| 100% | THEDEPARTED | 11 | Leonardo DiCaprio movie also starring Jack Nicholson and Matt Damon: 2 wds |
| 58% | SHUTTERISLAND | 13 | A Leonardo DiCaprio movie also starring Mark Ruffalo and Ben Kingsley: 2 wds |
| 53% | THEREVENANT | 11 | A Leonardo DiCaprio movie also starring Tom Hardy: 2 wds |
| 48% | DEPARTED | 8 | "The ___," 2006 crime film starring Jack Nicholson and Matt Damon |
| 46% | AFEW | 4 | "___ Good Men," 1992 movie starring Jack Nicholson and Tom Cruise: 2 wds. |
| 41% | THEDEPARTED | 11 | 2006 Scorsese movie starring 15-Across and Leonardo DiCaprio: 2 wds. |
| 40% | AFEW | 4 | "___ Good Men," movie starring Tom Cruise and Jack Nicholson: 2 wds. |
| 39% | THESHINING | 10 | 1980 Jack Nicholson horror movie featuring Bartók's "Music for Strings, Percussion, and Celesta": 2 wds. |
| 36% | THEAVIATOR | 10 | 2004 Martin Scorsese movie starring Leonardo DiCaprio: 2 wds. |
| 36% | SHUTTERISLAND | 13 | 2010 Martin Scorsese movie starring Leonardo DiCaprio: 2 wds. |
| 35% | FIVEEASYPIECES | 14 | "Odd" 1970 film starring Jack Nicholson and Karen Black: 3 wds. |
| 35% | AZOO | 4 | "We Bought ___" (2011 Matt Damon movie): 2 wds. |
| 35% | AFEW | 4 | "___ Good Men" starring Tom Cruise and Jack Nicholson: 2 wds. |
| 34% | ASGOODASITGETS | 14 | 1997 Oscar-winning romantic dramedy starring Jack Nicholson and Helen Hunt (2 wds.) |
| 34% | SHUTTERISLAND | 13 | 2010 Leonardo DiCaprio movie set at a Boston psychiatric hospital: 2 wds. |
| 33% | TOMHARDY | 8 | Leonardo DiCaprio's "The Revenant" co-star who also starred in 15-Across, 19-Across, 28-Across, and 42-Across (2 wds.) |
| 33% | FREAKDANCE | 10 | 2011 comedy starring Amy Poehler and Matt Besser: 2 wds. |
| 32% | IRONWEED | 8 | 1987 drama starring Jack Nicholson and Meryl Streep |
| 32% | CHINATOWN | 9 | 1974 drama starring Jack Nicholson and Faye Dunaway |
| 32% | MARSATTACKS | 11 | 1996 comedy starring Jack Nicholson and Glenn Close |
| 32% | GREENZONE | 9 | 2010 Matt Damon movie based on the nonfiction book "Imperial Life in the Emerald City": 2 wds. |
| 31% | WOLF | 4 | 1994 film drama starring Jack Nicholson and Michelle Pfeiffer |
| 31% | IRONWEED | 8 | 1987 film drama starring Jack Nicholson and Meryl Streep |
| 31% | THEBORDER | 9 | 1982 film drama starring Jack Nicholson and Harvey Keitel |
| 31% | THECROSSING | 11 | 1995 film drama starring Jack Nicholson and David Morse |
| 31% | CROSSING | 8 | The —, 1995 drama starring Jack Nicholson and David Morse |
| 31% | BOUGHTAZOO | 10 | "We ___," 2011 family-drama movie starring Matt Damon and Scarlett Johansson: 3 wds. |
| 31% | LASTDETAIL | 10 | The —, 1973 comedy-drama starring Jack Nicholson and Otis Young |