| 100% | HILARYSWANK | 11 | Oscar-winning actress who plays boxer Maggie Fitzgerald in "Million Dollar Baby" (2 wds.) |
| 54% | JULIEANDREWS | 12 | Actress who won an Oscar for playing the title role in 39-Across: 2 wds. |
| 53% | HILARYSWANK | 11 | Actress who won her second Oscar, for 2004's "Million Dollar Baby," at age 30: 2 wds. |
| 53% | SUSANSARANDON | 13 | Oscar-winning actress who played Janet in "The Rocky Horror Picture Show": 2 wds. |
| 52% | HILARYSWANK | 11 | "Million Dollar Baby" actress who plays high-school teacher Erin Gruwell in "Freedom Writers" (2 wds.) |
| 52% | JULIEANDREWS | 12 | Oscar-winning actress who played Mary Poppins in the 1964 movie: 2 wds. |
| 52% | HILARYSWANK | 11 | "Million Dollar Baby" actress who plays a journalist whose son was murdered in 31-Across (2 wds.) |
| 51% | MORGANFREEMAN | 13 | Oscar-winning actor who plays gym assistant and former boxer Eddie "Scrap-Iron" Dupris in "Million Dollar Baby" (2 wds.) |
| 50% | EMMATHOMPSON | 12 | Oscar-winning actress who plays P.L. Travers, author of the novel "Mary Poppins," in 32-Across: 2 wds. |
| 50% | CLINTEASTWOOD | 13 | "Million Dollar Baby" director who has won 2 Oscars out of 4 nominations for Best Director: 2 wds. |
| 49% | WHOOPIGOLDBERG | 14 | Actress who won a Best Supporting Actress Oscar for playing 19-Across in 62-Across (2 wds.) |
| 49% | 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. |
| 49% | LILYJAMES | 9 | "Downton Abbey" actress who plays Deborah, Baby's girlfriend in "Baby Driver": 2 wds. |
| 49% | HILARYSWANK | 11 | "Million Dollar baby" actress who plays a hairdresser who rallies her town during a blizzard to help a critically ill girl in "Ordinary Angels" (2 wds.) |
| 48% | CATEBLANCHETT | 13 | Actress who won a Best Supporting Actress Oscar for playing Katharine Hepburn in the 2004 film "The Aviator" (2 wds.) |
| 48% | LIZAMINNELLI | 12 | Singer/actress who won a Best Actress Oscar for playing Sally Bowles in "Cabaret" (2 wds.) |
| 48% | JULIEANDREWS | 12 | "The Sound of Music" actress who won an Oscar for playing the title role in 40-Across (2 wds.) |
| 48% | DEBRAMESSING | 12 | Actress who played 17a in the series for which she won a Primetime Emmy Award: 2 wds. |
| 47% | VIOLADAVIS | 10 | Actress who won a Tony and an Oscar for playing Rose Maxson in "Fences": 2 wds. |
| 47% | HILARYSWANK | 11 | "Million Dollar Baby" actress who plays Eileen on 44-Across (2 wds.) |
| 47% | 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.) |
| 47% | CLINTEASTWOOD | 13 | Oscar-winning actor/director who plays gym owner and boxing trainer Frankie Dunn in "Million Dollar Baby" (2 wds.) |
| 46% | HELENMIRREN | 11 | Actress who won a Best Actress Oscar as Queen Elizabeth II in "The Queen": 2 wds. |
| 46% | JULIEANDREWS | 12 | Actress who won an Oscar for her first feature film role, in "Mary Poppins": 2 wds. |
| 46% | LUPITANYONGO | 12 | Actress who won an Oscar for her first feature film role, in "12 Years a Slave": 2 wds. |
| 45% | LUPITANYONGO | 12 | Mexico-born actress who won an Oscar for her role in "12 Years a Slave": 2 wds. |
| 45% | JULIEANDREWS | 12 | Actress who won an Oscar for playing the title nanny in "Mary Poppins" (2 wds.) |
| 45% | HILARYSWANK | 11 | "Million Dollar Baby" actress who dropped out of high school: 2 wds. |
| 45% | ANNEBANCROFT | 12 | Actress who won a Tony and an Oscar for playing Helen Keller's teacher in "The Miracle Worker": 2 wds. |
| 45% | LILYJAMES | 9 | "Baby Driver" actress who plays Pamela Anderson in Hulu's "Pam & Tommy": 2 wds. |