| 100% | EXES | 4 | Jennifer Aniston and Brad Pitt, vis-à-vis each other |
| 48% | ONCE | 4 | "___ Upon a Time in Hollywood" (movie that Brad Pitt and Leonardo DiCaprio each earned $10 million for) |
| 41% | THELMA | 6 | __ and Louise, feminist film with a young Brad Pitt |
| 39% | IDO | 3 | Words a bride and groom say to each other: 2 wds. |
| 38% | ONCE | 4 | "___ Upon a Time in Hollywood," movie starring Brad Pitt and Margot Robbie |
| 38% | MONEYBALL | 9 | Analytics-based sports philosophy, and the name of a Brad Pitt film |
| 38% | IDO | 3 | Words that a bride and groom say to each other: 2 wds. |
| 38% | SHOW | 4 | "The Morning ___," series about a breakfast news program, starring Jennifer Aniston and Reese Witherspoon on Apple TV+ |
| 38% | MORNING | 7 | "The ___ Show," TV series starring Jennifer Aniston and Steve Carell that is about a fictional news show |
| 38% | TROY | 4 | A greek epic which was made into a film starring Brad Pitt and Orlando Bloom |
| 37% | IDO | 3 | What a bride and groom say to each other at the altar: 2 wds. |
| 37% | ONCE | 4 | "___ Upon a Time in Hollywood," 2019 comedy drama film starring Brad Pitt and Margot Robbie |
| 34% | HOLLYWOOD | 9 | "Once Upon a Time in ___," 2019 comedy-drama film starring Brad Pitt and Leonardo DiCaprio about Hollywood's "golden age" |
| 34% | EXES | 4 | Angelina Jolie and Brad Pitt, for example |
| 34% | SEXSYMBOLS | 10 | Angelina Jolie and Brad Pitt, e.g. |
| 34% | SHILOH | 6 | Daughter of Angelina Jolie and Brad Pitt |
| 33% | FIGHTCLUB | 9 | 1996 novel by Chuck Palahniuk featuring an unnamed protagonist, with a film adaptation starring Brad Pitt and Edward Norton: 2 wds. |
| 33% | ORS | 3 | Tom Cruise and Brad Pitt are famous act___ |
| 33% | CLUB | 4 | "Fight ___," movie starring Edward Norton and Brad Pitt |
| 33% | PUNCTUATIONMARK | 15 | What ends many a line, and what begins each of the puzzle's three other long answers |
| 33% | HES | 3 | "___ Just Not That into You," a 2009 romantic comedy featuring an ensemble cast with the likes of Ben Affleck and Jennifer Aniston |
| 33% | JESSEJAMES | 10 | Film title role for Tyrone Power and Brad Pitt |
| 33% | FIGHT | 5 | "___ Club," 1999 movie starring Edward Norton and Brad Pitt |
| 33% | TROY | 4 | Eric Bana and Brad Pitt starrer historical drama film |
| 33% | OKLAHOMA | 8 | State where Dr. Phil and Brad Pitt are from |
| 33% | SPYGAME | 7 | 2001 action film starring Robert Redford and Brad Pitt |
| 33% | FIGHTCLUB | 9 | 1999 film with Brad Pitt as a soap salesman |
| 32% | ARTICLES | 8 | A and others |
| 32% | LOOSELEAF | 9 | Kind of paper ... and a hint to a sequence, each starting with a different letter, found in four other puzzle answers |