| 100% | JOELGREY | 8 | Singer/actor who won a Best Supporting Actor Oscar for playing the Master of Ceremonies in the 1972 film "Cabaret" (2 wds.) |
| 59% | CATEBLANCHETT | 13 | Actress who won a Best Supporting Actress Oscar for playing Katharine Hepburn in the 2004 film "The Aviator" (2 wds.) |
| 58% | CUBAGOODINGJR | 13 | Actor who won a Best Supporting Actor Oscar for his role in the 1996 film "Jerry Maguire" (3 wds.) |
| 55% | JOELGREY | 8 | "Wicked" actor who won the Best Supporting Actor Oscar for 1972's "Cabaret": 2 wds. |
| 54% | TIMOTHYHUTTON | 13 | Actor who won a Best Supporting Actor Oscar for his first role in a feature film (Conrad Jarrett in 1980's "Ordinary People") (2 wds.) |
| 52% | JACKPALANCE | 11 | Actor who won a Best Supporting Actor Oscar for his 12-minute performance in "City Slickers" (2 wds.) |
| 51% | WHOOPIGOLDBERG | 14 | Actress who won a Best Supporting Actress Oscar for playing 19-Across in 62-Across (2 wds.) |
| 51% | JENNIFERHUDSON | 14 | Singer who won the Oscar for Best Performance in a Supporting Role for "Dreamgirls": 2 wds. |
| 51% | BRADPITT | 8 | Best Supporting Actor Oscar winner for the 2019 film "Once Upon a Time in Hollywood": 2 wds. |
| 50% | JEREMYSTRONG | 12 | "Succession" actor who won the 2024 Best Leading Actor in a Play Tony for "An Enemy of the People": 2 wds. |
| 50% | YULBRYNNER | 10 | Actor who won a Tony and an Oscar for playing King Mongkut in "The King and I": 2 wds. |
| 50% | LIZAMINNELLI | 12 | Singer/actress who won a Best Actress Oscar for playing Sally Bowles in "Cabaret" (2 wds.) |
| 49% | INGRIDBERGMAN | 13 | Actress who won a Best Supporting Actress Oscar for her 14-minute performance in "Murder on the Orient Express" (2 wds.) |
| 49% | GREENBOOK | 9 | Film for which 32-Across won the Best Supporting Actor Oscar in 2019: 2 wds. |
| 48% | 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.) |
| 48% | SEANCONNERY | 11 | Actor born in Scotland who won the Academy Award for Best Supporting Actor for playing Jimmy Malone in "The Untouchables": 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% | WESTSIDESTORY | 13 | 1961 film starring Rita Moreno, who won a Best Supporting Actress Oscar for playing Anita (3 wds.) |
| 48% | MARKRYLANCE | 11 | "Dunkirk" actor who won the 2016 Oscar for Best Supporting Actor ("Bridge of Spies"): 2 wds. |
| 47% | KODISMITMCPHEE | 14 | "The Power of the Dog" co-star who won a Golden Globe Award for Best Supporting Actor - Motion Picture in 2022 (2 wds.) |
| 47% | LUPITANYONGO | 12 | Actress who won a Best Supporting Actress Oscar for her first role in a feature film (Patsey in 2013's "12 Years a Slave") (2 wds.) |
| 47% | CHRISTIANBALE | 13 | Actor who won the 2019 Golden Globe Award for Best Actor in a Motion Picture - Musical or Comedy, for the film "Vice": 2 wds. |
| 47% | RAMIMALEK | 9 | Actor who became the first one of Egyptian heritage to win an Oscar for Best Actor in 2019: 2 wds. |
| 46% | COLINFARRELL | 12 | Best Actor Oscar nominee for his portrayal of a man who is suddenly cut out of the life of his best friend in the 2022 film "The Banshees of Inisherin" (2 wds.) |
| 45% | SHELLEYWINTERS | 14 | "A Patch of Blue" and "The Diary of Anne Frank" Oscar winner who was nominated for an Oscar for playing the swimmer Belle Rosen in the 1972 film "The Poseidon Adventure" (2 wds.) |
| 45% | EDDIEREDMAYNE | 13 | "The Theory of Everything" actor who was nominated for a 2024 Tony for playing the Emcee in "Cabaret": 2 wds. |
| 45% | 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. |
| 45% | BRYANCRANSTON | 13 | "Breaking Bad" actor who won two Tony Awards for Best Actor in a Play, for "All the Way" and "Network" (2 wds.) |
| 44% | ANNEBANCROFT | 12 | Actress who won a Tony and an Oscar for playing Helen Keller's teacher in "The Miracle Worker": 2 wds. |
| 44% | CHRISTIANBALE | 13 | Actor born in Wales who won the Academy Award for Best Supporting Actor for playing Dick Dicky Eklund in the movie "The Fighter": 2 wds |