| DONNIEDARKO | 2001 film drama starring Jake Gyllenhaal and Jena Malone |
| DONNIE | 2001 film drama starring Jake Gyllenhaal and Jena Malone (6,5) |
| DARKO | Donnie ___, 2001 film by Richard Kelly starring Jake Gyllenhaal and Jena Malone |
| OCTOBER | 1999 film drama starring Jake Gyllenhaal and Chris Cooper (7,3) |
| MOONLIGHT | 2002 film drama starring Jake Gyllenhaal and Dustin Hoffman (9,4) |
| MOONLIGHTMILE | 2002 film drama starring Jake Gyllenhaal and Dustin Hoffman |
| SOUTHPAW | 2015 film drama starring Jake Gyllenhaal and Forest Whitaker |
| MILE | 2002 film drama starring Jake Gyllenhaal and Dustin Hoffman (4) |
| ZODIAC | Crime drama starring Jake Gyllenhaal and Robert Downey Jr. (6) |
| BROTHERS | 2009 drama starring Jake Gyllenhaal and Natalie Portman (8) |
| GOLDENEAGLE | Au pairs in Jena beat ugly English bird |
| OTHERDRUGS | Romance starring Jake Gyllenhaal and Anne Hathaway, Love and ___ (5,5) |
| RENDITION | 2007 film thriller starring Jake Gyllenhaal and Reese Witherspoon (9) |
| OCTOBERSKY | 1999 American biographical film directed by Joe Johnston, starring Jake Gyllenhaal and Chris Cooper |
| AMBULANCE | 2022 action thriller film starring Jake Gyllenhaal and Yahya Abdul-Mateen II (9) |
| BUBBLE | 2001 movie starring Jake Gyllenhaal and Swoosie Kurtz, - Boy (6) |
| SOURCECODE | 2011 film thriller starring Jake Gyllenhaal and Michelle Monaghan (6,4) |
| PERSIA | Prince of _, 2010 film starring Jake Gyllenhaal and Gemma Arterton (6) |
| JARHEAD | 2005 war film starring Jake Gyllenhaal and Peter Sarsgaard |
| BROKEBACKMOUNTAIN | Film starring Heath Ledger and Jake Gyllenhaal ... and a description of each set of circled letters |
