| 8.4 |  | Donnie Darko | 2001 | Drama Sci-Fi Thriller | Richard Kelly | Jake Gyllenhaal Jena Malone Mary McDonnell | * 3.8/5 |
| 8.0 | | Nightcrawler | 2014 | Crime Drama Thriller | Dan Gilroy | Jake Gyllenhaal Rene Russo Bill Paxton | * 3.9/5 |
| 8.0 | | End of Watch | 2012 | Action Crime Drama Drama Thriller | David Ayer | Jake Gyllenhaal Michael Pena Anna Kendrick | * 4.1/5 |
| 7.9 | | Zodiac | 2007 | Crime Drama Mystery Mystery Thriller | David Fincher | Jake Gyllenhaal Robert Downey Jr. Mark Ruffalo | * 3.6/5 |
| 7.3 | | Enemy | 2013 | Mystery Thriller Canada | Denis Villeneuve | Jake Gyllenhaal Melanie Laurent Sarah Gadon | * 2.7 /5 |
| 7.2 | | Stronger | 2017 | Biography Drama | David Gordon Green | Jake Gyllenhaal, Tatiana Maslany, Miranda Richardson | * 3.7/5 |
| 5.7 | | Velvet Buzzsaw | 2019 | Horror Mystery Thriller | Dan Gilroy | Jake Gyllenhaal Rene Russo Zawe Ashton | * 2.9 /5 |
| 8.3 | | Brokeback Mountain | 2005 | Drama Romance | Ang Lee | Jake Gyllenhaal Heath Ledger Michelle Williams | * 3.2/5 |
| 8.2 | | October Sky | 1999 | Biography Drama Family | Joe Johnston | Jake Gyllenhaal Chris Cooper Laura Dern | * 3.9/5 |
| 8.2 | | Prisoners | 2013 | Crime Drama Mystery Mystery Thriller | Denis Villeneuve | Hugh Jackman Jake Gyllenhaal Viola Davis | * 3.8/5 |
| 7.7 | | Source Code | 2011 | Action Drama Mystery Mystery Sci-Fi Thriller | Duncan Jones | Jake Gyllenhaal Michelle Monaghan Vera Farmiga | * 3.7/5 |
| 7.4 | | Brothers | 2009 | Action Drama Thriller Thriller War | Jim Sheridan | Jake Gyllenhaal Natalie Portman Tobey Maguire | * 3.6/5 |
| 7.1 | | Prince of Persia the Sands of Time | 2010 | Action Fantasy | Mike Newell | Jake Gyllenhaal Gemma Arterton Ben Kingsley | * 3.7/5 |
| 6.7 | | The Day After Tomorrow | 2004 | Action Adventure Sci-Fi Sci-Fi Thriller | Roland Emmerich | Dennis Quaid Jake Gyllenhaal Emmy Rossum | * 3.5/5 |
| 6.5 | | Highway | 2002 | Crime Drama | James Cox | Kimberley Kates Jared Leto Jake Gyllenhaal | * 3.1/5 |
| 7.8 | | I Am Heath Ledger | 2017 | Biography Documentary Canada | Derik Murray, Adrian Buitenhuis | Heath Ledger Ben Harper Kim Ledger | * 3.3/5 |
| 7.3 | | Everest | 2015 | Action Adventure Biography Biography Drama Thriller | Baltasar Kormákur | Jason Clarke Ang Phula Sherpa Thomas M. Wright | * 3.6/5 |
| 7.1 | v | Proof | 2005 | Drama Mystery | John Madden | Gwyneth Paltrow Anthony Hopkins Hope Davis | * 3.3/5 |
| 7.0 | | City Slickers | 1991 | Comedy | Ron Underwood | Billy Crystal Jack Palance Daniel Stern | * 3.5/5 |
| 7.0 | | City Slickers II the Legend of Curly s Gold | 1991 | Comedy | Ron Underwood | Billy Crystal Jack Palance Daniel Stern | |
| 7.9 | | Southpaw | 2015 | Drama Sport | Antoine Fuqua | Jake Gyllenhaal Rachel McAdams Oona Laurence | * 3.8/5 |
| 7.2 | | Moonlight Mile | 2002 | Drama Romance | Brad Silberling | Jake Gyllenhaal, Dustin Hoffman, Susan Sarandon | * 3.1/5 |
| 7.1 | | The Sisters Brothers | 2018 | Adventure Comedy Crime Crime Drama Western | Jacques Audiard | John C. Reilly Joaquin Phoenix Jake Gyllenhaal | * 2.9/5 |
| 8.4 | | Donnie Darko Director s Cut | 2001 | Drama Sci-Fi Thriller | Richard Kelly | Jake Gyllenhaal Jena Malone Mary McDonnell | * 3.9/5 |
| 6.2 | | Bubble Boy | 2001 | Adventure Comedy Romance Sci-Fi | Blair Hayes | Jake Gyllenhaal, Swoosie Kurtz, Marley Shelton | * 3.1/5 |
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