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.

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26
Life is listed (or ranked) 26 on the list The Best Jake Gyllenhaal Movies
Jake Gyllenhaal, Rebecca Ferguson, Olga Dihovichnaya
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
27
Rendition is listed (or ranked) 27 on the list The Best Jake Gyllenhaal Movies
Reese Witherspoon, Meryl Streep, Jake Gyllenhaal
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
28
Demolition is listed (or ranked) 28 on the list The Best Jake Gyllenhaal Movies
Demolition
29
Highway is listed (or ranked) 29 on the list The Best Jake Gyllenhaal Movies
Jake Gyllenhaal, Jared Leto, Selma Blair
Highway is a 2002 American independent drama film written by Scott Rosenberg and directed by James Cox. It stars Jared Leto, Jake Gyllenhaal, and Selma Blair.
30
Moonlight Mile is listed (or ranked) 30 on the list The Best Jake Gyllenhaal Movies
Jake Gyllenhaal, Susan Sarandon, Dustin Hoffman
Moonlight Mile is a 2002 American romantic drama film written and directed by Brad Silberling. This film was loosely inspired by writer/director Brad Silberling's own experience. He was dating ...more
31
Lovely and Amazing is listed (or ranked) 31 on the list The Best Jake Gyllenhaal Movies
Jake Gyllenhaal, Emily Mortimer, Catherine Keener
Lovely and Amazing is a 2001 American comedy-drama film written and directed by Nicole Holofcener.
32
A Dangerous Woman is listed (or ranked) 32 on the list The Best Jake Gyllenhaal Movies
Jake Gyllenhaal, Maggie Gyllenhaal, Debra Winger
A Dangerous Woman is a 1993 film directed by Stephen Gyllenhaal. The screenplay was written by his then wife Naomi Foner, loosely based on the award winning novel of the same name by Mary ...more
33
Accidental Love is listed (or ranked) 33 on the list The Best Jake Gyllenhaal Movies
Jessica Biel, Jake Gyllenhaal, Kirstie Alley
Accidental Love is a 2015 American comedy film directed by David O. Russell and written by Russell, Kristin Gore, Matthew Silverstein and Dave Jeser, from the novel Sammy's Hill by Gore. The ...more