| 100% | SEANPENN | 8 | Best Actor Oscar winner for "Milk" and "Mystic River" (2 wds.) |
| 81% | SEAN | 4 | With 57-Across, Best Actor Oscar winner for "Milk" and "Mystic River" |
| 79% | PENN | 4 | Best Actor Oscar winner for "Mystic River" and "Milk" |
| 78% | PENN | 4 | Sean —, Best Actor in a Leading Role Oscar winner for Milk and Mystic River |
| 76% | SEAN | 4 | With 38-Across, Best Actor Oscar winner for both "Mystic River" and "Milk" |
| 76% | ANTHONYHOPKINS | 14 | Best Actor Oscar winner for both "The Silence of the Lambs" and "The Father": 2 wds. |
| 75% | DANIELDAYLEWIS | 14 | Best Actor Oscar winner for "My Left Foot," "There Will Be Blood," and "Lincoln": 2 wds., hyph. |
| 67% | BRENDANFRASER | 13 | 2023 Best Actor Oscar winner for his role in "The Whale": 2 wds. |
| 66% | REXHARRISON | 11 | 1965 Best Actor Oscar winner for playing Henry Higgins in "My Fair Lady": 2 wds. |
| 66% | SIDNEYPOITIER | 13 | 1964 Best Actor Oscar winner for playing Homer Smith in "Lilies of the Field": 2 wds. |
| 66% | GREGORYPECK | 11 | 1963 Best Actor Oscar winner for playing Atticus Finch in "To Kill a Mockingbird": 2 wds. |
| 65% | GENEHACKMAN | 11 | Winner of a Best Actor Oscar for "The French Connection" and a Best Supporting Actor Oscar for "Unforgiven": 2 wds. |
| 65% | BENKINGSLEY | 11 | 1982 Best Actor Oscar winner for "Gandhi" (2 wds.) |
| 63% | MARLONBRANDO | 12 | Best Actor Oscar winner for "On the Waterfront" who was a Worst Supporting Actor Razzie winner for "The Island of Dr. Moreau": 2 wds. |
| 63% | MAHERSHALAALI | 13 | Best Supporting Actor Oscar winner for the 2018 film "Green Book": 2 wds. |
| 61% | ARTCARNEY | 9 | Best Actor Oscar winner for 1974's "Harry and Tonto" |
| 61% | BRADPITT | 8 | Best Supporting Actor Oscar winner for the 2019 film "Once Upon a Time in Hollywood": 2 wds. |
| 61% | CILLIANMURPHY | 13 | 2024 Best Actor Oscar winner for portraying Manhattan Project physicist J. Robert Oppenheimer in "Oppenheimer" (2 wds.) |
| 60% | HENRYFONDA | 10 | 1981 Oscar winner for "On Golden Pond" (Best Actor): 2 wds. |
| 60% | LOUGOSSETTJR | 12 | 1982 Best Supporting Actor Oscar winner for "An Officer and a Gentleman" (3 wds.) |
| 58% | MARLONBRANDO | 12 | 1972 Best Actor Oscar winner who played 21-Across: 2 wds. |
| 58% | SEANPENN | 8 | Oscar winner for "Mystic River" and "Milk" |
| 57% | SEANPENN | 8 | Oscar winner for playing Harvey Milk: 2 wds. |
| 57% | SEANPENN | 8 | Actor famous for "Milk" and "Mystic River" who appeared as a guest star on "Friends": 2 wds. |
| 57% | BRENDANFRASER | 13 | Best Actor Oscar winner for his portrayal of a reclusive English teacher trying to reconnect with his daughter in the 2022 film "The Whale" (2 wds.) |
| 57% | ALFONSOCUARON | 13 | Best Director Oscar winner for the 2018 film "Roma": 2 wds. |
| 57% | RENEEZELLWEGER | 14 | Best Actress Oscar winner for the 2019 film "Judy": 2 wds. |
| 57% | BENKINGSLEY | 11 | Winner of a Best Actor Oscar for playing Gandhi, the title role of 1982's Best Picture: 2 wds. |
| 56% | CHARLTONHESTON | 14 | Winner of a Best Actor Oscar for playing Judah Ben-Hur, the title role of 1959's Best Picture: 2 wds. |
| 55% | AUSTINBUTLER | 12 | Best Actor Oscar nominee for his portrayal of the "King of Rock and Roll" in the 2022 film "Elvis" (2 wds.) |