| 100% | SAMROCKWELL | 11 | "Vice" actor who won the 2018 Oscar for Best Supporting Actor ("Three Billboards Outside Ebbing, Missouri"): 2 wds. |
| 61% | MARKRYLANCE | 11 | "Dunkirk" actor who won the 2016 Oscar for Best Supporting Actor ("Bridge of Spies"): 2 wds. |
| 54% | JOELGREY | 8 | "Wicked" actor who won the Best Supporting Actor Oscar for 1972's "Cabaret": 2 wds. |
| 53% | MAHERSHALAALI | 13 | "Hidden Figures" actor who won the 2017 and 2019 Oscars for Best Supporting Actor ("Moonlight" and "Green Book"): 2 wds. |
| 52% | ALLISONJANNEY | 13 | She won the 2018 Oscar for Best Supporting Actress for her role in "I, Tonya": 2 wds. |
| 52% | 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. |
| 52% | SEANCONNERY | 11 | Actor born in Scotland who won the Academy Award for Best Supporting Actor for playing Jimmy Malone in "The Untouchables": 2 wds. |
| 51% | SAMROCKWELL | 11 | "Three Billboards Outside Ebbing, Missouri" Oscar winner who played the title choreographer in 45-Across: 2 wds. |
| 51% | 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 |
| 49% | GEOFFREYRUSH | 12 | Australian actor who won the Best Actor Oscar for 1996's "Shine": 2 wds. |
| 49% | MAHERSHALAALI | 13 | Best Supporting Actor Oscar winner for the 2018 film "Green Book": 2 wds. |
| 48% | SAMROCKWELL | 11 | "Three Billboards Outside Ebbing, Missouri" actor who voices the title gorilla in "The One and Only Ivan" (2 wds.) |
| 48% | JAREDLETO | 9 | Onetime teen idol who went on to win the 2013 Oscar for Best Supporting Actor |
| 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.) |
| 47% | ANNAPAQUIN | 10 | 11-year-old who won the Oscar for Best Supporting Actress for "The Piano" in 1994: 2 wds. |
| 47% | TATUMONEAL | 10 | 10-year-old who won the Oscar for Best Supporting Actress for "Paper Moon" in 1974: 2 wds. |
| 47% | CHRISTIANBALE | 13 | He won the Oscar and Golden Globe for Best Supporting Actor for 18-Across: 2 wds. |
| 47% | JENNIFERHUDSON | 14 | Singer who won the Oscar for Best Performance in a Supporting Role for "Dreamgirls": 2 wds. |
| 47% | VIOLADAVIS | 10 | She won the 2017 Oscar for Best Supporting Actress for her role in "Fences": 2 wds. |
| 47% | CUBAGOODINGJR | 13 | Actor who won a Best Supporting Actor Oscar for his role in the 1996 film "Jerry Maguire" (3 wds.) |
| 47% | JASONROBARDS | 12 | He won two Best Supporting Actor Oscars, for "All the President's Men" and "Julia": 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. |
| 47% | SAMROCKWELL | 11 | "Three Billboards Outside Ebbing, Missouri" actor who plays George W. Bush in "Vice" (2 wds.) |
| 46% | GREENBOOK | 9 | Film for which 32-Across won the Best Supporting Actor Oscar in 2019: 2 wds. |
| 46% | RITAMORENO | 10 | Actress who attended the 2018 Oscars in the same dress she wore to the 1962 Oscars, when she won Best Supporting Actress: 2 wds. |
| 45% | JACKNICHOLSON | 13 | "The Shining" actor who has won two oscars, one of them for "As Good as it Gets": 2 wds |
| 45% | JACKPALANCE | 11 | Actor who won a Best Supporting Actor Oscar for his 12-minute performance in "City Slickers" (2 wds.) |
| 45% | JUSTINHURWITZ | 13 | American composer who won the 2017 Oscar for Best Original Score for the film "La La Land": 2 wds. |
| 45% | FRANCES | 7 | McDormand who won an Oscar for "Three Billboards Outside Ebbing, Missouri" |
| 45% | REGINAKING | 10 | She won the 2019 Oscar for Best Supporting Actress for her role in "If Beale Street Could Talk": 2 wds. |