| 100% | OWN | 3 | "The Devil's ___" (1997 Brad Pitt movie) |
| 71% | OWN | 3 | "The Devil's ___" (Brad Pitt movie) |
| 69% | MONEYBALL | 9 | 2011 Brad Pitt movie about sports financing in the Major Leagues |
| 66% | STARRER | 7 | "It's a Brad Pitt ___" (movie with Pitt as the lead) |
| 65% | TROY | 4 | Brad Pitt movie loosely based on "The Iliad" |
| 65% | THETREEOFLIFE | 13 | Brad Pitt movie that won the top prize at the Cannes Film Festival in 2011: 4 wds. |
| 65% | TREE | 4 | "The ___ of Life" (2011 Brad Pitt movie) |
| 64% | FIGHTCLUB | 9 | 1999 Brad Pitt movie hinted at by the beginnings of 17-, 21-, 39- and 52-Across |
| 64% | PRADA | 5 | The devil's label, in a movie |
| 64% | ADASTRA | 7 | 2019 Brad Pitt sci-fi movie whose title means "to the stars" |
| 62% | OWN | 3 | "The Devil's ___," 1997 thriller movie starring Harrison Ford whose trailer was aired during Super Bowl XXXI |
| 62% | TROY | 4 | Brad Pitt movie |
| 61% | SEA | 3 | "By the ___" (2015 Brad Pitt movie) |
| 61% | ANGELINAJOLIE | 13 | She married Brad Pitt, her costar from the 2005 movie "Mr. & Mrs. Smith": 2 wds. |
| 59% | MONEYBALL | 9 | Brad Pitt manages the Oakland A's in this film |
| 59% | FIGHTCLUB | 9 | 1999 Brad Pitt movie |
| 59% | BABEL | 5 | 2006 Brad Pitt movie |
| 59% | TROY | 4 | 2004 Brad Pitt movie |
| 59% | FIGHT | 5 | "___ Club," Brad Pitt movie |
| 59% | ADASTRA | 7 | 2019 Brad Pitt movie |
| 58% | ASTRA | 5 | "Ad ___" (2019 Brad Pitt movie) |
| 57% | MONEYBALL | 9 | Brad Pitt movie about assembling a baseball team |
| 57% | WAR | 3 | "World ___ Z" (2013 Brad Pitt movie) |
| 57% | WAR | 3 | "World ___ Z," 2013 Brad Pitt movie |
| 55% | TROY | 4 | Brad Pitt's epic period war film loosely based on the decade-long Trojan War |
| 54% | BABEL | 5 | 2006 Brad Pitt movie named after a biblical tower |
| 54% | ASTRA | 5 | "Ad ___" (upcoming Brad Pitt sci-fi movie) |
| 53% | THETREEOFLIFE | 13 | 2011 Brad Pitt movie set in 1950s Texas: 4 wds. |
| 52% | SEA | 3 | "By the ___" (2015 movie starring Brad Pitt and Angelina Jolie) |
| 52% | TRISTAN | 7 | Brad Pitt played him in Legends of the Fall |