| OTHERDRUGS | Romance starring Jake Gyllenhaal and Anne Hathaway, Love and ___ (5,5) |
| OTHER | Jake Gyllenhaal and Anne Hathaway romance, Love & ___ Drugs |
| DRUGS | Jake Gyllenhaal and Anne Hathaway romance, Love & Other _ |
| OCTOBERSKY | 1999 American biographical film directed by Joe Johnston, starring Jake Gyllenhaal and Chris Cooper |
| SOURCECODE | 2011 film thriller starring Jake Gyllenhaal and Michelle Monaghan (6,4) |
| LIFESAVERS | *Jake Gyllenhaal and Rebecca Ferguson in space...act frugally? |
| BRIGHTSTAR | 2009 period romance starring Abbie Cornish (6,4) |
| TENDERNESS | Michael Bolton "Time, Love & ___" |
| OCTOBER | 1999 film drama starring Jake Gyllenhaal and Chris Cooper (7,3) |
| DONNIE | 2001 film drama starring Jake Gyllenhaal and Jena Malone (6,5) |
| RENDITION | 2007 film thriller starring Jake Gyllenhaal and Reese Witherspoon (9) |
| 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 |
| DARKO | Donnie ___, 2001 film by Richard Kelly starring Jake Gyllenhaal and Jena Malone |
| DONNIEDARKO | 2001 film drama starring Jake Gyllenhaal and Jena Malone |
| 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) |
| ZODIAC | Crime drama starring Jake Gyllenhaal and Robert Downey Jr. (6) |
| PERSIA | Prince of _, 2010 film starring Jake Gyllenhaal and Gemma Arterton (6) |
