film The Best Jake Gyllenhaal Movies

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List Rules Vote for your favorite movies, regardless of critic reviews or how big the role was.

This is a list of the best Jake Gyllenhaal movies, ranked best to worst - with movie trailers when available. Jake Gyllenhaal's first role was in the 1991 film City Slickers alongside Billy Crystal and Daniel Stern. Jake Gyllenhaal's highest grossing movies have received a lot of accolades over the years, earning millions upon millions around the world. The order of these top Jake Gyllenhaal movies is decided by how many votes they receive, so only highly rated Jake Gyllenhaal movies will be at the top of the list. 

This list answers the questions, "What are the best Jake Gyllenhaal movies?," "What are the greatest Jake Gyllenhaal roles of all time?," and "How do Gyllenhaal's recent films compare with his first?" The greatest Jake Gyllenhaal performances didn't necessarily come from the best movies, but in most cases they go hand in hand. Famous flicks like Donnie Darko and Zodiac. appear on this Jake Gyllenhaal filmography, but it's up to fans like you to decide upon the best. If you think the best Jake Gyllenhaal role isn't at the top, then upvote it so it has the chance to become number one. 

If you are a fan of Gyllenhaal's dark performances, you might also enjoy our list of best Robert Downey, Jr. movies and best Heath Ledger movies.

If you're a fan of Jake Gyllenhaal, then check out our lists of the best Josh Brolin and Andrew Dice Clay movies as well.

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Nightcrawler Jake Gyllenhaal, Rene Russo, Bill Paxton

The Best Frank Sinatra Songs of All Time The Best Superhero Toy Lines

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Prisoners Hugh Jackman, Jake Gyllenhaal, Maria Bello

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Donnie Darko Drew Barrymore, Ashley Tisdale, Jake Gyllenhaal

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Zodiac Robert Downey Jr., Jake Gyllenhaal, Mark Ruffalo

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Brokeback Mountain Anne Hathaway, Jake Gyllenhaal, Kate Mara

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Source Code Jake Gyllenhaal, Michelle Monaghan, Vera Farmiga

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Southpaw Rachel McAdams, Jake Gyllenhaal, Naomie Harris

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End of Watch Anna Kendrick, Jake Gyllenhaal, America Ferrera

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Jarhead Jake Gyllenhaal, Jamie Foxx, John Krasinski

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The Day After Tomorrow Emmy Rossum, Jake Gyllenhaal, Dennis Quaid

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ENEMY Jake Gyllenhaal, Isabella Rossellini, Mélanie Laurent

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October Sky Jake Gyllenhaal, Laura Dern, Chris Cooper

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Love & Other Drugs Anne Hathaway, Jake Gyllenhaal, Jaimie Alexander

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Nocturnal Animals is listed (or ranked) 14 on the list The Best Jake Gyllenhaal Movies
Nocturnal Animals Jake Gyllenhaal, Aaron Taylor-Johnson, Amy Adams

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Brothers Natalie Portman, Jake Gyllenhaal, Carey Mulligan

Jake Gyllenhaal's Loves & Hookups The Best Movies That Were Originally Panned by Critics

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The Good Girl Jennifer Aniston, Zooey Deschanel, Jake Gyllenhaal

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Prince of Persia: The Sands of Time Gemma Arterton, Jake Gyllenhaal, Ben Kingsley

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Demolition is listed (or ranked) 18 on the list The Best Jake Gyllenhaal Movies

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Proof Gwyneth Paltrow, Jake Gyllenhaal, Anthony Hopkins

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Bubble Boy Stacy Keibler, Jake Gyllenhaal, Zach Galifianakis

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City Slickers Jake Gyllenhaal, Billy Crystal, Danielle Harris

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Everest is listed (or ranked) 22 on the list The Best Jake Gyllenhaal Movies
Everest jason clarke, jake gyllenhaal, josh brolin

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Rendition Reese Witherspoon, Meryl Streep, Jake Gyllenhaal

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Moonlight Mile Jake Gyllenhaal, Susan Sarandon, Dustin Hoffman

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Highway Jake Gyllenhaal, Jared Leto, Selma Blair

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Lovely and Amazing Jake Gyllenhaal, Emily Mortimer, Catherine Keener

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A Dangerous Woman Jake Gyllenhaal, Maggie Gyllenhaal, Debra Winger

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Life Jake Gyllenhaal, Rebecca Ferguson, Olga Dihovichnaya

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Accidental Love Jessica Biel, Jake Gyllenhaal, Kirstie Alley