| 100% | ROBERTREDFORD | 13 | He won the Best Director Oscar for the first film he directed, 1980's "Ordinary People": 2 wds. |
| 81% | KEVINCOSTNER | 12 | He won the Best Director Oscar for the first film he directed, 1990's "Dances With Wolves": 2 wds. |
| 76% | JAMESLBROOKS | 12 | He won the Best Director Oscar for the first film he directed, 1983's "Terms of Endearment": 3 wds. |
| 55% | 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. |
| 53% | TIMOTHYHUTTON | 13 | Actor who won a Best Supporting Actor Oscar for his first role in a feature film (Conrad Jarrett in 1980's "Ordinary People") (2 wds.) |
| 52% | ALFONSOCUARON | 13 | First Mexican to win the Best Director Oscar (for "Gravity"): 2 wds. |
| 51% | KATHRYNBIGELOW | 14 | Woman who won the Best Director Oscar for 2009's "The Hurt Locker": 2 wds. |
| 50% | CLINTEASTWOOD | 13 | Oldest person to win the Best Director Oscar, at 74 (for "Million Dollar Baby"): 2 wds. |
| 48% | BOBFOSSE | 8 | "All That Jazz" filmmaker who won the Best Director Oscar for "Cabaret": 2 wds. |
| 47% | 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.) |
| 47% | JASONROBARDS | 12 | He won two Best Supporting Actor Oscars, for "All the President's Men" and "Julia": 2 wds. |
| 46% | THEGRADUATE | 11 | 1967 film for which 18-Across won his Best Director Oscar: 2 wds. |
| 46% | ALFONSOCUARON | 13 | Best Director Oscar winner for the 2018 film "Roma": 2 wds. |
| 45% | DALLASBUYERS | 12 | "___ Club," 2013 biography-drama starring Matthew McConaughey (birthday today), for which he won the Best Actor Oscar: 2 wds. |
| 45% | GREENBOOK | 9 | Film for which 32-Across won the Best Supporting Actor Oscar in 2019: 2 wds. |
| 44% | CHRISTIANBALE | 13 | He won the Oscar and Golden Globe for Best Supporting Actor for 18-Across: 2 wds. |
| 44% | GEOFFREYRUSH | 12 | Australian actor who won the Best Actor Oscar for 1996's "Shine": 2 wds. |
| 44% | HALLEBERRY | 10 | First Black woman to win the Oscar for Best Actress: 2 wds. |
| 44% | NICOLEKIDMAN | 12 | Australian actress who won the Best Actress Oscar for 2002's "The Hours": 2 wds. |
| 44% | CATEBLANCHETT | 13 | Australian actress who won the Best Actress Oscar for 2013's "Blue Jasmine": 2 wds. |
| 44% | 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.) |
| 44% | SIDNEYPOITIER | 13 | First black person to win the Academy Award for Best Actor: 2 wds. |
| 44% | ASEPARATION | 11 | 2011 family drama that was the first Iranian film to win an Oscar for Best Foreign Language Film (2 wds.) |
| 43% | SIDNEY | 6 | Actor and director Poitier, the first black person to win an Oscar for best actor |
| 43% | THEHELP | 7 | 2011 film for which Octavia Spencer won the Oscar for Best Supporting Actress: 2 wds. |
| 42% | 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.) |
| 42% | LILIESOF | 8 | With 44-Across, film for which 30-Across won the Oscar for Best Actor: 2 wds. |
| 42% | LIZAMINNELLI | 12 | "Arthur" actress who won the Best Actress Oscar for "Cabaret": 2 wds. |
| 42% | JAMESCAMERON | 12 | Filmmaker who won three Oscars (Best Picture, Director, and Film Editing) for 1997's "Titanic": 2 wds. |
| 42% | FINDINGNEMO | 11 | 2003 Pixar film about a lost fish that won the Oscar for Best Animated Feature: 2 wds. |