| 100% | MYSTIC | 6 | "___ River" (Sean Penn/Tim Robbins film) |
| 77% | MYSTICRIVER | 11 | 2003 crime drama film starring Sean Penn and Tim Robbins |
| 65% | MYSTICRIVER | 11 | Dennis Lehane novel made into a film starring Sean Penn and Tim Robbins (2 wds.) |
| 63% | MYSTICRIVER | 11 | 2003 movie set in Boston, for which Sean Penn and Tim Robbins each won a 1-Across: 2 wds. |
| 60% | MAN | 3 | "Dead ___ Walking" (1995 Sean Penn film) |
| 60% | RED | 3 | "The Thin __ Line"; Sean Penn film |
| 60% | IAMSAM | 6 | 2001 Sean Penn film |
| 59% | SHAWSHANK | 9 | Prison in 1994 Morgan Freeman and Tim Robbins film |
| 59% | IAMSAM | 6 | Sean Penn film with a Seussian title |
| 59% | PIZZA | 5 | “Licorice ___” (2021 Sean Penn film) |
| 57% | TREE | 4 | "The ___ of Life" (2011 Sean Penn film) |
| 57% | SAM | 3 | Sean Penn starrer drama film "I Am ___" |
| 55% | COLORS | 6 | 1988 Sean Penn police film directed by Dennis Hopper |
| 52% | ALLYSHEEDY | 10 | Actress who played Sean Penn's girlfriend in her '83 film debut |
| 51% | IAMSAM | 6 | 2001 Sean Penn/Dakota Fanning film: 3 wds. |
| 49% | IAMSAM | 6 | 2001 Sean Penn film whose title was inspired by "Green Eggs and Ham": 3 wds. |
| 49% | GREETINGSFROM | 13 | "___ Tim Buckley," 2012 film starring Penn Badgley as Jeff Buckley: 2 wds. |
| 48% | MYSTIC | 6 | "___ River" (2003 Sean Penn movie) |
| 44% | IAMSAM | 6 | 2001 film drama starring Sean Penn and Michelle Pfeiffer |
| 44% | UTURN | 5 | 1997 film thriller starring Sean Penn and Jennifer Lopez |
| 44% | ATCLOSERANGE | 12 | 1986 film drama starring Sean Penn and Christopher Walken |
| 42% | ANDY | 4 | Tim Robbins's "Shawshank Redemption" role |
| 42% | MADONNA | 7 | Sean Penn married her in 1985 |
| 42% | IAM | 3 | Sean Penn starrer "___ Sam": 2 wds. |
| 42% | IAM | 3 | Sean Penn's "___ Sam": 2 wds. |
| 42% | BOBROBERTS | 10 | 1992 Tim Robbins mockumentary |
| 42% | IAMSAM | 6 | 2001 Sean Penn movie |
| 42% | KWAI | 4 | Film river |
| 41% | EXES | 4 | Sean Penn and Guy Ritchie, to Madonna |