The Best Jake Gyllenhaal Movies

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List Criteria: 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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  1. 1
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    Prisoners is listed (or ranked) 1 on the list The Best Jake Gyllenhaal Movies


    Hugh Jackman, Jake Gyllenhaal, Maria Bello

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  2. 2
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    Donnie Darko is listed (or ranked) 2 on the list The Best Jake Gyllenhaal Movies


    Drew Barrymore, Ashley Tisdale, Jake Gyllenhaal

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    Zodiac is listed (or ranked) 3 on the list The Best Jake Gyllenhaal Movies

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    Robert Downey Jr., Jake Gyllenhaal, Mark Ruffalo

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  4. 4
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    Brokeback Mountain is listed (or ranked) 4 on the list The Best Jake Gyllenhaal Movies


    Anne Hathaway, Jake Gyllenhaal, Kate Mara

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  5. 5
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    Source Code is listed (or ranked) 5 on the list The Best Jake Gyllenhaal Movies


    Jake Gyllenhaal, Michelle Monaghan, Vera Farmiga

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  6. 6
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    End of Watch is listed (or ranked) 6 on the list The Best Jake Gyllenhaal Movies


    Anna Kendrick, Jake Gyllenhaal, America Ferrera

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  7. 7
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    Jarhead is listed (or ranked) 7 on the list The Best Jake Gyllenhaal Movies


    Jake Gyllenhaal, Jamie Foxx, John Krasinski

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  8. 8
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    The Day After Tomorrow is listed (or ranked) 8 on the list The Best Jake Gyllenhaal Movies


    Emmy Rossum, Jake Gyllenhaal, Dennis Quaid

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    Jake Gyllenhaal, Rene Russo, Bill Paxton

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  10. 10
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    October Sky is listed (or ranked) 10 on the list The Best Jake Gyllenhaal Movies


    Jake Gyllenhaal, Laura Dern, Chris Cooper

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  11. 11
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    Brothers is listed (or ranked) 11 on the list The Best Jake Gyllenhaal Movies


    Natalie Portman, Jake Gyllenhaal, Carey Mulligan

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  12. 12
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    Love & Other Drugs is listed (or ranked) 12 on the list The Best Jake Gyllenhaal Movies


    Anne Hathaway, Jake Gyllenhaal, Jaimie Alexander

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    Southpaw is listed (or ranked) 13 on the list The Best Jake Gyllenhaal Movies

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    Rachel McAdams, Jake Gyllenhaal, Naomie Harris

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  14. 14
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    The Good Girl is listed (or ranked) 14 on the list The Best Jake Gyllenhaal Movies


    Jennifer Aniston, Zooey Deschanel, Jake Gyllenhaal

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  15. 15
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    Prince of Persia: The Sands of... is listed (or ranked) 15 on the list The Best Jake Gyllenhaal Movies


    Gemma Arterton, Jake Gyllenhaal, Ben Kingsley

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    ENEMY is listed (or ranked) 16 on the list The Best Jake Gyllenhaal Movies

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    Jake Gyllenhaal, Isabella Rossellini, Mélanie Laurent

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  17. 17
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    Proof is listed (or ranked) 17 on the list The Best Jake Gyllenhaal Movies


    Gwyneth Paltrow, Jake Gyllenhaal, Anthony Hopkins

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  18. 18
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    City Slickers is listed (or ranked) 18 on the list The Best Jake Gyllenhaal Movies


    Jake Gyllenhaal, Billy Crystal, Danielle Harris

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  19. 19
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    Bubble Boy is listed (or ranked) 19 on the list The Best Jake Gyllenhaal Movies


    Stacy Keibler, Jake Gyllenhaal, Zach Galifianakis

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    Rendition is listed (or ranked) 20 on the list The Best Jake Gyllenhaal Movies


    Reese Witherspoon, Meryl Streep, Jake Gyllenhaal

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    Highway is listed (or ranked) 21 on the list The Best Jake Gyllenhaal Movies


    Jake Gyllenhaal, Jared Leto, Selma Blair

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    Moonlight Mile is listed (or ranked) 22 on the list The Best Jake Gyllenhaal Movies


    Jake Gyllenhaal, Susan Sarandon, Dustin Hoffman

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    jason clarke, jake gyllenhaal, josh brolin

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  24. 24
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    Lovely and Amazing is listed (or ranked) 24 on the list The Best Jake Gyllenhaal Movies


    Jake Gyllenhaal, Emily Mortimer, Catherine Keener

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    A Dangerous Woman is listed (or ranked) 25 on the list The Best Jake Gyllenhaal Movies


    Jake Gyllenhaal, Maggie Gyllenhaal, Debra Winger

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    The Man Who Walked Between the... is listed (or ranked) 26 on the list The Best Jake Gyllenhaal Movies


    The Man Who Walked Between the Towers Jake Gyllenhaal

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    Accidental Love is listed (or ranked) 27 on the list The Best Jake Gyllenhaal Movies


    Jessica Biel, Jake Gyllenhaal, Kirstie Alley

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