| 100% | RACHELMCADAMS | 13 | "Spotlight" Best Supporting Actress Oscar nominee who co-stars in 14-Across, 25-Across, and 35-Across (2 wds.) |
| 50% | MICHAELSHANNON | 14 | Two-time Best Supporting Actor Oscar nominee who plays Nicky in 46-Across (2 wds.) |
| 49% | KATHARINEROSS | 13 | Best Supporting Actress Oscar nominee for playing Elaine Robinson in 28-Across (2 wds.) |
| 49% | SANDRABULLOCK | 13 | "The Blind Side" Best Actress Oscar winner who starred in 15-Across, 24-Across, 31-Across, and 40-Across (2 wds.) |
| 49% | INGRIDBERGMAN | 13 | Actress who won a Best Supporting Actress Oscar for her 14-minute performance in "Murder on the Orient Express" (2 wds.) |
| 48% | WHOOPIGOLDBERG | 14 | Actress who won a Best Supporting Actress Oscar for playing 19-Across in 62-Across (2 wds.) |
| 48% | SAOIRSERONAN | 12 | "Brooklyn," "Lady Bird," and "Little Women" Best Actress Oscar nominee who was nominated for Best Supporting Actress for "Atonement" (2 wds.) |
| 48% | ABOUTSCHMIDT | 12 | 2002 dramedy starring Kathy Bates, who was nominated for a Best Supporting Actress Oscar for playing a woman in a memorable hot tub scene (2 wds.) |
| 47% | ANGELINAJOLIE | 13 | "Girl, Interrupted" Best Supporting Actress Oscar winner who plays Thena in Marvel's "Eternals" (2 wds.) |
| 46% | LUPITANYONGO | 12 | "12 Years a Slave" Best Supporting Actress Oscar winner who plays Nakia in Marvel's "Black Panther" (2 wds.) |
| 46% | TILDASWINTON | 12 | "Michael Clayton" Best Supporting Actress Oscar winner who plays The Ancient One in Marvel's "Doctor Strange" (2 wds.) |
| 45% | DIANELADD | 9 | Best Supporting Actress Oscar nominee for 29-Across (2 wds.) |
| 45% | CATEBLANCHETT | 13 | Actress who won a Best Supporting Actress Oscar for playing Katharine Hepburn in the 2004 film "The Aviator" (2 wds.) |
| 44% | ANNAPAQUIN | 10 | 11-year-old who won the Oscar for Best Supporting Actress for "The Piano" in 1994: 2 wds. |
| 44% | TATUMONEAL | 10 | 10-year-old who won the Oscar for Best Supporting Actress for "Paper Moon" in 1974: 2 wds. |
| 44% | VIOLADAVIS | 10 | "The Help" Best Actress Oscar nominee who plays Veronica Rawlins in "Widows" (2 wds.) |
| 44% | KIMBASINGER | 11 | Actress who won a Best Supporting Actress Oscar for her 15-minute performance in "L.A. Confidential" (2 wds.) |
| 44% | CYNTHIAERIVO | 12 | Nominee for the Best Actress and Best Original Song Oscars for her work in "Harriet": 2 wds. |
| 44% | RYANGOSLING | 11 | "Barbie" actor who stars in 15-Across, 35-Across, and 43-Across (2 wds.) |
| 43% | MARGOTROBBIE | 12 | "I, Tonya" Best Actress Oscar nominee who was nominated for Best Supporting Actress for "Bombshell" (2 wds.) |
| 43% | HOLLYHUNTER | 11 | "Broadcast News" star who won a Best Actress Oscar for her role in "The Piano": 2 wds. |
| 43% | RITAMORENO | 10 | Actress who attended the 2018 Oscars in the same dress she wore to the 1962 Oscars, when she won Best Supporting Actress: 2 wds. |
| 43% | SAOIRSERONAN | 12 | Oscar nominee who co-stars with Meryl Streep in "Little Women" (2 wds.) |
| 43% | SALLYHAWKINS | 12 | "The Shape of Water" Best Actress Oscar nominee who was nominated for Best Supporting Actress for "Blue Jasmine" (2 wds.) |
| 43% | ANGELINAJOLIE | 13 | Actress who stars in, wrote, directed, and coproduced 16-Across: 2 wds. |
| 43% | CHARLIZETHERON | 14 | 15-Across and 29-Across star who won a Best Actress Oscar for "Monster" and who turns 45 today (2 wds.) |
| 43% | RYANGOSLING | 11 | Actor born November 12, 1980, who stars in 15-Across, 35-Across, and 43-Across (2 wds.) |
| 43% | LUPITANYONGO | 12 | Actress who won a Best Supporting Actress Oscar for her first role in a feature film (Patsey in 2013's "12 Years a Slave") (2 wds.) |
| 43% | MIRASORVINO | 11 | Best Supporting Actress Oscar winner in Woody Allen's "Mighty Aphrodite": 2 wds. |
| 43% | BRYANCRANSTON | 13 | "Trumbo" Best Actor Oscar nominee who voices Chief in 43-Across (2 wds.) |