| 100% | CASE | 4 | "The Curious ___ of Benjamin Button" (Brad Pitt movie) |
| 82% | CASE | 4 | "The Curious ___ of Benjamin Button," 2008 film directed by David Fincher starring Brad Pitt |
| 79% | BENJAMIN | 8 | The Curious Case of __ Button, film with Brad Pitt |
| 67% | BRAD | 4 | Pitt from "The Curious Case of Benjamin Button" |
| 63% | CASE | 4 | "The Curious ___ of Benjamin Button" |
| 62% | FIGHTCLUB | 9 | 1999 Brad Pitt movie hinted at by the beginnings of 17-, 21-, 39- and 52-Across |
| 62% | CASE | 4 | "The Curious ___ of Benjamin Button" (2008 film) |
| 61% | BUTTON | 6 | "The Curious Case of Benjamin ___" (Brad Pitt/Cate Blanchett film) |
| 58% | CATE | 4 | Brad's co-star in "The Curious Case of Benjamin Button" |
| 56% | BUTTON | 6 | The Curious Case of Benjamin __ |
| 54% | TREE | 4 | "The ___ of Life" (2011 Brad Pitt movie) |
| 53% | MONEYBALL | 9 | 2011 Brad Pitt movie about sports financing in the Major Leagues |
| 53% | TRISTAN | 7 | Brad Pitt played him in Legends of the Fall |
| 52% | ORMOND | 6 | Julia of "The Curious Case of Benjamin Button" |
| 51% | TROY | 4 | Brad Pitt movie loosely based on "The Iliad" |
| 50% | THETREEOFLIFE | 13 | Brad Pitt movie that won the top prize at the Cannes Film Festival in 2011: 4 wds. |
| 49% | PITT | 4 | "Benjamin Button" Brad of |
| 49% | ADASTRA | 7 | 2019 Brad Pitt sci-fi movie whose title means "to the stars" |
| 49% | TREE | 4 | Brad Pitt starrer "The ___ of Life" |
| 48% | MEET | 4 | "___ Joe Black," 1998 American fantasy film starring Brad Pitt as the angel of death |
| 48% | TROY | 4 | Brad Pitt movie |
| 47% | SEA | 3 | "By the ___" (2015 Brad Pitt movie) |
| 47% | ANGELINAJOLIE | 13 | She married Brad Pitt, her costar from the 2005 movie "Mr. & Mrs. Smith": 2 wds. |
| 47% | BENJAMIN | 8 | "The Curious Case of ___ Button" |
| 46% | OWN | 3 | "The Devil's ___" (1997 Brad Pitt movie) |
| 46% | FINCHER | 7 | David —, Best Director Oscar nominee for The Curious Case of Benjamin Button |
| 45% | FIGHTCLUB | 9 | 1999 Brad Pitt movie |
| 45% | BABEL | 5 | 2006 Brad Pitt movie |
| 45% | TROY | 4 | 2004 Brad Pitt movie |
| 45% | FIGHT | 5 | "___ Club," Brad Pitt movie |