| 100% | USUALSUSPECTS | 13 | 1995 crime film for which Kevin Spacey won an Oscar, with "The": 2 wds. |
| 58% | BLINDSIDE | 9 | With "The," 2009 film for which 34-Across won an Oscar: 2 wds. |
| 57% | MIRACLEWORKER | 13 | With "The," 1962 film for which 15-Across won an Oscar for portraying Helen Keller: 2 wds. |
| 54% | BLACKSWAN | 9 | Film for which Natalie Portman won an Oscar: 2 wds. |
| 52% | NORMARAE | 8 | 1979 film for which Sally Field won an Oscar: 2 wds. |
| 52% | LILIESOF | 8 | With 44-Across, film for which 30-Across won the Oscar for Best Actor: 2 wds. |
| 52% | TRAININGDAY | 11 | 2001 Ethan Hawke starrer crime thriller film for which Denzel Washington won an Oscar award for Best Actor: 2 wds. |
| 50% | GREENBOOK | 9 | Film for which 32-Across won the Best Supporting Actor Oscar in 2019: 2 wds. |
| 48% | THEHELP | 7 | 2011 film for which Octavia Spencer won the Oscar for Best Supporting Actress: 2 wds. |
| 46% | SCHINDLERSLIST | 14 | 1993 film for which 46-Across won a Grammy Award and an Oscar (2 wds.) |
| 44% | NORMARAE | 8 | 1979 movie for which Sally Field won an Oscar: 2 wds. |
| 43% | JENNIFERHUDSON | 14 | Actress who won an Oscar for her first feature film role, in "Dreamgirls": 2 wds. |
| 43% | JULIEANDREWS | 12 | Actress who won an Oscar for playing the title role in 39-Across: 2 wds. |
| 43% | THEGRADUATE | 11 | 1967 film for which 18-Across won his Best Director Oscar: 2 wds. |
| 43% | STILLALICE | 10 | 2014 film for which 30-Across recently won an Academy Award for Best Actress: 2 wds. |
| 43% | JULIEANDREWS | 12 | Actress who won an Oscar for her first feature film role, in "Mary Poppins": 2 wds. |
| 43% | NICOLEKIDMAN | 12 | Actress who won an Oscar for Best Actress for "The Hours" and a Worst Screen Couple Razzie Award with Will Ferrell for "Bewitched": 2 wds. |
| 43% | LALA | 4 | "___ Land" (movie for which Emma Stone won an Oscar): 2 wds. |
| 43% | THEPIANO | 8 | Film for which Holly Hunter won an Oscar |
| 43% | SAMSMITH | 8 | Nonbinary singer who won an Oscar for the Bond theme "Writing's on the Wall": 2 wds. |
| 43% | SIDNEYPOITIER | 13 | Star of 15- and 34-Across who won an Oscar for "Lilies of the Field": 2 wds. |
| 42% | LUPITANYONGO | 12 | Actress who won an Oscar for her first feature film role, in "12 Years a Slave": 2 wds. |
| 42% | LILIESOF | 8 | With 64-Across, film for which 47-Across won an Oscar for Best Actor |
| 41% | DARKESTHOUR | 11 | A 2017 war drama film for which actor Gary Oldman (birthday today) won the Academy Award for Best Actor: 2 wds. |
| 41% | KEVINCOSTNER | 12 | Actor who plays Frank Farmer in 18a and has also won an Oscar for Best Director for "Dances with Wolves": 2 wds. |
| 41% | MICHAEL | 7 | With 32-Across, 2007 film for which Tilda Swinton won an Oscar for her portrayal of lawyer Karen Crowder |
| 41% | ROOM | 4 | 2015 film for which Brie Larson won an Oscar |
| 41% | TOOTSIE | 7 | 1982 film for which Jessica Lange won an Oscar |
| 40% | GREENBOOK | 9 | 2018 film for which 47-Across won a Best Supporting Actor Oscar (2 wds.) |
| 40% | MARTINSCORSESE | 14 | New Hollywood director who won an Oscar for "The Departed," and is the most-nominated director alive in terms of Oscars: 2 wds. |