| 100% | THELEGENDOF | 11 | With 36-Across, 2000 golf film starring Will Smith and Matt Damon: 3 wds. |
| 49% | BOUGHTAZOO | 10 | "We ___," a 2011 film starring Matt Damon and Scarlett Johansson - whose birthday it is today: 3 wds. |
| 42% | THEEDGEOF | 9 | With 36-Across, 2016 coming-of-age film starring Hailee Steinfeld: 3 wds. |
| 40% | DOGMA | 5 | Kevin Smith film starring Ben Affleck and Matt Damon |
| 39% | DOGMA | 5 | 1999 Kevin Smith film starring Ben Affleck and Matt Damon |
| 38% | WEBOUGHTAZOO | 12 | 2011 Cameron Crowe film starring Matt Damon and Scarlett Johansson: 4 wds. |
| 37% | IAMLEGEND | 9 | Post-apocalyptic thriller starring Will Smith and his daughter Willow Smith (3 wds.) |
| 37% | IRRBBT | 6 | 2004 action film starring Will Smith and Bridget Moynahan |
| 37% | IROBOT | 6 | 2004 action film starring Will Smith and Bridget Moynahan |
| 37% | MARTIAN | 7 | "The ___," 2015 sci-fi film starring Matt Damon that was made with NASA collaboration |
| 37% | IAMLEGEND | 9 | 2007 sci-fi film starring Will Smith and Alice Braga |
| 37% | MEN | 3 | "___ in Black," film starring Will Smith and Tommy Lee Jones |
| 37% | SUICIDE | 7 | "___ Squad," 2016 superhero film starring Will Smith and Margot Robbie |
| 37% | FOCUS | 5 | 2015 comedy-drama film starring Will Smith and Margot Robbie |
| 36% | IAM | 3 | "___ Legend," 2007 film starring Will Smith: 2 wds. |
| 35% | BATTLEOF | 8 | With 36-Across, 2017 sports film starring Emma Stone as Billie Jean King (2 wds.) |
| 35% | WORDSPRONOUNCED | 15 | With 36- and 58-Across, what the answers to the starred clues are |
| 35% | SHESALLTHAT | 11 | Teen romantic comedy film starring Paul Walker which is a modern adaptation of "My Fair Lady" and "Pygmalion": 3 wds. |
| 35% | SUICIDE | 7 | & 16A 2016 action film starring Will Smith, Jared Leto and Margot Robbie |
| 35% | THERAINMAKER | 12 | 1997 legal drama film starring Matt Damon which is based on John Grisham's novel of the same name: 2 wds. |
| 34% | CADDYSHACK | 10 | 1980 golf film starring 18-Across, 31-Across, and Bill Murray as an unusual groundskeeper (2 wds.) |
| 34% | IAM | 3 | "___ Legend," 2007 post-apocalyptic film starring Will Smith which is about a pandemic: 2 wds. |
| 34% | BLADESOFGLORY | 13 | Sports comedy film starring Will Ferrell and Jon Heder as Olympic ice skaters (3 wds.) |
| 34% | BLADESOFGLORY | 13 | Sports comedy film starring Will Ferrell and Jon Heder as professional ice skaters (3 wds.) |
| 32% | GRIT | 4 | "True ___," a film starring Matt Damon and Jeff Bridges |
| 32% | MARTIAN | 7 | 2015 sci-fi film starring Matt Damon, with "The" |
| 32% | GREEN | 5 | 2010 action film starring Matt Damon and Greg Kinnear |
| 32% | UNFROSTED | 9 | 2024 film starring Melissa McCarthy, 15-Across, and 30-Across with the tagline "A Pop-Tart Will Rise" |