| 100% | WALKING | 7 | "Dead Man ___," 1995 crime drama featuring Susan Sarandon and Sean Penn with an oxymoronic title |
| 32% | HEAT | 4 | 1995 crime drama with Al Pacino and Val Kilmer |
| 29% | MYSTICRIVER | 11 | 2003 crime drama film starring Sean Penn and Tim Robbins |
| 29% | STATEOFGRACE | 12 | 1990 crime drama film starring Sean Penn, Ed Harris and Gary Oldman |
| 28% | TRUELIES | 8 | Schwarzenegger movie with an oxymoronic title |
| 26% | TRUE | 4 | "___ Lies," 1994 action comedy starring Arnold Schwarzenegger with an oxymoronic title |
| 26% | RANGE | 5 | "At Close ___," crime drama film featuring Sean Penn as Bradford Whitewood Jr. which is based on a real life crime family |
| 26% | THEMOON | 7 | "Racing With ___," drama film featuring Sean Penn as Henry Nash whose title is also a Vaughn Monroe song: 2 wds. |
| 25% | FUTURE | 6 | "Back to the ___," 1985 sci-fi film starring Michael J. Fox with an oxymoronic title |
| 25% | IAMSAM | 6 | Sean Penn film with a Seussian title |
| 25% | WALKING | 7 | Dead Man __, Sean Penn is on death row |
| 25% | BRAVEHEART | 10 | 1995 epic historical drama featuring Mel Gibson and Patrick McGoohan, based on a poem titled "The Wallace" |
| 25% | THEUSUAL | 8 | & 22A 1995 crime drama film starring Stephen Baldwin and Gabriel Byrne |
| 24% | HEAT | 4 | 1995 crime drama starring Al Pacino and Val Kilmer |
| 24% | WIDE | 4 | "Eyes ___ Shut," 1999 drama starring Tom Cruise with an oxymoronic title |
| 24% | PEOPLE | 6 | Magazine with an annual "Sexiest Man Alive" feature |
| 24% | BETTERCALLSAUL | 14 | Crime drama set in Arizona and Nebraska that featured Carol Burnett in a recurring role as the mother of a con man (3 wds.) |
| 24% | FBI | 3 | CBS crime drama with Missy Peregrym and Zeeko Zaki |
| 24% | CARLITOS | 8 | & 12D 1993 crime drama film starring Al Pacino and Sean Penn |
| 23% | TWICE | 5 | "You Only Live ___," 1967 James Bond film starring Sean Connery with an oxymoronic title |
| 23% | JUSTCAUSE | 9 | 1995 film drama starring Sean Connery and Laurence Fishburne |
| 23% | USUALSUSPECTS | 13 | 1995 crime film for which Kevin Spacey won an Oscar, with "The": 2 wds. |
| 23% | NUN | 3 | Susan Sarandon in "Dead Man Walking" |
| 22% | KIN | 3 | 2018 sci-fi crime drama with Jack Reynor, Zoë Kravitz and James Franco |
| 22% | HEDGEMAZE | 9 | Garden feature with paths and dead ends: 2 wds. |
| 22% | IAMSAM | 6 | 2001 Sean Penn film whose title was inspired by "Green Eggs and Ham": 3 wds. |
| 21% | THEARTOFWAR | 11 | Classic work with chapters titled "Attack by Stratagem" and "Maneuvering an Army" |
| 21% | NINELIVES | 9 | 2005 film drama featuring Elpidia Carrillo and Robin Wright Penn |