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The Best Jake Gyllenhaal Movies

Updated August 30, 2019 6.1k votes 1.3k voters 55.1k views32 items

List RulesVote 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.

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  • 1
    Prisoners
    344
    63

    Prisoners

    Hugh Jackman, Jake Gyllenhaal

    Released2013

    Directed byDenis Villeneuve

    Prisoners is a 2013 American drama thriller film directed by Denis Villeneuve. Two young girls... more on Wikipedia
  • 2
    Nightcrawler
    312
    41

    Nightcrawler

    Jake Gyllenhaal, Rene Russo

    Released2014

    Directed byDan Gilroy

    Nightcrawler is a 2014 American neo-noir thriller film written and directed by Dan Gilroy in... more on Wikipedia

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  • 3
    Donnie Darko
    360
    71

    Donnie Darko

    Drew Barrymore, Ashley Tisdale

    Released2001

    Directed byRichard Kelly

    Donnie Darko is a 2001 American supernatural drama film written and directed by Richard Kelly... more on Wikipedia
  • 4
    Zodiac
    267
    51

    Zodiac

    Robert Downey Jr., Jake Gyllenhaal

    Released2007

    Directed byDavid Fincher

    Zodiac is a 2007 American mystery thriller film directed by David Fincher, based on the 1986... more on Wikipedia
  • 5
    Southpaw
    187
    20

    Southpaw

    Rachel McAdams, Jake Gyllenhaal

    Directed byAntoine Fuqua

    Southpaw is a 2015 American sports drama film directed by Antoine Fuqua. A champion boxer... more on Wikipedia

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    #1567 of 1,647 The Most Rewatchable Movies#120 of 172 The Best Sports Movies Ever Made

  • 6
    Brokeback Mountain
    287
    81

    Brokeback Mountain

    Anne Hathaway, Jake Gyllenhaal

    Released2005

    Directed byAng Lee

    Brokeback Mountain is a 2005 American epic romantic drama film directed by Ang Lee. It is a... more on Wikipedia

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    #168 of 1,189 Every Oscar Winning Film Ever#36 of 160 The Most Utterly Depressing Movies Ever Made

  • 7
    Spider-Man: Far From Home
    237
    49

    Spider-Man: Far From Home

    Tom Holland, Samuel L. Jackson

    Released2019

    Directed byJon Watts

    Spider-Man: Far From Home is a 2019 American superhero film directed by Jon Watts, based on... more on Wikipedia

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  • 8
    End of Watch
    186
    33

    End of Watch

    Anna Kendrick, Jake Gyllenhaal

    Released2012

    Directed byDavid Ayer

    End of Watch is a 2012 American drama thriller film written and directed by David Ayer. It... more on Wikipedia

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  • 9
    Nocturnal Animals
    145
    12

    Nocturnal Animals

    Amy Adams, Jake Gyllenhaal

    Released2016

    Directed byTom Ford

    Nocturnal Animals is a 2016 American neo-noir psychological thriller film directed by Tom... more on Wikipedia

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    #117 of 242 The Best Psychological Thrillers of All Time#87 of 127 The Most Confusing Movies Ever Made

  • 10
    Enemy
    158
    23

    Enemy

    Jake Gyllenhaal, Isabella Rossellini

    Released2013

    Directed byDenis Villeneuve

    Enemy is a 2013 Canadian-Spanish psychological thriller film directed by Denis Villeneuve,... more on Wikipedia
  • 11
    Velvet Buzzsaw
    242
    49

    Velvet Buzzsaw

    Jake Gyllenhaal, Rene Russo

    Released2019

    Directed byDan Gilroy

    Velvet Buzzsaw is a 2019 American horror thriller film directed by Dan Gilroy. After a series... more on Wikipedia
  • 12
    Source Code
    228
    122

    Source Code

    Jake Gyllenhaal, Michelle Monaghan

    Released2011

    Directed byDuncan Jones

    Source Code is a 2011 science fiction film directed by Duncan Jones, written by Ben Ripley,... more on Wikipedia
  • 13
    The Day After Tomorrow
    161
    65

