| 100% | OWN | 3 | "The Devil's ___" (Brad Pitt movie) |
| 100% | OWN | 3 | "The Devil's ___" (1997 Brad Pitt movie) |
| 84% | MONEYBALL | 9 | 2011 Brad Pitt movie about sports financing in the Major Leagues |
| 80% | TROY | 4 | Brad Pitt movie loosely based on "The Iliad" |
| 80% | THETREEOFLIFE | 13 | Brad Pitt movie that won the top prize at the Cannes Film Festival in 2011: 4 wds. |
| 78% | FIGHTCLUB | 9 | 1999 Brad Pitt movie hinted at by the beginnings of 17-, 21-, 39- and 52-Across |
| 78% | PRADA | 5 | The devil's label, in a movie |
| 78% | ADASTRA | 7 | 2019 Brad Pitt sci-fi movie whose title means "to the stars" |
| 77% | SEA | 3 | "By the ___" (2015 Brad Pitt movie) |
| 77% | STARRER | 7 | "It's a Brad Pitt ___" (movie with Pitt as the lead) |
| 75% | TROY | 4 | Brad Pitt movie |
| 75% | ANGELINAJOLIE | 13 | She married Brad Pitt, her costar from the 2005 movie "Mr. & Mrs. Smith": 2 wds. |
| 73% | TREE | 4 | "The ___ of Life" (2011 Brad Pitt movie) |
| 72% | MONEYBALL | 9 | Brad Pitt manages the Oakland A's in this film |
| 72% | WAR | 3 | "World ___ Z" (2013 Brad Pitt movie) |
| 72% | WAR | 3 | "World ___ Z," 2013 Brad Pitt movie |
| 72% | FIGHTCLUB | 9 | 1999 Brad Pitt movie |
| 72% | BABEL | 5 | 2006 Brad Pitt movie |
| 72% | TROY | 4 | 2004 Brad Pitt movie |
| 72% | FIGHT | 5 | "___ Club," Brad Pitt movie |
| 72% | ADASTRA | 7 | 2019 Brad Pitt movie |
| 71% | ASTRA | 5 | "Ad ___" (2019 Brad Pitt movie) |
| 70% | MONEYBALL | 9 | Brad Pitt movie about assembling a baseball team |
| 67% | TROY | 4 | Brad Pitt's epic period war film loosely based on the decade-long Trojan War |
| 66% | BABEL | 5 | 2006 Brad Pitt movie named after a biblical tower |
| 66% | PRADA | 5 | The devil wears one in a movie |
| 65% | THETREEOFLIFE | 13 | 2011 Brad Pitt movie set in 1950s Texas: 4 wds. |
| 64% | TRISTAN | 7 | Brad Pitt played him in Legends of the Fall |
| 63% | WORLDWARZ | 9 | 2013 Brad Pitt zombie movie: 3 wds. |
| 63% | ASTRA | 5 | "Ad ___" (upcoming Brad Pitt sci-fi movie) |