The activeness thrillerAmbulanceis Jake Gyllenhaal ’s latest movie and has him toy a desperate criminal in an increasingly acute situation . Though Gyllenhaal can be the typical Hollywood run world , he also seems to have a lot of fun playing the less than heroic characters .

There are a smorgasbord of persona in which Gyllenhaal has embrace darker case . Some of them are somewhat misunderstood yet flawed people , others are grounded and blemished humans , and some are larger - than - life baddies . Looking at these past Gyllenhaal roles , some are more villainous than others .

John Morris - The Sisters Brothers (2018)

The WesternThe Sisters Brothersstars John C. Reilly and Joaquin Phoenix as a dyad of hired gun for hire sent to track down and kill the man who slip money from their gangster boss . Gyllenhaal plays John Morris , another of the mobster ’s employee who is charge to site the aim of the blackwash .

apparently , Morris ’s line of work is less than moral and he play some role in having mass shoot down or harm . But he is also intelligibly a gentler person than the workplace usually fee-tail . He also ends up take form a legitimate friendship with the man he ’s meant to be tracking .

Anthony - Enemy (2013)

The psychological thrillerEnemyfrom Denis Villeneuve has Gyllenhaal wager double duty . His first use is of Adam , a instructor who discovers another man , Anthony , who is his exact double , populate his own life in the same metropolis .

While the discovery lead to both work force doing some questionable things , Anthony seems to be the speculative of the two . He is register to be a operator of women , an adulterer , and someone who his wife regard as a bad person .

Morf Vandewalt - Velvet Buzzsaw (2019)

The thrillerVelvet Buzzsawis a creepy account rig in the art world and mall on a group of art curators who slip the painting of a dead artist and begin selling them . But soon they are picked off one by one by inscrutable supernatural forces .

Gyllenhaal dally one of the art thieves seeking to profit off of a dead man ’s work so he is immediately not very likeable . However , to Morf Vandewalt ’s credit rating , he does seek to put a stop to it when citizenry start dying , probably out of concern for himself .

Howard Birdwell - Accidental Love (2015)

Despite coming fromOscar - nominated filmmaker David O. Russell , Accidental Lovewas not seen by many multitude as it confront a lot of behind - the - scenes play . The comedy star Jessica Biel as a fair sex who is shot in the head with a nail gun and Gyllenhaal as the unscrupulous representative who brings her outlandish problem to Washington .

As Howard Birdwell , Gyllenhaal has a lot of merriment play the typical sleazy pol . His concern with this woman is only a show to further his own political life history in a disgraceful means .

Joe Baylor - The Guilty (2021)

The recent thrillerThe Guiltyis a rattling video display of Gyllenhaal ’s outstanding natural endowment while also give him a very complex character to play . Jon Baylor is a Los Angeles constabulary police officer who , follow an incident in the telephone circuit of duty , is attribute as a 911 operator pending the trial .

After getting a call from a woman who has apparently been kidnapped , Baylor does everything he can to save her . However , his aggression and short temper sometimes make the spot worse . In the end , he is let on to be a very flawed valet de chambre who , at the very least , is unforced to confront the penalisation he deserves .

Danny Sharp - Ambulance (2022)

Gyllenhaal play Danny Sharp inMichael Bay ’s fresh action - thrillerAmbulance . He is a career criminal who cares for his adoptive brother , Will , yet proves to be a rash and deadly person when push .

He is clearly a spoiled influence , convincing Will to join him in his crime . But after a armed robbery go wrong , Danny really shows how grievous he is as he is quick to pop anyone who gets in his agency of making it to exemption with his money .

Johnny Wilcox - Okja (2017)

Beforemaking Oscar chronicle withParasite , Bong Joon - ho directed the wild dangerous undertaking movieOkja . The movie follows a vernal girl live in a rural Korean village whose best protagonist , a giant pig , is captured . Gyllenhaal has a small but memorable purpose as Johnny Wilcox .

Wilcox is the gonzo spokesman for an brute rights organization but is also a monolithic hypocrite . Though he speaks passionately on behalf of the brute , once away from the public , he evince that he does n’t care at all about them or the hurt they bear .

Quentin Beck/Mysterio - Spider-Man: Far From Home (2019)

Initially , Quentin Beck aka Mysterio is introduced as an ally to Peter Parker inSpider - Man : Far From Home . After misplace his wise man Tony Stark , Peter is thrilled to have an older hero to guide him as they save the human beings together .

But Beck is eventually let on to be a disgruntled Stark Technologies employee who seek to put on powerful tech by manufacturing a ball-shaped threat . He is also willing to obliterate Peter and many more destitute people in gild to succeed . And in the end , he still gain ground in a way as he divulge Spider - Man ’s personal identity to the human beings .

Louis Bloom - Nightcrawler (2014)

Though Mysterio might be a villain on a grander shell , Louis Bloom fromNightcrawleris the most remorseless and perturbing character Gyllenhaal has act . He is also a very ambitious man who seeks to make a name for himself in the man of television journalism .

Bloom proves himself to be a instinctive for the cutthroat commercial enterprise thanks to his deficiency of ethical motive . He bends the legal philosophy , blackmails , and even has citizenry killed just to ensure his own route to succeeder .

NEXT : Jake Gyllenhaal ’s 10 Best Movies , According to Ranker

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A collage image of Luke Skywalker in A New Hope

Sidious, Tyranus, Maul, and Vader.

Split image of Jake Gyllenhaal in Enemy, Ambulance and Spider-Man: Far From Home

Jake Gyllenhaal as John Morris in The Sisters Brothers

Jake Gyllenhal as Adam and Anthony in Enemy 2014

Morf analyzes a piece while Rhodora looks at him

jake gyllenhaal accidental love

Jake Gyllenhaal as Joe Baylor wearing a headset on the emergency call in The Guilty

Jake Gyllenhaal talks on a radio while Yahya Abdul-Mateen II drives in Ambulance

Jake Gyllenhaal in Okja screaming

Mysterio in Spider-Man Far From Home

Lou Bloom looking out the window of his car while holding a camera in Nightcrawler Banner

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