    The Day After Tomorrow

    Emmy Rossum, Jake Gyllenhaal

    Released2004

    Directed byRoland Emmerich

    The Day After Tomorrow is a 2004 American climate fiction-disaster film co-written, directed,... more on Wikipedia

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    #1 of 313 The Greatest Disaster Movies of All Time#50 of 165 Live Action Movies With The Best CGI Effects

  • 14
    Love & Other Drugs
    141
    37

    Love & Other Drugs

    Anne Hathaway, Jake Gyllenhaal

    Released2010

    Directed byEdward Zwick

    Love & Other Drugs is a 2010 romantic comedy film written and directed by Edward Zwick and... more on Wikipedia

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  • 15
    October Sky
    144
    71

    October Sky

    Jake Gyllenhaal, Laura Dern

    Released1999

    Directed byJoe Johnston

    October Sky is a 1999 American biographical film directed by Joe Johnston, starring Jake... more on Wikipedia

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    #20 of 84 Great Movies That Take Place in Autumn#33 of 236 The Best Movies Based On True Stories

  • 16
    Proof
    132
    25

    Proof

    Gwyneth Paltrow, Jake Gyllenhaal

    Released2005

    Directed byJohn Madden

    Proof is a 2005 American drama film directed by John Madden and starring Gwyneth Paltrow,... more on Wikipedia

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  • 17
    Jarhead
    151
    94

    Jarhead

    Jake Gyllenhaal, Jamie Foxx

    Released2005

    Directed bySam Mendes

    Jarhead is a 2005 biographical drama film based on U.S. Marine Anthony Swofford's 2003 memoir... more on Wikipedia

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    #2 of 10 The Best Movies About the Gulf War#136 of 374 The 50+ Best War Movies Ever Made, Ranked

  • 18
    Brothers
    129
    62

    Brothers

    Natalie Portman, Jake Gyllenhaal

    Released2009

    Directed byJim Sheridan

    Brothers is a 2009 American psychological drama war film directed by Jim Sheridan, and a... more on Wikipedia

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  • 19
    Bubble Boy
    74
    28

    Bubble Boy

    Stacy Keibler, Jake Gyllenhaal

    Released2001

    Directed byBlair Hayes

    Bubble Boy is a 2001 comedy film directed by Blair Hayes and stars Jake Gyllenhaal in the... more on Wikipedia

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  • 20
    Demolition
    78
    26

    Demolition

    Jake Gyllenhaal, Naomi Watts

    Released2016

    Directed byJean-Marc Vallée

    Demolition is a 2015 American drama film directed by Jean-Marc Vallée. A successful investment... more on Wikipedia
  • 21
    Prince of Persia: The Sands of Time
    120
    69

    Prince of Persia: The Sands of Time

    Gemma Arterton, Jake Gyllenhaal

    Released2010

    Directed byMike Newell

    Prince of Persia: The Sands of Time is a 2010 American adventure action fantasy film written... more on Wikipedia

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  • 22
    City Slickers
    128
    75

    City Slickers

    Jake Gyllenhaal, Billy Crystal

    Released1991

    Directed byRon Underwood

    City Slickers is a 1991 American western comedy film directed by Ron Underwood and starring... more on Wikipedia

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    #95 of 926 The All-Time Greatest Comedy Films#107 of 399 The Best Western Movies Ever Made

  • 23
    Everest
    57
    15

    Everest

    jason clarke, jake gyllenhaal

    Released2015

    Directed byDoug Liman

    Everest is a 2015 biographical adventure film directed by Baltasar Kormákur, based on the... more on Wikipedia
  • 24
    The Good Girl
    66
    24

    The Good Girl

    Jennifer Aniston, Zooey Deschanel

    Released2002

    Directed byMiguel Arteta

    The Good Girl is a 2002 comedy-drama film directed by Miguel Arteta from a script by Mike... more on Wikipedia

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    #29 of 31 The Best Cheating Wife Movies#8 of 50 The Best Good Movies

  • 25
    Wildlife
    17
    0

    Wildlife

    Jake Gyllenhaal, Carey Mulligan

    Released2018

    Directed byPaul Dano

    Wildlife is a 2018 American drama directed by Paul Dano. Set in 1960, a boy (Ed Oxenbould)... more on Wikipedia