| 100% | MORGANFREEMAN | 13 | Actor in the Best Picture Oscar films "Driving Miss Daisy," "Unforgiven," and "Million Dollar Baby": 2 wds. |
| 60% | COLINFIRTH | 10 | Actor in the Best Picture Oscar films "The English Patient," "Shakespeare in Love," and "The King's Speech": 2 wds. |
| 59% | CLARKGABLE | 10 | Actor in the Best Picture Oscar films "It Happened One Night," "Mutiny on the Bounty," and "Gone With the Wind": 2 wds. |
| 43% | RICHARDHARRIS | 13 | Actor in the Best Picture winner "Unforgiven" who was nominated for an Album of the Year Grammy in 1968: 2 wds. |
| 41% | MORGANFREEMAN | 13 | "Million Dollar Baby" actor who received the SAG Life Achievement Award in 2017: 2 wds. |
| 40% | CLINTEASTWOOD | 13 | "Million Dollar Baby" and "Unforgiven" actor/director: 2 wds. |
| 40% | FRANKSINATRA | 12 | Actor in the Best Picture winner "From Here to Eternity" who was nominated for seven Album of the Year Grammys: 2 wds. |
| 39% | PULPFICTION | 11 | Best Picture Oscar nominee directed by Quentin Tarantino that won the Palme d'Or at the Cannes Film Festival in 1994 (2 wds.) |
| 39% | APOCALYPSENOW | 13 | Best Picture Oscar nominee directed by Francis Ford Coppola that won the Palme d'Or at the Cannes Film Festival in 1979 (2 wds.) |
| 38% | THEKINGSSPEECH | 14 | 2010 historical drama about George VI that won both the Best Picture Oscar and the Best Film BAFTA: 3 wds. |
| 38% | CHARIOTSOFFIRE | 14 | 1981 historical drama about Olympic runners that won both the Best Picture Oscar and the Best Film BAFTA: 3 wds. |
| 38% | GREENBOOK | 9 | Film for which 32-Across won the Best Supporting Actor Oscar in 2019: 2 wds. |
| 38% | NICHOLSON | 9 | Actor in the Best Picture winners of 1975, 1983 and 2006 |
| 37% | CLINTEASTWOOD | 13 | Actor and filmmaker who won an Oscar for Best Director at 74 for "Million Dollar Baby": 2 wds. |
| 37% | CYNTHIAERIVO | 12 | Nominee for the Best Actress and Best Original Song Oscars for her work in "Harriet": 2 wds. |
| 37% | SCHINDLERSLIST | 14 | 1993 historical drama about the Holocaust that won both the Best Picture Oscar and the Best Film BAFTA: 2 wds. |
| 37% | ALLTHATJAZZ | 11 | Best Picture Oscar nominee directed by Bob Fosse that won the Palme d'Or at the Cannes Film Festival in 1980 (3 wds.) |
| 36% | EASTWOOD | 8 | Clint —, Best Director Oscar winner for Unforgiven and Million Dollar Baby |
| 36% | CLINTEASTWOOD | 13 | Oldest person to win the Best Director Oscar, at 74 (for "Million Dollar Baby"): 2 wds. |
| 35% | LALA | 4 | "___ Land" (movie that lost the Best Picture Oscar to "Moonlight"): 2 wds. |
| 35% | LESLIEODOMJR | 12 | Nominee for the Best Supporting Actor and Best Original Song Oscars for his work in "One Night in Miami ...": 3 wds., abbr. |
| 35% | ERINBROCKOVICH | 14 | Best Picture Oscar nominee starring 19-Across as lawyer Ed Masry and 42-Across as the title activist (2 wds.) |
| 34% | CLINTEASTWOOD | 13 | "Million Dollar Baby" director who has won 2 Oscars out of 4 nominations for Best Director: 2 wds. |
| 34% | THEDEPARTED | 11 | Martin Scorsese film that won the Oscar for Best Picture in 2007 (2 wds.) |
| 34% | VIVIENLEIGH | 11 | Actress who played Scarlett O'Hara in the film "Gone With the Wind" and also won an Oscar for her work in the film: 2 wds. |
| 34% | HOLLYHUNTER | 11 | Best Actress Oscar winner for her role in the 1993 film "The Piano" (2 wds.) |
| 34% | JEFFREYWRIGHT | 13 | Actor in the 2021 movies "No Time to Die" and "The French Dispatch": 2 wds. |
| 34% | AUSTINBUTLER | 12 | Best Actor Oscar nominee for his portrayal of the "King of Rock and Roll" in the 2022 film "Elvis" (2 wds.) |
| 34% | JESSICATANDY | 12 | "Driving Miss Daisy" actress who played 15-Across in the original 1940s stage production of "A Streetcar Named Desire": 2 wds. |
| 33% | 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. |