| CRAZYHEART | 2009 Jeff Bridges music drama that costarred Maggie Gyllenhaal: 2 wds. |
| EMPIRE | Music drama that is allegedly based on "King Lear" |
| CSI | Longtime CBS drama that costarred Jorja Fox |
| CRAZY | 2009 film drama starring Jeff Bridges and Maggie Gyllenhaal |
| HEART | 2009 film drama starring Jeff Bridges and Maggie Gyllenhaal (5,5) |
| THEBIGLEBOWSKI | 1998 Jeff Bridges crime comedy that costarred John Goodman: 3 wds. |
| TOWERHEIST | 2011 Eddie Murphy caper film that costarred Ben Stiller: 2 wds. |
| TRADINGPLACES | 1983 Eddie Murphy comedy that costarred Dan Aykroyd: 2 wds. |
| THEUGLYTRUTH | 2009 Gerard Butler romantic comedy that costarred Katherine Heigl: 3 wds. |
| SEABISCUIT | 2003 Jeff Bridges horse-racing film that costarred Tobey Maquire |
| HORACEANDPETE | Web series set in a Brooklyn bar that costarred Edie Falco: 3 wds. |
| ANGELHASFALLEN | 2019 Gerard Butler action sequel that costarred Morgan Freeman: 3 wds. |
| DENOFTHIEVES | 2018 Gerard Butler heist film that costarred O'Shea Jackson Jr.: 3 wds. |
| THEPALEBLUEEYE | 2022 mystery thriller that costarred Gillian Anderson: 4 wds. |
| SECRETARY | 2002 comedy-drama film starring James Spader and Maggie Gyllenhaal (9) |
| STRANGERTHAN | and 8ac, 2006 comedy-drama film starring Will Ferrell and Maggie Gyllenhaal (8,4,7) |
| SARSGAARD | Peter ?, actor who married actress Maggie Gyllenhaal in 2009 (9) |
| LISASMILE | Julia Roberts and Maggie Gyllenhaal drama, Mona ... (4,5) |
| SISTER | What relation is Maggie Gyllenhaal to Jake Gyllenhaal? (6) |
| FICTION | and 8ac, 2006 comedy-drama film starring Will Ferrell and Maggie Gyllenhaal (8,4,7) |
