| 100% | MARLONBRANDO | 12 | 1972 Best Actor Oscar winner who played 21-Across: 2 wds. |
| 64% | FORESTWHITAKER | 14 | "The Last King of Scotland" Best Actor Oscar winner who plays Zuri in the MCU (2 wds.) |
| 64% | MICHAELDOUGLAS | 14 | "Wall Street" Best Actor Oscar winner who plays Hank Pym in the Marvel Cinematic Universe (2 wds.) |
| 63% | ANTHONYHOPKINS | 14 | "The Silence of the Lambs" and "The Father" Best Actor Oscar winner who plays Odin in the MCU (2 wds.) |
| 60% | MARLONBRANDO | 12 | "On the Waterfront" Oscar winner who won (and declined) a Best Actor Oscar for playing Vito Corleone in 47-Across (2 wds.) |
| 59% | MAHERSHALAALI | 13 | Two-time Best Supporting Actor Oscar winner who plays Wayne Hayes in season 3 of 43-Across (2 wds.) |
| 56% | REXHARRISON | 11 | 1965 Best Actor Oscar winner for playing Henry Higgins in "My Fair Lady": 2 wds. |
| 56% | SIDNEYPOITIER | 13 | 1964 Best Actor Oscar winner for playing Homer Smith in "Lilies of the Field": 2 wds. |
| 56% | GREGORYPECK | 11 | 1963 Best Actor Oscar winner for playing Atticus Finch in "To Kill a Mockingbird": 2 wds. |
| 56% | JAMIEFOXX | 9 | "Ray" Best Actor Oscar winner who turns 50 on December 13, 2017 (2 wds.) |
| 55% | HILARYSWANK | 11 | Two-time Best Actress Oscar winner who plays Bridget in 46-Across (2 wds.) |
| 54% | 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. |
| 53% | DIANNEWIEST | 11 | "Bullets Over Broadway" Oscar winner who plays the mother on 29-/32-Across: 2 wds. |
| 53% | JODIEFOSTER | 11 | Two-time Best Actress Oscar winner who plays Liz Danvers in season 4 of 43-Across (2 wds.) |
| 52% | SAMROCKWELL | 11 | "Three Billboards Outside Ebbing, Missouri" Oscar winner who played the title choreographer in 45-Across: 2 wds. |
| 51% | DANIELKALUUYA | 13 | "Get Out" Best Actor Oscar nominee who plays Jatemme Manning in "Widows" (2 wds.) |
| 51% | JAMIEFOXX | 9 | Oscar winner who plays jazz pianist Joe Gardner in 1-Across (2 wds.) |
| 50% | BENKINGSLEY | 11 | Winner of a Best Actor Oscar for playing Gandhi, the title role of 1982's Best Picture: 2 wds. |
| 50% | MICHAELSHANNON | 14 | Two-time Best Supporting Actor Oscar nominee who plays Nicky in 46-Across (2 wds.) |
| 50% | BRENDANFRASER | 13 | 2023 Best Actor Oscar winner for his role in "The Whale": 2 wds. |
| 50% | ANTHONYHOPKINS | 14 | Best Actor Oscar winner for both "The Silence of the Lambs" and "The Father": 2 wds. |
| 50% | LIAMNEESON | 10 | "Schindler's List" Best Actor Oscar nominee who plays Harry Rawlins in "Widows" (2 wds.) |
| 50% | SIDNEYPOITIER | 13 | "Lilies of the Field" Oscar winner who played Donald Crease in "Sneakers": 2 wds. |
| 50% | CHARLTONHESTON | 14 | Winner of a Best Actor Oscar for playing Judah Ben-Hur, the title role of 1959's Best Picture: 2 wds. |
| 50% | MERYLSTREEP | 11 | "The Iron Lady" Oscar winner who plays Aunt March in 36-Across (2 wds.) |
| 49% | DANIELDAYLEWIS | 14 | Best Actor Oscar winner for "My Left Foot," "There Will Be Blood," and "Lincoln": 2 wds., hyph. |
| 49% | SEANPENN | 8 | Best Actor Oscar winner for "Milk" and "Mystic River" (2 wds.) |
| 49% | JULIANNEMOORE | 13 | "Still Alice" Oscar winner who plays 50-Across in a 2020 biopic (2 wds.) |
| 48% | TIMOTHYHUTTON | 13 | "Ordinary People" Oscar winner who plays the father of 50-Across in a 2020 biopic (2 wds.) |
| 48% | DUSTINHOFFMAN | 13 | Best Actor Oscar nominee for playing Benjamin Braddock in 28-Across (2 wds.) |