| 100% | ARIANADEBOSE | 12 | "West Side Story" Oscar winner who voices Asha in "Wish" (2 wds.) |
| 66% | ARIANADEBOSE | 12 | "West Side Story" Oscar winner who hosted the Tony Awards in 2022, 2023, and 2024 (2 wds.) |
| 56% | CHARLIZETHERON | 14 | "Monster" Oscar winner who voices Morticia in "The Addams Family" (2 wds.) |
| 52% | JKSIMMONS | 9 | "Whiplash" Oscar winner who voices "Yellow" in M&M candy commercials: 3 wds. |
| 51% | CATEBLANCHETT | 13 | "Blue Jasmine" Oscar winner who stars in 18-Across: 2 wds. |
| 51% | MORENO | 6 | West Side Story Oscar winner |
| 50% | KEVINKLINE | 10 | "A Fish Called Wanda" Oscar winner who stars in 18-Across: 2 wds. |
| 50% | ARIANADEBOSE | 12 | "West Side Story" actress who plays Kraven's love interest, the priestess Calypso, in "Kraven the Hunter": 2 wds. |
| 50% | MARLONBRANDO | 12 | Two-time Oscar winner who portrayed the rogue colonel in 31-Across: 2 wds |
| 50% | SIDNEYPOITIER | 13 | "Lilies of the Field" Oscar winner who played Donald Crease in "Sneakers": 2 wds. |
| 50% | TIMALLEN | 8 | "Home Improvement" actor who voiced Buzz Lightyear in "Toy Story": 2 wds. |
| 50% | ANNIEPOTTS | 10 | "Designing Women" actress who voiced Bo Peep in "Toy Story": 2 wds. |
| 48% | SAMROCKWELL | 11 | "Three Billboards Outside Ebbing, Missouri" Oscar winner who played the title choreographer in 45-Across: 2 wds. |
| 48% | CHARLIZETHERON | 14 | "Monster" Oscar winner who was Harvard's Hasty Pudding Woman of the Year in 2008: 2 wds. |
| 48% | HELENMIRREN | 11 | "The Queen" Oscar winner who was honored with Lincoln Center's Chaplin Award in 2018: 2 wds. |
| 48% | CATEBLANCHETT | 13 | "Blue Jasmine" Oscar winner who was honored with Lincoln Center's Chaplin Award in 2022: 2 wds. |
| 48% | RAMIMALEK | 9 | "Bohemian Rhapsody" Oscar winner who was in the James Bond movie "No Time to Die": 2 wds. |
| 48% | OCTAVIASPENCER | 14 | "The Help" Oscar winner who was Harvard's Hasty Pudding Woman of the Year in 2017: 2 wds. |
| 48% | RENEEZELLWEGER | 14 | "Cold Mountain" Oscar winner who was Harvard's Hasty Pudding Woman of the Year in 2009: 2 wds. |
| 48% | MERYLSTREEP | 11 | "The Iron Lady" Oscar winner who was honored with Lincoln Center's Chaplin Award in 2008: 2 wds. |
| 48% | JOHNNYDEPP | 10 | Actor who voiced Rango, a heroic green chameleon in the Old West: 2 wds. |
| 48% | BRIELARSON | 10 | "Room" Oscar winner who plays Captain Marvel in Marvel films (2 wds.) |
| 48% | JONVOIGHT | 9 | "Coming Home" Oscar winner who played Ed Gentry in "Deliverance" (2 wds.) |
| 47% | DONRICKLES | 10 | "Kelly's Heroes" actor/comedian who voiced Mr. Potato Head in "Toy Story": 2 wds. |
| 47% | NICOLEKIDMAN | 12 | Oscar winner who co-stars with Meryl Streep in "The Hours" (2 wds.) |
| 47% | JAMIEFOXX | 9 | Oscar winner who plays jazz pianist Joe Gardner in 1-Across (2 wds.) |
| 47% | NICOLASCAGE | 11 | Oscar winner who stars in the 1998 film "City of Angels" (2 wds.) |
| 47% | OLIVIACOLMAN | 12 | Oscar winner who co-stars with Meryl Streep in "The Iron Lady" (2 wds.) |
| 46% | KELLYCLARKSON | 13 | "American Idol" winner who voices Delta Dawn in "Trolls World Tour" (2 wds.) |
| 46% | OLYMPIADUKAKIS | 14 | "Moonstruck" Oscar winner who starred in 16-Across and 34-Across (2 wds.) |