| 100% | KEVINCOSTNER | 12 | He won the Best Director Oscar for the first film he directed, 1990's "Dances With Wolves": 2 wds. |
| 77% | ROBERTREDFORD | 13 | He won the Best Director Oscar for the first film he directed, 1980's "Ordinary People": 2 wds. |
| 72% | JAMESLBROOKS | 12 | He won the Best Director Oscar for the first film he directed, 1983's "Terms of Endearment": 3 wds. |
| 52% | MIKENICHOLS | 11 | New Hollywood director of "Who's Afraid of Virginia Woolf?" who won the Best Director Oscar for his second film, "The Graduate": 2 wds. |
| 49% | ALFONSOCUARON | 13 | First Mexican to win the Best Director Oscar (for "Gravity"): 2 wds. |
| 48% | KATHRYNBIGELOW | 14 | Woman who won the Best Director Oscar for 2009's "The Hurt Locker": 2 wds. |
| 46% | KEVINCOSTNER | 12 | Actor who plays Frank Farmer in 18a and has also won an Oscar for Best Director for "Dances with Wolves": 2 wds. |
| 46% | KEVINCOSTNER | 12 | Best Director Oscar winner for "Dances With Wolves" who was a Worst Director Razzie winner for "The Postman": 2 wds. |
| 46% | LILIESOF | 8 | With 44-Across, film for which 30-Across won the Oscar for Best Actor: 2 wds. |
| 46% | BOBFOSSE | 8 | "All That Jazz" filmmaker who won the Best Director Oscar for "Cabaret": 2 wds. |
| 45% | 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% | JASONROBARDS | 12 | He won two Best Supporting Actor Oscars, for "All the President's Men" and "Julia": 2 wds. |
| 44% | THEGREATEST | 11 | With 42-Across, 1952 circus film that won the Best Picture Oscar: 2 wds. |
| 44% | DALLASBUYERS | 12 | "___ Club," 2013 biography-drama starring Matthew McConaughey (birthday today), for which he won the Best Actor Oscar: 2 wds. |
| 43% | THEGRADUATE | 11 | 1967 film for which 18-Across won his Best Director Oscar: 2 wds. |
| 43% | ALFONSOCUARON | 13 | Best Director Oscar winner for the 2018 film "Roma": 2 wds. |
| 43% | CHRISTIANBALE | 13 | He won the Oscar and Golden Globe for Best Supporting Actor for 18-Across: 2 wds. |
| 42% | GREENBOOK | 9 | Film for which 32-Across won the Best Supporting Actor Oscar in 2019: 2 wds. |
| 42% | GEOFFREYRUSH | 12 | Australian actor who won the Best Actor Oscar for 1996's "Shine": 2 wds. |
| 42% | HALLEBERRY | 10 | First Black woman to win the Oscar for Best Actress: 2 wds. |
| 41% | NICOLEKIDMAN | 12 | Australian actress who won the Best Actress Oscar for 2002's "The Hours": 2 wds. |
| 41% | CATEBLANCHETT | 13 | Australian actress who won the Best Actress Oscar for 2013's "Blue Jasmine": 2 wds. |
| 41% | JULIEANDREWS | 12 | Actress who won a Best Actress Oscar for her first role in a feature film (Mary Poppins in 1964's "Mary Poppins") (2 wds.) |
| 41% | ASEPARATION | 11 | 2011 family drama that was the first Iranian film to win an Oscar for Best Foreign Language Film (2 wds.) |
| 41% | CLINTEASTWOOD | 13 | Oldest person to win the Best Director Oscar, at 74 (for "Million Dollar Baby"): 2 wds. |
| 41% | JUSTINHURWITZ | 13 | American composer who won the 2017 Oscar for Best Original Score for the film "La La Land": 2 wds. |
| 41% | KEVINCOSTNER | 12 | Director and star of 1990's "Dances With Wolves": 2 wds. |
| 40% | THEHELP | 7 | 2011 film for which Octavia Spencer won the Oscar for Best Supporting Actress: 2 wds. |
| 40% | LOUISEFLETCHER | 14 | Actress who won a Best Actress Oscar for playing 46-Across in the 1975 film "One Flew Over the Cuckoo's Nest" (2 wds.) |
| 40% | BLINDSIDE | 9 | With "The," 2009 film for which 34-Across won an Oscar: 2 wds. |