By Megan Riedlinger
8:00pm PDT, Apr 22, 2023
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Jake Gyllenhaal got his turn as a comic book hero-turned-villain — and looked quite handsome doing it, might we add! — in 2019's "Spider-Man: Far from Home." The movie star tackled the role of Quentin Beck/Mysterio, a former Stark Industries employee who comes to the aid of Tom Holland's Spider-Man to help stop the Elementals — only he's not who Spidey thinks he is. The flick ended up being Jake's highest grossing film to date.
MORE: Marvel characters ranked
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Ever wondered what Jake Gyllenhaal would look like as a boxer? Fortunately, thanks to 2015's "Southpaw," we don't have to wonder anymore. Jake got into incredible shape for the role, which saw him playing professional boxer Billy "The Great" Hope.
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It isn't often that we get to see Jake Gyllenhaal as a romantic lead, which made 2010's "Love and Other Drugs" such a treat. He played womanizing pharma sales rep Jamie, who eventually falls for Anne Hathaway's character, Maggie, a patient in one of his trials. With a gaze like that, it's easy to see why Maggie liked him back.
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Jake Gyllenhaal polished up nicely (and rocked suspenders!) in 2015's "Demolition." The film gave us a glimpse of what Jake would look like as an investment banker.
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Love a man in uniform? Then you'll really appreciate Jake Gyllenhaal's turn in 2012's "End of Watch," an action thriller that saw him sport a shaved head as Officer Brian Taylor.
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Jake Gyllenhaal brought a video game to life in 2010's "Prince of Persia: The Sands Of Time." The film based on the "Prince of Persia" video game series saw Jake play Prince Dastan and treat fans to a look marked by armor, muscles and long hair.
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Who could resist those puppy dog eyes? Jake Gyllenhaal gave us a glimpse of their magic in the 2009 drama "Brothers." He starred as the brother of Tobey Maguire's character, a Marine whom he tries to help settle back into society after being held captive in Afghanistan.
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In 2005's "Brokeback Mountain," Jake Gyllenhaal played sheepherder Jack Twist in an unforgettable turn that saw him serve as one-half of a secret same-sex couple opposite Heath Ledger as cowboy Ennis Del Mar. Jake's performance in the film set in 1960s Wyoming earned him a best supporting actor nomination at the Academy Awards.
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A 24-year-old Jake Gyllenhaal starred opposite Gwyneth Paltrow in 2005's "Proof" — a film based on the Pulitzer Prize-winning play of the same name. Jake took on the role of former grad student Hal, who teams up with his former professor's daughter, Gwyneth's Catherine, to look for some of her late father's work. And he looked pretty convincing as a handsome University of Chicago alum.
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We almost couldn't see Jake Gyllenhaal's beautiful face in the action film "Everest." The actor rocked cold weather gear in the 2015 flick that chronicled the true story of the 1996 Mount Everest disaster. Jake played Scott Fischer, an American expedition leader who attempts to summit during the deadliest season ever to hit Mount Everest.
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Ladies who love glasses will need to check out 2019's "Velvet Buzzsaw." The film, in which Jake Gyllenhaal starred opposite Rene Russo, gave us a taste of what the actor would look like as an art critic — chunky spectacles included.
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Jake Gyllenhaal certainly cleaned up nicely in a suit and tie in 2011's "Source Code." The actor played Army Captain Colter Stevens in the thriller, which saw him investigating a terrorist bombing.
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Jake Gyllenhaal in space! We got to see exactly what that might look like thanks to the 2017 science fiction film "Life" in which he played Dr. David Jordan, a medical officer for the International Space Station during an expedition that uncovered life on Mars.
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If you want more cowboy Jake, well, Jake Gyllenhaal donned a big-brimmed hat in another Western in 2018: "The Sisters Brothers" saw the hunk playing John Morris, a private detectives in the 1800s.
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That perfectly coiffed 'do! Jake Gyllenhaal played Sam Hall in 2004's "The Day After Tomorrow," a disaster flick that saw him as the son of Dennis Quaid's character.
