| 100% | GREENBOOK | 9 | Film for which 32-Across won the Best Supporting Actor Oscar in 2019: 2 wds. |
| 78% | MOONLIGHT | 9 | Film for which 32-Across won the Best Supporting Actor Oscar in 2017 |
| 68% | BRADPITT | 8 | Best Supporting Actor Oscar winner for the 2019 film "Once Upon a Time in Hollywood": 2 wds. |
| 64% | LILIESOF | 8 | With 44-Across, film for which 30-Across won the Oscar for Best Actor: 2 wds. |
| 62% | GREENBOOK | 9 | 2018 film for which 47-Across won a Best Supporting Actor Oscar (2 wds.) |
| 62% | THEHELP | 7 | 2011 film for which Octavia Spencer won the Oscar for Best Supporting Actress: 2 wds. |
| 61% | JOELGREY | 8 | Singer/actor who won a Best Supporting Actor Oscar for playing the Master of Ceremonies in the 1972 film "Cabaret" (2 wds.) |
| 60% | CUBAGOODINGJR | 13 | Actor who won a Best Supporting Actor Oscar for his role in the 1996 film "Jerry Maguire" (3 wds.) |
| 58% | MAHERSHALAALI | 13 | Best Supporting Actor Oscar winner for the 2018 film "Green Book": 2 wds. |
| 57% | REGINAKING | 10 | She won the 2019 Oscar for Best Supporting Actress for her role in "If Beale Street Could Talk": 2 wds. |
| 57% | JOELGREY | 8 | "Wicked" actor who won the Best Supporting Actor Oscar for 1972's "Cabaret": 2 wds. |
| 56% | TOMHANKS | 8 | Best Supporting Actor nominee for 2019's "A Beautiful Day in the Neighborhood": 2 wds. |
| 55% | MIGHTYAPHRODITE | 15 | Film for which Mira Sorvino won the Best Supporting Actress Oscar |
| 55% | 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.) |
| 55% | JASONROBARDS | 12 | He won two Best Supporting Actor Oscars, for "All the President's Men" and "Julia": 2 wds. |
| 55% | 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. |
| 55% | LAURADERN | 9 | Best Supporting Actress Oscar winner for the 2019 film "Marriage Story": 2 wds. |
| 54% | CATEBLANCHETT | 13 | Actress who won a Best Supporting Actress Oscar for playing Katharine Hepburn in the 2004 film "The Aviator" (2 wds.) |
| 53% | MOONLIGHT | 9 | 2016 film for which 47-Across won a Best Supporting Actor Oscar |
| 53% | THEGRADUATE | 11 | 1967 film for which 18-Across won his Best Director Oscar: 2 wds. |
| 53% | JENNIFERHUDSON | 14 | Singer who won the Oscar for Best Performance in a Supporting Role for "Dreamgirls": 2 wds. |
| 53% | GILBERTGRAPE | 12 | "What's Eating ___," film for which Leonardo DiCaprio (birthday today) received an Oscar nomination for best actor in a supporting role: 2 wds. |
| 53% | DARKESTHOUR | 11 | A 2017 war drama film for which actor Gary Oldman (birthday today) won the Academy Award for Best Actor: 2 wds. |
| 53% | ALBERTFINNEY | 12 | Best Supporting Actor Oscar nominee for 32-Across (2 wds.) |
| 52% | VIVAVILLA | 9 | 1934 movie for which Wallace Beery won the best actor award at the 2nd Venice Film Festival: 2 wds. |
| 52% | ALLISONJANNEY | 13 | She won the 2018 Oscar for Best Supporting Actress for her role in "I, Tonya": 2 wds. |
| 52% | IVES | 4 | Burl who won the Best Supporting Actor Oscar for his role as Rufus in "The Big Country" |
| 52% | CHAMP | 5 | The —, 1931 film for which Wallace Beery won a Best Actor in a Leading Role Oscar |
| 51% | JACKPALANCE | 11 | Actor who won a Best Supporting Actor Oscar for his 12-minute performance in "City Slickers" (2 wds.) |
| 51% | UNFORGIVEN | 10 | 1992 Clint Eastwood western for which Gene Hackman won the Best Supporting Actor Oscar |