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The Best Jake Gyllenhaal Movies 

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Updated August 30, 2019 6k votes 1.2k voters 54.7k views 32 items

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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1
Donnie Darko is listed (or ranked) 1 on the list The Best Jake Gyllenhaal Movies
Drew Barrymore, Ashley Tisdale, Jake Gyllenhaal

Released: 2001

Directed by: Richard Kelly

Donnie Darko is a 2001 American supernatural drama film written and directed by Richard Kelly and starring Jake Gyllenhaal, Drew Barrymore, Patrick Swayze, Maggie Gyllenhaal, Noah Wyle, Jena ...more

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2
Prisoners is listed (or ranked) 2 on the list The Best Jake Gyllenhaal Movies
Hugh Jackman, Jake Gyllenhaal, Maria Bello

Released: 2013

Directed by: Denis Villeneuve

Prisoners is a 2013 American drama thriller film directed by Denis Villeneuve. Two young girls in Pennsylvania are kidnapped and the father of one of the girls, Keller Dover (Hugh Jackman), must ...more

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#25 of 240 The Best Psychological Thrillers of All Time #706 of 784 The Best Horror Movies Of All Time #68 of 134 The Best Movies You Never Want to Watch Again

3
Zodiac is listed (or ranked) 3 on the list The Best Jake Gyllenhaal Movies
Robert Downey Jr., Jake Gyllenhaal, Mark Ruffalo

Released: 2007

Directed by: David Fincher

Zodiac is a 2007 American mystery thriller film directed by David Fincher, based on the 1986 non-fiction book by Robert Graysmith. In the late 1960s/early 1970s, a San Francisco cartoonist (Jake ...more

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4
Nightcrawler is listed (or ranked) 4 on the list The Best Jake Gyllenhaal Movies
teddybear1029 added Jake Gyllenhaal, Rene Russo, Bill Paxton

Released: 2014

Directed by: Dan Gilroy

Nightcrawler is a 2014 American neo-noir thriller film written and directed by Dan Gilroy in his directorial debut. The film stars Jake Gyllenhaal who starts shooting footage in Los Angeles and ...more

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5
Brokeback Mountain is listed (or ranked) 5 on the list The Best Jake Gyllenhaal Movies
Anne Hathaway, Jake Gyllenhaal, Kate Mara

Released: 2005

Directed by: Ang Lee

Brokeback Mountain is a 2005 American epic romantic drama film directed by Ang Lee. It is a film adaptation of the 1997 short story of the same name by Annie Proulx; the screenplay was written ...more

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6
Source Code is listed (or ranked) 6 on the list The Best Jake Gyllenhaal Movies
Jake Gyllenhaal, Michelle Monaghan, Vera Farmiga

Released: 2011

Directed by: Duncan Jones

Source Code is a 2011 science fiction film directed by Duncan Jones, written by Ben Ripley, and starring Jake Gyllenhaal, Michelle Monaghan, Vera Farmiga, and Jeffrey Wright. The film had its ...more

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7
End of Watch is listed (or ranked) 7 on the list The Best Jake Gyllenhaal Movies
Anna Kendrick, Jake Gyllenhaal, America Ferrera

Released: 2012

Directed by: David Ayer

End of Watch is a 2012 American drama thriller film written and directed by David Ayer. It stars Jake Gyllenhaal and Michael Peña as Brian Taylor and Miguel Zavala, two Los Angeles Police ...more

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8
Southpaw is listed (or ranked) 8 on the list The Best Jake Gyllenhaal Movies
Harley Rae Reid added Rachel McAdams, Jake Gyllenhaal, Naomie Harris

Directed by: Antoine Fuqua

Southpaw is a 2015 American sports drama film directed by Antoine Fuqua. A champion boxer (Jake Gyllenhaal) fights to get his daughter back as well as revive his professional career, after an ...more

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9
Jarhead is listed (or ranked) 9 on the list The Best Jake Gyllenhaal Movies
Jake Gyllenhaal, Jamie Foxx, John Krasinski

Released: 2005

Directed by: Sam Mendes

Jarhead is a 2005 biographical drama film based on U.S. Marine Anthony Swofford's 2003 memoir of the same name, directed by Sam Mendes, starring Jake Gyllenhaal as Swofford with Jamie Foxx, ...more

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10
Enemy is listed (or ranked) 10 on the list The Best Jake Gyllenhaal Movies
vlad-vesa added Jake Gyllenhaal, Isabella Rossellini, Mélanie Laurent

Released: 2013

Directed by: Denis Villeneuve

Enemy is a 2013 Canadian-Spanish psychological thriller film directed by Denis Villeneuve, loosely adapted by Javier Gullón from José Saramago's 2002 novel The Double. The film ...more

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11
October Sky is listed (or ranked) 11 on the list The Best Jake Gyllenhaal Movies
Jake Gyllenhaal, Laura Dern, Chris Cooper

Released: 1999

Directed by: Joe Johnston

October Sky is a 1999 American biographical film directed by Joe Johnston, starring Jake Gyllenhaal, Chris Cooper and Laura Dern. It is based on the true story of Homer Hickam, a coal miner's ...more

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12
Spider-Man: Far From Hom... is listed (or ranked) 12 on the list The Best Jake Gyllenhaal Movies
Tom Holland, Samuel L. Jackson, Zendaya

Released: 2019

Directed by: Jon Watts

Spider-Man: Far From Home is a 2019 American superhero film directed by Jon Watts, based on the Marvel Comics character. While on a vacation trip to Europe with his friends, Peter Parker is ...more

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13
The Day After Tomorrow ... is listed (or ranked) 13 on the list The Best Jake Gyllenhaal Movies
Emmy Rossum, Jake Gyllenhaal, Dennis Quaid

