| 100% | ROBINWILLIAMS | 13 | "Good Will Hunting" Oscar winner who plays the title nanny in "Mrs. Doubtfire" (2 wds.) |
| 74% | ROBINWILLIAMS | 13 | "Good Will Hunting" actor who played the nanny Mrs. Doubtfire in the 1993 film: 2 wds. |
| 69% | EMMATHOMPSON | 12 | "Howards End" Oscar winner who plays the title nanny in the "Nanny McPhee" films (2 wds.) |
| 65% | ROBINWILLIAMS | 13 | "Good Will Hunting" actor who played Daniel Hillard and the title housekeeper in "Mrs. Doubtfire" (2 wds.) |
| 58% | SAMROCKWELL | 11 | "Three Billboards Outside Ebbing, Missouri" Oscar winner who played the title choreographer in 45-Across: 2 wds. |
| 54% | JULIEANDREWS | 12 | Actress who won an Oscar for playing the title nanny in "Mary Poppins" (2 wds.) |
| 53% | TILDASWINTON | 12 | "Michael Clayton" Best Supporting Actress Oscar winner who plays The Ancient One in Marvel's "Doctor Strange" (2 wds.) |
| 53% | ROBINWILLIAMS | 13 | "Good Will Hunting" actor who played Theodore Roosevelt in 2006's "Night at the Museum": 2 wds. |
| 53% | MATTDAMON | 9 | "Good Will Hunting" star who played fallen angel Loki in the 1999 film "Dogma": 2 wds. |
| 52% | ERNESTBORGNINE | 14 | "Marty" Oscar winner who played the detective Mike Rogo in "The Poseidon Adventure" (2 wds.) |
| 51% | MICHAELDOUGLAS | 14 | "Wall Street" Best Actor Oscar winner who plays Hank Pym in the Marvel Cinematic Universe (2 wds.) |
| 51% | JAMESCAGNEY | 11 | "Yankee Doodle Dandy" Oscar winner who played Bottom in the 1935 film version of "A Midsummer Night's Dream": 2 wds. |
| 50% | TIMOTHYHUTTON | 13 | "Ordinary People" Oscar winner who plays the father of 50-Across in a 2020 biopic (2 wds.) |
| 50% | CHARLIZETHERON | 14 | "Monster" Oscar winner who was Harvard's Hasty Pudding Woman of the Year in 2008: 2 wds. |
| 50% | RAMIMALEK | 9 | "Bohemian Rhapsody" Oscar winner who was in the James Bond movie "No Time to Die": 2 wds. |
| 50% | CHRISTIANBALE | 13 | "The Fighter" Oscar winner who played Demetrius in the 1999 film version of "A Midsummer Night's Dream": 2 wds. |
| 50% | HELENMIRREN | 11 | "The Queen" Oscar winner who played Hermia in the 1968 film version of "A Midsummer Night's Dream": 2 wds. |
| 50% | RENEEZELLWEGER | 14 | "Cold Mountain" Oscar winner who was Harvard's Hasty Pudding Woman of the Year in 2009: 2 wds. |
| 50% | ROBINWILLIAMS | 13 | "Good Will Hunting" actor who plays President Dwight D. Eisenhower in the 2013 film "The Butler" (2 wds.) |
| 49% | OCTAVIASPENCER | 14 | "The Help" Oscar winner who was Harvard's Hasty Pudding Woman of the Year in 2017: 2 wds. |
| 49% | AMYPOEHLER | 10 | Actress who played the role of Leslie Knope in "Parks and Recreation", a role she is best-known for: 2 wds. |
| 49% | FORESTWHITAKER | 14 | "The Last King of Scotland" Best Actor Oscar winner who plays Zuri in the MCU (2 wds.) |
| 49% | SIDNEYPOITIER | 13 | "Lilies of the Field" Oscar winner who played Donald Crease in "Sneakers": 2 wds. |
| 48% | ROBINWILLIAMS | 13 | "Good Will Hunting" actor who played Armand Goldman in "The Birdcage" (2 wds.) |
| 48% | MARLONBRANDO | 12 | "On the Waterfront" Oscar winner who won (and declined) a Best Actor Oscar for playing Vito Corleone in 47-Across (2 wds.) |
| 48% | JACKPALANCE | 11 | "City Slickers" Oscar winner who plays twin brothers Curly and Duke Washburn in the "City Slickers" films (2 wds.) |
| 48% | ROBINWILLIAMS | 13 | Actor who played Daniel Hillard, and the title character, in the 1993 film "Mrs. Doubtfire": 2 wds. |
| 48% | JULIEANDREWS | 12 | Actress who won an Oscar for playing the title role in 39-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.) |
| 47% | ALLISONJANNEY | 13 | "I, Tonya" Oscar winner who plays Colonel Howell in "The Creator" (2 wds.) |