Entertainment

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.

list ordered by
1
Nightcrawler is listed (or ranked) 1 on the list The Best Jake Gyllenhaal Movies
teddybear1029 added Jake Gyllenhaal, Rene Russo, Bill Paxton
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
2
Prisoners is listed (or ranked) 2 on the list The Best Jake Gyllenhaal Movies
Hugh Jackman, Jake Gyllenhaal, Maria Bello
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
3
Zodiac is listed (or ranked) 3 on the list The Best Jake Gyllenhaal Movies
Robert Downey Jr., Jake Gyllenhaal, Mark Ruffalo
Zodiac is a 2007 American mystery-thriller film directed by David Fincher and based on Robert Graysmith's non-fiction book of the same name. Zodiac tells the story of the manhunt for a person ...more
4
Donnie Darko is listed (or ranked) 4 on the list The Best Jake Gyllenhaal Movies
Drew Barrymore, Ashley Tisdale, Jake Gyllenhaal
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
5
Brokeback Mountain is listed (or ranked) 5 on the list The Best Jake Gyllenhaal Movies
Anne Hathaway, Jake Gyllenhaal, Kate Mara
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
6
Source Code is listed (or ranked) 6 on the list The Best Jake Gyllenhaal Movies
Jake Gyllenhaal, Michelle Monaghan, Vera Farmiga
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
7
Southpaw is listed (or ranked) 7 on the list The Best Jake Gyllenhaal Movies
Harley Rae Reid added Rachel McAdams, Jake Gyllenhaal, Naomie Harris
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
8
End of Watch is listed (or ranked) 8 on the list The Best Jake Gyllenhaal Movies
Anna Kendrick, Jake Gyllenhaal, America Ferrera
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
9
Nocturnal Animals is listed (or ranked) 9 on the list The Best Jake Gyllenhaal Movies
Amy Adams, Jake Gyllenhaal, Michael Shannon
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
10
Enemy is listed (or ranked) 10 on the list The Best Jake Gyllenhaal Movies
vlad-vesa added Jake Gyllenhaal, Isabella Rossellini, Mélanie Laurent
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
11
Jarhead is listed (or ranked) 11 on the list The Best Jake Gyllenhaal Movies
Jake Gyllenhaal, Jamie Foxx, John Krasinski
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
12
Velvet Buzzsaw is listed (or ranked) 12 on the list The Best Jake Gyllenhaal Movies
Jake Gyllenhaal, Rene Russo, Zawe Ashton
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
13
The Day After Tomorrow is listed (or ranked) 13 on the list The Best Jake Gyllenhaal Movies
Emmy Rossum, Jake Gyllenhaal, Dennis Quaid
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
14
October Sky is listed (or ranked) 14 on the list The Best Jake Gyllenhaal Movies
Jake Gyllenhaal, Laura Dern, Chris Cooper
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
15
Spider-Man: Far From Home is listed (or ranked) 15 on the list The Best Jake Gyllenhaal Movies
Tom Holland, Samuel L. Jackson, Zendaya
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
16
Brothers is listed (or ranked) 16 on the list The Best Jake Gyllenhaal Movies
Natalie Portman, Jake Gyllenhaal, Carey Mulligan
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
17
Love & Other Drugs is listed (or ranked) 17 on the list The Best Jake Gyllenhaal Movies
Anne Hathaway, Jake Gyllenhaal, Jaimie Alexander
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
18
Prince of Persia: The Sands of... is listed (or ranked) 18 on the list The Best Jake Gyllenhaal Movies
Gemma Arterton, Jake Gyllenhaal, Ben Kingsley
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
19
The Good Girl is listed (or ranked) 19 on the list The Best Jake Gyllenhaal Movies
Jennifer Aniston, Zooey Deschanel, Jake Gyllenhaal
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.
20
Bubble Boy is listed (or ranked) 20 on the list The Best Jake Gyllenhaal Movies
Stacy Keibler, Jake Gyllenhaal, Zach Galifianakis
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
21
Everest is listed (or ranked) 21 on the list The Best Jake Gyllenhaal Movies
Erwin91 added jason clarke, jake gyllenhaal, josh brolin
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
22
Wildlife is listed (or ranked) 22 on the list The Best Jake Gyllenhaal Movies
Jake Gyllenhaal, Carey Mulligan, Ed Oxenbould
Wildlife is a 2018 American drama directed by Paul Dano. Set in 1960, a boy (Ed Oxenbould) watches his parents' (Carey Mulligan and Jake Gyllenhaal) marriage fall apart after they move to ...more
23
City Slickers is listed (or ranked) 23 on the list The Best Jake Gyllenhaal Movies
Jake Gyllenhaal, Billy Crystal, Danielle Harris
City Slickers is a 1991 American western comedy film directed by Ron Underwood and starring Billy Crystal, Daniel Stern, Bruno Kirby and Jack Palance, with supporting roles by Patricia Wettig, ...more
24
Demolition is listed (or ranked) 24 on the list The Best Jake Gyllenhaal Movies
Erwinnator91 added Jake Gyllenhaal, Naomi Watts, Chris Cooper
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
25
Proof is listed (or ranked) 25 on the list The Best Jake Gyllenhaal Movies
Gwyneth Paltrow, Jake Gyllenhaal, Anthony Hopkins
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