| 100% | JACKPALANCE | 11 | He won an Oscar playing trail boss Curly Washburn in the 1991 comedy "City Slickers": 2 wds. |
| 40% | JULIEANDREWS | 12 | Actress who won an Oscar for playing the title role in 39-Across: 2 wds. |
| 40% | JOAQUINPHOENIX | 14 | Actor who won an Oscar playing the Joker in 2019's "Joker," 11 years after Heath Ledger did the same: 2 wds. |
| 38% | JULIEANDREWS | 12 | Actress who won an Oscar for playing the title nanny in "Mary Poppins" (2 wds.) |
| 37% | JACKPALANCE | 11 | "City Slickers" Oscar winner who plays twin brothers Curly and Duke Washburn in the "City Slickers" films (2 wds.) |
| 36% | EDMUNDGWENN | 11 | "Mister 880" actor who won an Oscar for playing Kris Kringle in the 1947 Christmas classic "Miracle on 34th Street" (2 wds.) |
| 35% | JULIEANDREWS | 12 | "The Sound of Music" actress who won an Oscar for playing the title role in 40-Across (2 wds.) |
| 34% | MERYLSTREEP | 11 | Actress nominated for an Oscar for playing a music teacher in "Music of the Heart": 2 wds. |
| 34% | JAMIEFOXX | 9 | He won an Oscar for playing Ray Charles in 2004 |
| 33% | SEANPENN | 8 | Actor who won an Oscar for playing Harvey Milk in "Milk" (2 wds.) |
| 33% | 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. |
| 33% | CHRISTIANBALE | 13 | "American Hustle" actor who won an Oscar for his role in 48-Across' "The Fighter": 2 wds. |
| 32% | CHEVYCHASE | 10 | He played Clark Griswold in the 1983 comedy "National Lampoon's Vacation": 2 wds. |
| 32% | THEFAVOURITE | 12 | 2018 movie for which 13-Across won an Oscar playing Queen Anne: 2 wds. |
| 31% | BENKINGSLEY | 11 | Actor whose birthday it is today who won an Academy Award for playing Gandhi in the titular film and was knighted in 2002: 2 wds. |
| 31% | YULBRYNNER | 10 | Actor who won a Tony and an Oscar for playing King Mongkut in "The King and I": 2 wds. |
| 30% | SAMSMITH | 8 | Nonbinary singer who won an Oscar for the Bond theme "Writing's on the Wall": 2 wds. |
| 30% | LUPITANYONGO | 12 | Mexico-born actress who won an Oscar for her role in "12 Years a Slave": 2 wds. |
| 30% | JOHNLEGEND | 10 | Artist on "Songland" whose "Glory," with Common, won an Oscar for Best Song in 2015: 2 wds. |
| 30% | SIDNEYPOITIER | 13 | Star of 15- and 34-Across who won an Oscar for "Lilies of the Field": 2 wds. |
| 30% | ANTHONYQUINN | 12 | Mexico-born actor who won an Oscar for his role in "Viva Zapata!": 2 wds. |
| 30% | GEORGESANDERS | 13 | Actor who won an Oscar as columnist Addison DeWitt in "All About Eve": 2 wds. |
| 30% | JENNIFERHUDSON | 14 | Actress who won an Oscar for her first feature film role, in "Dreamgirls": 2 wds. |
| 30% | JAMIEFOXX | 9 | Actor who won an Oscar for portraying Ray Charles in a 2004 biopic: 2 wds. |
| 30% | BILLYCRYSTAL | 12 | He played account executive Mitch Robbins in "City Slickers": 2 wds. |
| 30% | MARLONBRANDO | 12 | "On the Waterfront" actor who won an Oscar for portraying 40-Across in 1972's "The Godfather": 2 wds. |
| 30% | JULIEANDREWS | 12 | Actress who won an Oscar for her first feature film role, in "Mary Poppins": 2 wds. |
| 30% | JASONROBARDS | 12 | He won two Best Supporting Actor Oscars, for "All the President's Men" and "Julia": 2 wds. |
| 29% | LUPITANYONGO | 12 | Actress who won an Oscar for her first feature film role, in "12 Years a Slave": 2 wds. |
| 29% | VIOLADAVIS | 10 | Actress who won a Tony and an Oscar for playing Rose Maxson in "Fences": 2 wds. |