| 100% | TRUEGRIT | 8 | 1969 Western that won 44-Across an Oscar: 2 wds. |
| 56% | LESMISERABLES | 13 | 2012 film that won Anne Hathaway an Oscar: 2 wds. |
| 48% | CASSIDYANDTHE | 13 | "Butch ___ Sundance Kid," 1969 Western film based on the outlaws Robert LeRoy Parker and Harry Longabaugh that won four Oscars: 3 wds. |
| 47% | HOLIDAYINN | 10 | 1942 film that won a Best Original Song Oscar for 34-Across: 2 wds. |
| 47% | TRAININGDAY | 11 | 2001 thriller directed by Antoine Fuqua that won an Oscar for Best Actor (2 wds.) |
| 46% | GOSFORDPARK | 11 | 2001 drama directed by Robert Altman that won an Oscar for Best Original Screenplay (2 wds.) |
| 46% | LALA | 4 | "___ Land," 2016 film that won Emma Stone an Oscar for Best Actress: 2 wds. |
| 43% | LONESOMEDOVE | 12 | Western novel that won the 1986 Pulitzer Prize: 2 wds. |
| 43% | THEFATHER | 9 | 2020 Anthony Hopkins movie that won two Oscars, including Best Actor: 2 wds. |
| 43% | LETITGO | 7 | "Frozen" song that won an Oscar for Best Original Song in 2014 (3 wds.) |
| 42% | WHITECHRISTMAS | 14 | Irivng Berlin song sung by 53-Across in 16-Across that won an Oscar for Best Original Song (2 wds.) |
| 42% | SHOTA | 5 | "He ___ portrait that won him an award.": 2 wds. |
| 42% | LALA | 4 | "___ Land" (2016 film that won six Oscars): 2 wds. |
| 42% | JULIEANDREWS | 12 | Actress who won an Oscar for playing the title role in 39-Across: 2 wds. |
| 42% | WESTSIDESTORY | 13 | 1961 movie musical about rival street gangs that won an Oscar for Best Picture: 3 wds. |
| 42% | CITYOFSTARS | 11 | "La La Land" song that won an Oscar for Best Original Song in 2017 (3 wds.) |
| 42% | ROSAMUNDPIKE | 12 | "Saltburn" actress who was nominated for an Oscar for her role in 44-Across (2 wds.) |
| 41% | GOINGMYWAY | 10 | 1944 movie musical about a young parish priest that won an Oscar for Best Picture: 3 wds. |
| 41% | MYFAIRLADY | 10 | 1964 movie musical about a Cockney flower girl that won an Oscar for Best Picture: 3 wds. |
| 41% | FINDINGNEMO | 11 | 2003 Pixar film about a lost fish that won the Oscar for Best Animated Feature: 2 wds. |
| 41% | FIGHTFORYOU | 11 | "Judas and the Black Messiah" song that won an Oscar for Best Original Song in 2021 (3 wds.) |
| 40% | RAINMAN | 7 | 1988 film that won Dustin Hoffman his second Oscar: 2 wds. |
| 40% | BLACKSWAN | 9 | Film for which Natalie Portman won an Oscar: 2 wds. |
| 40% | INABETTERWORLD | 14 | 2010 Danish thriller set in Denmark and Sudan that won an Oscar for Best Foreign Language Film (4 wds.) |
| 40% | WHATWASI | 8 | With 48-Across, Billie Eilish hit from "Barbie" that won an Oscar for Best Original Song: 3 wds. |
| 40% | SCHINDLERSLIST | 14 | 1993 historical drama about the Holocaust that won both the Best Picture Oscar and the Best Film BAFTA: 2 wds. |
| 40% | PANSLABYRINTH | 13 | 2006 fantasy from Spain and Mexico that won Oscars for Best Cinematography, Best Art Direction, and Best Makeup: 2 wds. |
| 39% | JOANCRAWFORD | 12 | Actress who won an Oscar for 1945's "Mildred Pierce": 2 wds. |
| 39% | THEGREATEST | 11 | With 42-Across, 1952 circus film that won the Best Picture Oscar: 2 wds. |
| 39% | JULIANNEMOORE | 13 | Redheaded actress who won an Oscar for "Still Alice": 2 wds. |