| 100% | JULIEANDREWS | 12 | Actress who won an Oscar for playing the title role in 39-Across: 2 wds. |
| 85% | JULIEANDREWS | 12 | "The Sound of Music" actress who won an Oscar for playing the title role in 40-Across (2 wds.) |
| 77% | JULIEANDREWS | 12 | Actress who won an Oscar for playing the title nanny in "Mary Poppins" (2 wds.) |
| 63% | 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 her first feature film role, in "Mary Poppins": 2 wds. |
| 61% | LUPITANYONGO | 12 | Actress who won an Oscar for her first feature film role, in "12 Years a Slave": 2 wds. |
| 61% | LUPITANYONGO | 12 | Mexico-born actress who won an Oscar for her role in "12 Years a Slave": 2 wds. |
| 59% | CHRISTIANBALE | 13 | "American Hustle" actor who won an Oscar for his role in 48-Across' "The Fighter": 2 wds. |
| 56% | EDMUNDGWENN | 11 | "Mister 880" actor who won an Oscar for playing Kris Kringle in the 1947 Christmas classic "Miracle on 34th Street" (2 wds.) |
| 56% | JULIANNEMOORE | 13 | 18-Across actress who won an Oscar for 39-Across (2 wds.) |
| 56% | ANNEBANCROFT | 12 | Actress who won a Tony and an Oscar for playing Helen Keller's teacher in "The Miracle Worker": 2 wds. |
| 55% | LOUISEFLETCHER | 14 | Actress who won a Best Actress Oscar for playing 46-Across in the 1975 film "One Flew Over the Cuckoo's Nest" (2 wds.) |
| 55% | ANTHONYQUINN | 12 | Mexico-born actor who won an Oscar for his role in "Viva Zapata!": 2 wds. |
| 55% | RENEEZELLWEGER | 14 | Actress who won the Academy Award for Best Actress in 2020 for playing the title role in "Judy" (2 wds.) |
| 54% | VIOLADAVIS | 10 | Actress who won a Tony and an Oscar for playing Rose Maxson in "Fences": 2 wds. |
| 54% | SEANPENN | 8 | Actor who won an Oscar for playing Harvey Milk in "Milk" (2 wds.) |
| 53% | CATEBLANCHETT | 13 | Actress who won a Best Supporting Actress Oscar for playing Katharine Hepburn in the 2004 film "The Aviator" (2 wds.) |
| 53% | JULIEANDREWS | 12 | Performer who won an Academy Award for Best Actress for playing the title character in her film debut, "Mary Poppins" (2 wds.) |
| 52% | HOLLYHUNTER | 11 | "Broadcast News" star who won a Best Actress Oscar for her role in "The Piano": 2 wds. |
| 52% | MARLONBRANDO | 12 | "On the Waterfront" actor who won an Oscar for portraying 40-Across in 1972's "The Godfather": 2 wds. |
| 52% | 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. |
| 52% | JOANCRAWFORD | 12 | Actress who won an Oscar for 1945's "Mildred Pierce": 2 wds. |
| 52% | OLIVIAMUNN | 10 | "The Predator" actress who plays the title role in "Violet": 2 wds. |
| 51% | ALLISONJANNEY | 13 | Actress who won an Oscar for "I, Tonya" and an Emmy for "Mom": 2 wds. |
| 51% | JULIANNEMOORE | 13 | Redheaded actress who won an Oscar for "Still Alice": 2 wds. |
| 51% | GINARODRIGUEZ | 13 | Actress who plays the title role on 15-Across: 2 wds. |
| 51% | JULIAROBERTS | 12 | "Pretty Woman" actress who played the title role in 2000's "Erin Brockovich": 2 wds. |
| 51% | DERN | 4 | Actress who won an Oscar for her supporting role in 2019’s “Marriage Story” |
| 51% | 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. |
| 51% | JOAQUINPHOENIX | 14 | Actor who won an Oscar playing the Joker in 2019's "Joker," 11 years after Heath Ledger did the same: 2 wds. |