| 100% | JAMIEFOXX | 9 | Host of "Beat Shazam" who won an Oscar for "Ray" (2 wds.) |
| 95% | JAMIEFOXX | 9 | Host of "Beat Shazam" who won an Oscar for the film "Ray" (2 wds.) |
| 71% | JAMIEFOXX | 9 | Actor who won an Oscar for portraying Ray Charles in a 2004 biopic: 2 wds. |
| 69% | ANNEHATHAWAY | 12 | "Les Misérables" actress who won an Oscar for her performance, despite only 15 minutes of screen time: 2 wds. |
| 67% | ALLISONJANNEY | 13 | "I, Tonya" actress who won an Oscar for her performance, despite only 15 minutes and 37 seconds of screen time: 2 wds. |
| 67% | MARTINSCORSESE | 14 | New Hollywood director who won an Oscar for "The Departed," and is the most-nominated director alive in terms of Oscars: 2 wds. |
| 67% | PENELOPECRUZ | 12 | "Vicky Cristina Barcelona" actress who won an Oscar for her performance, despite only 14 minutes and 29 seconds of screen time: 2 wds. |
| 65% | JOANCRAWFORD | 12 | Actress who won an Oscar for 1945's "Mildred Pierce": 2 wds. |
| 64% | JULIANNEMOORE | 13 | Redheaded actress who won an Oscar for "Still Alice": 2 wds. |
| 64% | ALFONSOCUARON | 13 | Mexico-born director who won an Oscar for "Gravity": 2 wds. |
| 62% | ALLISONJANNEY | 13 | Actress who won an Oscar for "I, Tonya" and an Emmy for "Mom": 2 wds. |
| 62% | ANTHONYQUINN | 12 | Mexico-born actor who won an Oscar for his role in "Viva Zapata!": 2 wds. |
| 62% | JENNIFERHUDSON | 14 | Actress who won an Oscar for her first feature film role, in "Dreamgirls": 2 wds. |
| 62% | JULIEANDREWS | 12 | Actress who won an Oscar for playing the title role in 39-Across: 2 wds. |
| 62% | JULIEANDREWS | 12 | Actress who won an Oscar for her first feature film role, in "Mary Poppins": 2 wds. |
| 61% | CHRISTIANBALE | 13 | "American Hustle" actor who won an Oscar for his role in 48-Across' "The Fighter": 2 wds. |
| 61% | LUPITANYONGO | 12 | Mexico-born actress who won an Oscar for her role in "12 Years a Slave": 2 wds. |
| 61% | SAMSMITH | 8 | Nonbinary singer who won an Oscar for the Bond theme "Writing's on the Wall": 2 wds. |
| 61% | CLINTEASTWOOD | 13 | Actor and filmmaker who won an Oscar for Best Director at 74 for "Million Dollar Baby": 2 wds. |
| 61% | LUPITANYONGO | 12 | Actress who won an Oscar for her first feature film role, in "12 Years a Slave": 2 wds. |
| 61% | JULIANNEMOORE | 13 | 18-Across actress who won an Oscar for 39-Across (2 wds.) |
| 61% | DELTORO | 7 | Actor Benicio who won an Oscar for "Traffic" (2 wds.) |
| 60% | MARLONBRANDO | 12 | "On the Waterfront" actor who won an Oscar for portraying 40-Across in 1972's "The Godfather": 2 wds. |
| 60% | SIDNEYPOITIER | 13 | Star of 15- and 34-Across who won an Oscar for "Lilies of the Field": 2 wds. |
| 59% | JULIEANDREWS | 12 | "The Sound of Music" actress who won an Oscar for playing the title role in 40-Across (2 wds.) |
| 59% | SEANPENN | 8 | Actor who won an Oscar for playing Harvey Milk in "Milk" (2 wds.) |
| 59% | LIZAMINNELLI | 12 | Actress who won an Oscar for Best Actress for "Cabaret" and a Worst Actress Razzie Award for "Rent-a-Cop": 2 wds. |
| 58% | JULIEANDREWS | 12 | Actress who won an Oscar for playing the title nanny in "Mary Poppins" (2 wds.) |
| 58% | SANDRABULLOCK | 13 | Actress who won an Oscar for Best Actress for "The Blind Side" and a Worst Actress Razzie Award for "All About Steve": 2 wds. |
| 58% | RAMIMALEK | 9 | Actor who became the first one of Egyptian heritage to win an Oscar for Best Actor in 2019: 2 wds. |