| 100% | HILARYSWANK | 11 | Two-time Best Actress Oscar winner who plays Bridget in 46-Across (2 wds.) |
| 76% | JODIEFOSTER | 11 | Two-time Best Actress Oscar winner who plays Liz Danvers in season 4 of 43-Across (2 wds.) |
| 64% | MICHAELSHANNON | 14 | Two-time Best Supporting Actor Oscar nominee who plays Nicky in 46-Across (2 wds.) |
| 60% | MAHERSHALAALI | 13 | Two-time Best Supporting Actor Oscar winner who plays Wayne Hayes in season 3 of 43-Across (2 wds.) |
| 57% | ANGELINAJOLIE | 13 | "Girl, Interrupted" Best Supporting Actress Oscar winner who plays Thena in Marvel's "Eternals" (2 wds.) |
| 55% | SANDRABULLOCK | 13 | "The Blind Side" Best Actress Oscar winner who starred in 15-Across, 24-Across, 31-Across, and 40-Across (2 wds.) |
| 55% | TILDASWINTON | 12 | "Michael Clayton" Best Supporting Actress Oscar winner who plays The Ancient One in Marvel's "Doctor Strange" (2 wds.) |
| 54% | 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.) |
| 54% | LUPITANYONGO | 12 | "12 Years a Slave" Best Supporting Actress Oscar winner who plays Nakia in Marvel's "Black Panther" (2 wds.) |
| 53% | MARLONBRANDO | 12 | 1972 Best Actor Oscar winner who played 21-Across: 2 wds. |
| 52% | SAMROCKWELL | 11 | "Three Billboards Outside Ebbing, Missouri" Oscar winner who played the title choreographer in 45-Across: 2 wds. |
| 52% | VIOLADAVIS | 10 | "The Help" Best Actress Oscar nominee who plays Veronica Rawlins in "Widows" (2 wds.) |
| 52% | MARLONBRANDO | 12 | Two-time Oscar winner who portrayed the rogue colonel in 31-Across: 2 wds |
| 51% | JAMIEFOXX | 9 | Oscar winner who plays jazz pianist Joe Gardner in 1-Across (2 wds.) |
| 50% | MERYLSTREEP | 11 | "The Iron Lady" Oscar winner who plays Aunt March in 36-Across (2 wds.) |
| 50% | JULIANNEMOORE | 13 | "Still Alice" Oscar winner who plays 50-Across in a 2020 biopic (2 wds.) |
| 50% | SIDNEYPOITIER | 13 | "Lilies of the Field" Oscar winner who played Donald Crease in "Sneakers": 2 wds. |
| 50% | GEORGECLOONEY | 13 | Two-time Oscar winner who starred with 44-Across in "Gravity" (2 wds.) |
| 50% | ALPACINO | 8 | "Scent of a Woman" Oscar winner who plays Hollywood producer/agent Marvin Schwartz in "Once Upon a Time in Hollywood" (2 wds.) |
| 50% | MICHAELDOUGLAS | 14 | "Wall Street" Best Actor Oscar winner who plays Hank Pym in the Marvel Cinematic Universe (2 wds.) |
| 50% | CATEBLANCHETT | 13 | Two-time Oscar winner who starred with 44-Across in "Ocean's 8" (2 wds.) |
| 48% | FORESTWHITAKER | 14 | "The Last King of Scotland" Best Actor Oscar winner who plays Zuri in the MCU (2 wds.) |
| 48% | TIMOTHYHUTTON | 13 | "Ordinary People" Oscar winner who plays the father of 50-Across in a 2020 biopic (2 wds.) |
| 48% | JESSICALANGE | 12 | Two-time Oscar-winning actress who starred in the 1976 movie "King Kong": 2 wds. |
| 48% | NAOMIWATTS | 10 | Two-time Oscar-nominated actress who starred in the 2005 movie "King Kong": 2 wds. |
| 48% | ROBINWILLIAMS | 13 | "Good Will Hunting" Oscar winner who plays the title nanny in "Mrs. Doubtfire" (2 wds.) |
| 48% | SANDRABULLOCK | 13 | Best Actress Oscar winner for "The Blind Side" who was a Worst Actress Razzie winner for "All About Steve": 2 wds. |
| 48% | SAMROCKWELL | 11 | "Three Billboards Outside Ebbing, Missouri" Oscar winner who plays a jaded London police inspector in 31-Across (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% | DIANNEWIEST | 11 | Best Supporting Actress Oscar winner in Woody Allen's "Bullets Over Broadway": 2 wds. |