After his sullen and ferocious escape into Donnie DarkoGyllenhaal needed one more film to truly establish himself as a star of the early 2000s. This breakthrough materialized as the sci-fi disaster The day after tomorrowin which Gyllenhaal plays Sam Hall, a teenager participating in an academic decathlon who finds himself trapped in a frozen, apocalyptic New York City after a superstorm heralds a new ice age in a matter of hours.
The day after tomorrow It's also the best kind of disaster movie in itself...
Gyllenhaal's turn opposite Hollywood stalwarts Dennis Quaid and Ian Holm cemented his place among the great actors of the 21st century and would signal the beginning of a multifaceted and highly successful career. The day after tomorrow It's also the best kind of disaster movie itself, heightening the terrifying presence of climate change and focusing heavily on the stories of human survival that a second ice age would inevitably force onto the scene.
18
Everest (2015)
Scott Fischer
In another film that showcases the fearsome powers of Mother Nature, Jake Gyllenhaal plays Scott Fischer, an American expedition leader seeking to climb Mount Everest at the head of his rival commercial climbing company. Everest tensely but faithfully reenacts the harrowing true story of the 1996 Mount Everest disasterin which most of the Adventure Consultants and Mountain Madness climbing teams died after an ill-fated summit climb.
This means Gyllenhaal is playing a real person, something he hasn't done often in his career, further showcasing his versatility. Everest is as tense as it gets, with director Baltasar Kormákur's dizzying cinematography aiding the sense of dread that quickly envelops this darkest of true-story films. Although the visual effects were the most praised aspect of the film, the performances were also strong.