Released: 2004

Directed by: Roland Emmerich

The Day After Tomorrow is a 2004 American climate fiction-disaster film co-written, directed, and produced by Roland Emmerich and starring Dennis Quaid, Jake Gyllenhaal, Ian Holm, Emmy Rossum, ...more

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14
Velvet Buzzsaw is listed (or ranked) 14 on the list The Best Jake Gyllenhaal Movies
Jake Gyllenhaal, Rene Russo, Zawe Ashton

Released: 2019

Directed by: Dan Gilroy

Velvet Buzzsaw is a 2019 American horror thriller film directed by Dan Gilroy. After a series of paintings by an unknown artist are discovered, a supernatural force enacts revenge on those who ...more

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15
Nocturnal Animals is listed (or ranked) 15 on the list The Best Jake Gyllenhaal Movies
Amy Adams, Jake Gyllenhaal, Michael Shannon

Released: 2016

Directed by: Tom Ford

Nocturnal Animals is a 2016 American neo-noir psychological thriller film directed by Tom Ford, based on the 1993 novel Tony and Susan by Austin Wright. A divorced art gallery owner (Amy Adams) ...more

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16
Love & Other Drugs ... is listed (or ranked) 16 on the list The Best Jake Gyllenhaal Movies
Anne Hathaway, Jake Gyllenhaal, Jaimie Alexander

Released: 2010

Directed by: Edward Zwick

Love & Other Drugs is a 2010 romantic comedy film written and directed by Edward Zwick and based on the non-fiction book Hard Sell: The Evolution of a Viagra Salesman by Jamie Reidy. The ...more

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17
Prince of Persia: The Sa... is listed (or ranked) 17 on the list The Best Jake Gyllenhaal Movies
Gemma Arterton, Jake Gyllenhaal, Ben Kingsley

Released: 2010

Directed by: Mike Newell

Prince of Persia: The Sands of Time is a 2010 American adventure action fantasy film written by Jordan Mechner, Boaz Yakin, Doug Miro, and Carlo Bernard; directed by Mike Newell; produced by ...more

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18
Brothers is listed (or ranked) 18 on the list The Best Jake Gyllenhaal Movies
Natalie Portman, Jake Gyllenhaal, Carey Mulligan

Released: 2009

Directed by: Jim Sheridan

Brothers is a 2009 American psychological drama war film directed by Jim Sheridan, and a remake of Susanne Bier's 2004 Danish film Brødre. Sam Cahill (Tobey Maguire) returns from being ...more

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19
The Good Girl is listed (or ranked) 19 on the list The Best Jake Gyllenhaal Movies
Jennifer Aniston, Zooey Deschanel, Jake Gyllenhaal

Released: 2002

Directed by: Miguel Arteta

The Good Girl is a 2002 comedy-drama film directed by Miguel Arteta from a script by Mike White, and stars Jennifer Aniston, Jake Gyllenhaal and John C. Reilly.

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20
Bubble Boy is listed (or ranked) 20 on the list The Best Jake Gyllenhaal Movies
Stacy Keibler, Jake Gyllenhaal, Zach Galifianakis

Released: 2001

Directed by: Blair Hayes

Bubble Boy is a 2001 comedy film directed by Blair Hayes and stars Jake Gyllenhaal in the title role, written by Cinco Paul and Ken Daurio. It was inspired by the 1976 movie The Boy in the ...more

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21
Demolition is listed (or ranked) 21 on the list The Best Jake Gyllenhaal Movies
Erwinnator91 added Jake Gyllenhaal, Naomi Watts, Chris Cooper

Released: 2016

Directed by: Jean-Marc Vallée

Demolition is a 2015 American drama film directed by Jean-Marc Vallée. A successful investment banker, Davis Mitchell (Jake Gyllenhaal), comes to terms with losing his wife in an ...more
22
Everest is listed (or ranked) 22 on the list The Best Jake Gyllenhaal Movies
Erwin91 added jason clarke, jake gyllenhaal, josh brolin

Released: 2015

Directed by: Doug Liman

Everest is a 2015 biographical adventure film directed by Baltasar Kormákur, based on the memoir by Beck Weathers. The story of New Zealand's Robert "Rob" Edwin Hall (Jason ...more

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23
Rendition is listed (or ranked) 23 on the list The Best Jake Gyllenhaal Movies
Reese Witherspoon, Meryl Streep, Jake Gyllenhaal

Released: 2007

Directed by: Gavin Hood

Rendition is a 2007 thriller film directed by Gavin Hood and starring Reese Witherspoon, Meryl Streep, Peter Sarsgaard, Alan Arkin, Jake Gyllenhaal and Omar Metwally. It centers on the ...more

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24
Proof is listed (or ranked) 24 on the list The Best Jake Gyllenhaal Movies
Gwyneth Paltrow, Jake Gyllenhaal, Anthony Hopkins

Released: 2005

Directed by: John Madden

Proof is a 2005 American drama film directed by John Madden and starring Gwyneth Paltrow, Anthony Hopkins, Jake Gyllenhaal, and Hope Davis. It was written by Rebecca Miller, based on David ...more

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25
Life is listed (or ranked) 25 on the list The Best Jake Gyllenhaal Movies
Jake Gyllenhaal, Rebecca Ferguson, Olga Dihovichnaya

Released: 2017

Directed by: Daniel Espinosa

Life is a 2017 science fiction horror thriller film directed by Daniel Espinosa. The film stars Jake Gyllenhaal, Rebecca Ferguson, Olga Dihovichnaya, Ariyon Bakare, Hiroyuki Sanada and Ryan ...more