| 100% | NOMADLAND | 9 | 50-Across film that won Academy Awards in 2021 for Best Picture, Best Actress, and Best Director |
| 55% | WINGS | 5 | 1927 film starring Clara Bow that won the first Academy Award for Best Picture in 1929 |
| 52% | LIST | 4 | "Schindler's ___," historical drama film that won an Academy Award for Best Picture in the '90s |
| 51% | LAMBS | 5 | "The Silence of the ___," psychological horror film that won an Academy Award for Best Picture in the '90s |
| 49% | PARASITE | 8 | Film that won four Academy Awards in 2020, including Best Picture |
| 47% | HEAT | 4 | "In the ___ of the Night," 1967 film starring Sidney Poitier that won the Academy Award for Best Picture |
| 47% | HER | 3 | One-named singer who won the Academy Award for Best Original Song in 2021 for "Fight for You" from the film "Judas and the Black Messiah" |
| 47% | CAVALCADE | 9 | 1933 drama film that won Oscars for Best Picture, and Best Director for Frank Lloyd |
| 47% | LADYBIRD | 8 | 2017 coming-of-age film that received nominations for Best Picture, Best Director and Best Actress |
| 46% | PARASITE | 8 | Film that won four Academy Awards in 2020, including Best Picture (the first foreign-language film to do so) |
| 45% | COWBOY | 6 | "Midnight ___," 1969 film starring Dustin Hoffman that won the Academy Award for Best Picture |
| 45% | APARTMENT | 9 | "The ___," 1960 film starring Jack Lemmon that won the Academy Award for Best Picture |
| 45% | ABEAUTIFULMIND | 14 | 2001 biopic directed by Ron Howard that won Oscars for Best Picture, Best Director, Best Supporting Actress, and Best Adapted Screenplay (3 wds.) |
| 45% | TOM | 3 | "___ Jones," 1963 British film starring Albert Finney that won the Academy Award for Best Picture |
| 45% | ARABIA | 6 | "Lawrence of ___," 1962 British film starring Alec Guinness that won the Academy Award for Best Picture |
| 45% | STING | 5 | "The ___," heist film starring Paul Newman which won the Academy Award for Best Picture in 1974 |
| 45% | GODFATHER | 9 | "The ___," crime film starring Marlon Brando which won the Academy Award for Best Picture in 1973 |
| 44% | GLADIATOR | 9 | Russell Crowe film that won Best Picture at the 73rd Academy Awards and was the second-highest grossing film of 2000 |
| 44% | EEAAO | 5 | A24 film that won Best Picture in 2023, for short |
| 44% | ROCKY | 5 | American sports drama film starring Sylvester Stallone which won the Academy Award for Best Picture in 1977 |
| 44% | CHLOEZHAO | 9 | 16-Across director who won an Academy Award for Best Director in 2021, becoming the first non-white woman to win a directing Oscar (2 wds.) |
| 44% | SEASONS | 7 | "A Man for All ___," 1966 British film starring Paul Scofield that won the Academy Award for Best Picture |
| 44% | FRANK | 5 | ___ Borzage, film director who won the first Academy Award for the best director for "7th Heaven" in 1929 |
| 43% | FLEW | 4 | "One ___ Over the Cuckoo's Nest," 1975 film produced by Michael Douglas that won the Academy Award for Best Picture |
| 43% | HUNTER | 6 | "The Deer ___," epic war drama film starring Robert De Niro which won the Academy Award for Best Picture in 1979 |
| 43% | JULIEANDREWS | 12 | Performer who won an Academy Award for Best Actress for playing the title character in her film debut, "Mary Poppins" (2 wds.) |
| 42% | SHIRLEYBOOTH | 12 | Performer who won an Academy Award for Best Actress for playing Lola Delaney in her film debut, "Come Back, Little Sheba" (2 wds.) |
| 42% | BELONG | 6 | "Up Where We ___," song from the movie "An Officer and a Gentleman" that won the Academy Award for Best Original Song in 1982 |
| 42% | BOYSDONTCRY | 11 | 1999 film for which 46-Across won an Academy Award for Best Actress (3 wds.) |
| 42% | MARLEEMATLIN | 12 | Performer who won an Academy Award for Best Actress for playing Sarah Norman in her film debut, "Children of a Lesser God" (2 wds.) |