| 100% | COOLHANDLUKE | 12 | 1967 film with Paul Newman as a repeat escapee from a chain gang prison: 3 wds. |
| 40% | DEMOLITIONMAN | 13 | 1993 film with Wesley Snipes as a prison escapee who's frozen cryogenically until 2032: 2 wds. |
| 38% | WUSA | 4 | 1970 film with Paul Newman as a talk radio host |
| 38% | COOLHANDLUKE | 12 | 1967 Paul Newman prison drama title that includes the name of a body part: 3 wds. |
| 35% | GOINGINSTYLE | 12 | 2017 film with Morgan Freeman as a retiree who helps rob a bank: 3 wds. |
| 34% | THEHUSTLER | 10 | 1961 film, starring Paul Newman as a pool shark, that had a sequel 25 years later: 2 wds. |
| 33% | THEBUCKETLIST | 13 | 2007 film with Morgan Freeman as a terminally ill man on a wish-fulfilling trip: 3 wds. |
| 33% | DEAREVANHANSEN | 14 | 2021 Broadway film adaptation with Amy Adams as a grieving mom: 3 wds. |
| 33% | THEDIRTYDOZEN | 13 | 1967 film featuring Charles Bronson as an Army convict recruited into a WWII commando group: 3 wds. |
| 32% | ANOFFICERAND | 12 | With 41-Across, a film starring Richard Gere as an aspiring pilot, Zack Mayo: 3 wds. |
| 32% | ONTHEBEACH | 10 | 1959 film with Ava Gardner as one of the last survivors of a nuclear war: 3 wds. |
| 32% | THEPRIZE | 8 | 1963 spy film starring Paul Newman as a Nobelist |
| 32% | HUSTLER | 7 | The __, movie with Paul Newman as a pool player |
| 31% | NOBODYSFOOL | 11 | Novel by 28-Across adapted as a 1994 film starring Paul Newman (2 wds.) |
| 31% | THEGREENMILE | 12 | 1999 film starring Tom Hanks as a prison guard (3 wds.) |
| 30% | COOLHAND | 8 | __ Luke; 1967 prison film starring Paul Newman |
| 29% | AMERICANHUSTLE | 14 | 2013 crime film with Amy Adams as a con artist: 2 wds. |
| 29% | BATMANBEGINS | 12 | 2005 film with Morgan Freeman as a Wayne Enterprises employee: 2 wds. |
| 29% | ILLFLYAWAY | 10 | Gospel song with the lyric "Like a bird from these prison walls" (3 wds.) |
| 29% | NIGHTMAREALLEY | 14 | 2021 Guillermo del Toro film with Willem Dafoe as a carnival owner: 2 wds. |
| 28% | THEODDCOUPLE | 12 | 1968 film where Walter Matthau played a slob rooming with a neat freak: 3 wds. |
| 28% | PITCHPERFECT | 12 | 2012 film with Elizabeth Banks as a cappella competition judge Gail Abernathy-McKadden: 2 wds. |
| 28% | THEHUNGERGAMES | 14 | 2012 film with Elizabeth Banks as chaperone Effie Trinket: 3 wds. |
| 28% | FORTHEBOYS | 10 | 1991 film starring Bette Midler as a USO entertainer: 3 wds. |
| 28% | JULIEANDJULIA | 13 | 2009 movie with Amy Adams as a novice cook: 3 wds. |
| 28% | MYCOUSINVINNY | 13 | 1992 comedy with Joe Pesci as a New York lawyer handling an Alabama trial: 3 wds. |
| 28% | HUSTLER | 7 | With "The," Paul Newman film set in a pool hall |
| 28% | THETRUMANSHOW | 13 | 1998 Peter Weir film starring Jim Carrey as the unwitting star of a reality series: 3 wds. |
| 28% | THEWAYBACK | 10 | 2020 film starring Ben Affleck as a high school basketball coach: 3 wds. |
| 28% | THEBLUELAGOON | 13 | 1980 film starring 15-Across as a young castaway: 3 wds. |