| SHERRYBABY | 2006 film written and directed by Laurie Collyer starring Maggie Gyllenhaal in the title role (10) |
| DONNIE | Richard Kelly film starring Jake Gyllenhaal in the title role (6,5) |
| DARKO | Richard Kelly film starring Jake Gyllenhaal in the title role (6,5) |
| DONNIEDARKO | Cult 2001 film starring Jake Gyllenhaal in the title role |
| THEAPOSTLE | 1997 film written and directed by Robert Duvall, who also stars in the title role |
| CRAZYHEART | 2009 film drama starring Jeff Bridges and Maggie Gyllenhaal |
| SCHOOLDAZE | 1988 comedy-drama film written and directed by Spike Lee (6,4) |
| THEWARGAME | 1965 film written and directed by Peter Watkins that won a Best Documentary Academy Award |
| PASSEDAWAY | 1992 film written and directed by Charlie Peters (6,4) |
| MEDIUMCOOL | 1969 film written and directed by Haskell Wexler (6,4) |
| SOURGRAPES | 1998 comedy film written and directed by Larry David |
| KATIEHOLMES | Actress whose Batman Begins role was recast with Maggie Gyllenhaal in its 2008 sequal: 2 ds. |
| SARSGAARD | Peter ?, actor who married actress Maggie Gyllenhaal in 2009 (9) |
| LADY | The - in the Van; starring Maggie Smith, a film adaptation of an original play Alan Bennett based on |
| CIDER | Drink in the title of books by Laurie Lee and John Irving |
| STRANGERTHAN | 2006 comedy-drama film starring Will Ferrell and Maggie Gyllenhaal (8,4,7) |
| FICTION | 2006 comedy-drama film starring Will Ferrell and Maggie Gyllenhaal (8,4,7) |
| WILLPENNY | Film written and directed by Tom Gries starring Charlton Heston in the title role (4,5) |
| WAITRESS | 2007 film written and directed by Adrienne Shelly starring Keri Russell in the title role (8) |
| VAN | The Lady in the -, 2015 comedy-drama him starring Maggie Smith (3) |
