| 100% | MYCOUSINVINNY | 13 | 1992 courtroom comedy for which 18-Across won an Academy Award: 3 wds. |
| 52% | THEWRESTLER | 11 | 2008 sports drama for which 18-Across was nominated for an Academy Award: 2 wds. |
| 45% | STILLALICE | 10 | 2014 film for which 30-Across recently won an Academy Award for Best Actress: 2 wds. |
| 41% | THEGRADUATE | 11 | 1967 film for which 18-Across won his Best Director Oscar: 2 wds. |
| 37% | BESTACTOR | 9 | Academy Award category in which 15-Across received a nomination for 36-Across: 2 wds. |
| 36% | ALLABOUTSTEVE | 13 | 2009 film for which 34-Across won a Razzie for Worst Actress: 3 wds. |
| 36% | GAMECHANGE | 10 | 2012 HBO movie for which 30-Across won an Emmy for portraying Sarah Palin: 2 wds. |
| 34% | PRETTYWOMAN | 11 | 1990 romantic comedy for which Julia Roberts was nominated for an Oscar: 2 wds. |
| 34% | BLACKSWAN | 9 | Film for which Natalie Portman won an Oscar: 2 wds. |
| 34% | HANNAH | 6 | "Girls" role for which 18-Across won a Best Actress Golden Globe |
| 33% | POSTMALONE | 10 | 18-Across, 27-Across, and 34-Across rapper/singer who won the 2025 American Music Award for Favorite Country Male Artist (2 wds.) |
| 33% | SUPERBOWLXLIV | 13 | 2009 game in which 15-Across won the MVP award: 3 wds. |
| 33% | NORMARAE | 8 | 1979 movie for which Sally Field won an Oscar: 2 wds. |
| 33% | WESTSIDESTORY | 13 | Movie for which 59-Across won an Oscar, 1961 |
| 32% | THEMUPPETSHOW | 13 | TV program for which 59-Across won an Emmy, 1977 |
| 31% | BLINDSIDE | 9 | With "The," 2009 film for which 34-Across won an Oscar: 2 wds. |
| 31% | ASINGLEMAN | 10 | 2009 drama for which 21-Across was nominated for an Oscar: 3 wds. |
| 31% | WESTSIDESTORY | 13 | 1961 Bernstein/Sondheim musical that won 10 Academy Awards: 3 wds. |
| 31% | THEBRADYBUNCH | 13 | Classic sitcom in which 18-Across played a housekeeper: 3 wds. |
| 31% | USUALSUSPECTS | 13 | 1995 crime film for which Kevin Spacey won an Oscar, with "The": 2 wds. |
| 31% | THEWESTWING | 11 | 1999-2006 drama for which 30-Across won four Emmys: 3 wds. |
| 31% | SIDNEYPOITIER | 13 | First black person to win the Academy Award for Best Actor: 2 wds. |
| 30% | BESTACTRESS | 11 | Oscar that 32-Across won for 18-Across: 2 wds. |
| 29% | LILIESOF | 8 | With 64-Across, film for which 47-Across won an Oscar for Best Actor |
| 29% | ADELE | 5 | Singer of the first James Bond movie theme song ever to win an Academy Award |
| 29% | PULITZERPRIZE | 13 | Fiction award won by 18-/42-Across in 2015: 2 wds. |
| 28% | VITOCORLEONE | 12 | Academy Award-winning role for both 20- and 26-Across |
| 28% | SHAMPOO | 7 | Movie for which Lee Grant won an Oscar |
| 28% | KLUTE | 5 | Movie for which Jane Fonda won an Oscar |
| 28% | MARTY | 5 | Movie for which Ernest Borgnine won an Oscar |