| 100% | SIDNEYPOITIER | 13 | "Lilies of the Field" Oscar winner who played Donald Crease in "Sneakers": 2 wds. |
| 61% | CHRISTIANBALE | 13 | "The Fighter" Oscar winner who played Demetrius in the 1999 film version of "A Midsummer Night's Dream": 2 wds. |
| 61% | HELENMIRREN | 11 | "The Queen" Oscar winner who played Hermia in the 1968 film version of "A Midsummer Night's Dream": 2 wds. |
| 60% | JAMESCAGNEY | 11 | "Yankee Doodle Dandy" Oscar winner who played Bottom in the 1935 film version of "A Midsummer Night's Dream": 2 wds. |
| 59% | SIDNEYPOITIER | 13 | 1964 Best Actor Oscar winner for playing Homer Smith in "Lilies of the Field": 2 wds. |
| 58% | TIMOTHYHUTTON | 13 | "Ordinary People" Oscar winner who plays the father of 50-Across in a 2020 biopic (2 wds.) |
| 55% | SAMROCKWELL | 11 | "Three Billboards Outside Ebbing, Missouri" Oscar winner who played the title choreographer in 45-Across: 2 wds. |
| 53% | OCTAVIASPENCER | 14 | "The Help" Oscar winner who was Harvard's Hasty Pudding Woman of the Year in 2017: 2 wds. |
| 53% | CHARLIZETHERON | 14 | "Monster" Oscar winner who was Harvard's Hasty Pudding Woman of the Year in 2008: 2 wds. |
| 53% | RENEEZELLWEGER | 14 | "Cold Mountain" Oscar winner who was Harvard's Hasty Pudding Woman of the Year in 2009: 2 wds. |
| 52% | ERNESTBORGNINE | 14 | "Marty" Oscar winner who played the detective Mike Rogo in "The Poseidon Adventure" (2 wds.) |
| 52% | ROBINWILLIAMS | 13 | "Good Will Hunting" Oscar winner who plays the title nanny in "Mrs. Doubtfire" (2 wds.) |
| 52% | NICOLASCAGE | 11 | Oscar winner who stars in the 1998 film "City of Angels" (2 wds.) |
| 52% | EMMATHOMPSON | 12 | "Howards End" Oscar winner who plays the title nanny in the "Nanny McPhee" films (2 wds.) |
| 51% | NICOLASCAGE | 11 | "Leaving Las Vegas" Oscar winner who plays twin brothers Charlie and Donald Kaufman in "Adaptation" (2 wds.) |
| 51% | FORESTWHITAKER | 14 | "The Last King of Scotland" Best Actor Oscar winner who plays Zuri in the MCU (2 wds.) |
| 51% | JACKPALANCE | 11 | "City Slickers" Oscar winner who plays twin brothers Curly and Duke Washburn in the "City Slickers" films (2 wds.) |
| 51% | TILDASWINTON | 12 | "Michael Clayton" Best Supporting Actress Oscar winner who plays The Ancient One in Marvel's "Doctor Strange" (2 wds.) |
| 49% | DIANNEWIEST | 11 | "Bullets Over Broadway" Oscar winner who plays the mother on 29-/32-Across: 2 wds. |
| 48% | GENEHACKMAN | 11 | "The French Connection" and "Unforgiven" Oscar winner who played the minister Frank Scott in "The Poseidon Adventure" (2 wds.) |
| 48% | MARLONBRANDO | 12 | Two-time Oscar winner who portrayed the rogue colonel in 31-Across: 2 wds |
| 48% | ROBERTREDFORD | 13 | "The Sting" Oscar nominee who played Martin Bishop in the 1992 heist movie "Sneakers": 2 wds. |
| 47% | EMMATHOMPSON | 12 | "Howard's End" Oscar winner who was appointed a Dame Commander of the Order of the British Empire (DBE) in 2018 (2 wds.) |
| 47% | ANTHONYHOPKINS | 14 | "The Silence of the Lambs" and "The Father" Best Actor Oscar winner who plays Odin in the MCU (2 wds.) |
| 47% | ADRIENBRODY | 11 | "The Pianist" Oscar winner who plays a Hollywood film director working in a London theater in 31-Across (2 wds.) |
| 47% | CHRISTIANBALE | 13 | "The Fighter" Oscar winner who plays (spoiler alert!) twin brothers Alfred Borden and Bernard Fallon in "The Prestige" (2 wds.) |
| 47% | EMMATHOMPSON | 12 | Oscar-winning actress who plays P.L. Travers, author of the novel "Mary Poppins," in 32-Across: 2 wds. |
| 47% | JAMIEFOXX | 9 | Oscar winner who plays jazz pianist Joe Gardner in 1-Across (2 wds.) |
| 47% | MICHAELDOUGLAS | 14 | "Wall Street" Best Actor Oscar winner who plays Hank Pym in the Marvel Cinematic Universe (2 wds.) |
| 47% | MERYLSTREEP | 11 | "The Iron Lady" Oscar winner who plays Aunt March in 36-Across (2 wds.) |