| 100% | MAHERSHALAALI | 13 | "Hidden Figures" actor who won the 2017 and 2019 Oscars for Best Supporting Actor ("Moonlight" and "Green Book"): 2 wds. |
| 55% | CHRISTIANBALE | 13 | He won the Oscar and Golden Globe for Best Supporting Actor for 18-Across: 2 wds. |
| 54% | JOELGREY | 8 | "Wicked" actor who won the Best Supporting Actor Oscar for 1972's "Cabaret": 2 wds. |
| 53% | DANIELKALUUYA | 13 | "Judas and the Black Messiah" actor who won the 2020 Golden Globe Award for Best Supporting Actor - Motion Picture (2 wds.) |
| 52% | MARKRYLANCE | 11 | "Dunkirk" actor who won the 2016 Oscar for Best Supporting Actor ("Bridge of Spies"): 2 wds. |
| 51% | SAMROCKWELL | 11 | "Vice" actor who won the 2018 Oscar for Best Supporting Actor ("Three Billboards Outside Ebbing, Missouri"): 2 wds. |
| 51% | GREENBOOK | 9 | Film for which 32-Across won the Best Supporting Actor Oscar in 2019: 2 wds. |
| 50% | RAMIMALEK | 9 | Actor who became the first one of Egyptian heritage to win an Oscar for Best Actor in 2019: 2 wds. |
| 50% | JASONROBARDS | 12 | He won two Best Supporting Actor Oscars, for "All the President's Men" and "Julia": 2 wds. |
| 49% | RAMIMALEK | 9 | American actor who won the 2019 Golden Globe Award for Best Actor for the film "Bohemian Rhapsody": 2 wds. |
| 49% | MAHERSHALAALI | 13 | Best Supporting Actor Oscar winner for the 2018 film "Green Book": 2 wds. |
| 49% | MELISSALEO | 10 | She won the Oscar and Golden Globe for Best Supporting Actress for 18-Across: 2 wds. |
| 49% | JACKNICHOLSON | 13 | Actor who won three Oscars, for "One Flew Over the Cuckoo's Nest," "Terms of Endearment," and "As Good as It Gets": 2 wds. |
| 48% | JOELGREY | 8 | Singer/actor who won a Best Supporting Actor Oscar for playing the Master of Ceremonies in the 1972 film "Cabaret" (2 wds.) |
| 48% | JENNIFERHUDSON | 14 | Singer who won the Oscar for Best Performance in a Supporting Role for "Dreamgirls": 2 wds. |
| 48% | CUBAGOODINGJR | 13 | Actor who won a Best Supporting Actor Oscar for his role in the 1996 film "Jerry Maguire" (3 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% | GEOFFREYRUSH | 12 | Australian actor who won the Best Actor Oscar for 1996's "Shine": 2 wds. |
| 47% | MICHAELCAINE | 12 | He won two Best Supporting Actor Oscars, for "Hannah and Her Sisters" and "The Cider House Rules": 2 wds. |
| 47% | JUSTINHURWITZ | 13 | American composer who won the 2017 Oscar for Best Original Score for the film "La La Land": 2 wds. |
| 47% | JACKPALANCE | 11 | Actor who won a Best Supporting Actor Oscar for his 12-minute performance in "City Slickers" (2 wds.) |
| 46% | YULBRYNNER | 10 | Actor who won a Tony and an Oscar for playing King Mongkut in "The King and I": 2 wds. |
| 46% | ALI | 3 | Mahershala ___, actor who won the 2019 Golden Globe Award for Best Supporting Actor for the film in 16a |
| 46% | ANNAPAQUIN | 10 | 11-year-old who won the Oscar for Best Supporting Actress for "The Piano" in 1994: 2 wds. |
| 46% | TATUMONEAL | 10 | 10-year-old who won the Oscar for Best Supporting Actress for "Paper Moon" in 1974: 2 wds. |
| 46% | BRADPITT | 8 | Best Supporting Actor Oscar winner for the 2019 film "Once Upon a Time in Hollywood": 2 wds. |
| 45% | CLINTEASTWOOD | 13 | Actor and filmmaker who won an Oscar for Best Director at 74 for "Million Dollar Baby": 2 wds. |
| 45% | VIOLADAVIS | 10 | She won the 2017 Oscar for Best Supporting Actress for her role in "Fences": 2 wds. |
| 44% | SEANCONNERY | 11 | Actor born in Scotland who won the Academy Award for Best Supporting Actor for playing Jimmy Malone in "The Untouchables": 2 wds. |
| 44% | ARKIN | 5 | Alan who won the Best Supporting Actor Oscar for "Little Miss Sunshine" |