| 100% | SIDNEYPOITIER | 13 | Star of 15- and 34-Across who won an Oscar for "Lilies of the Field": 2 wds. |
| 71% | SIDNEYPOITIER | 13 | 15-Across, 30-Across, and "Lilies of the Field" star who was the first Black man to win an Academy Award for Best Actor (2 wds.) |
| 59% | ALLISONJANNEY | 13 | "I, Tonya" actress who won an Oscar for her performance, despite only 15 minutes and 37 seconds of screen time: 2 wds. |
| 59% | 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. |
| 59% | LORETTADEVINE | 13 | Star of 15-Across who won an Emmy for a guest performance in "Grey's Anatomy": 2 wds. |
| 55% | JULIEANDREWS | 12 | "The Sound of Music" actress who won an Oscar for playing the title role in 40-Across (2 wds.) |
| 55% | ANNEHATHAWAY | 12 | "Les Misérables" actress who won an Oscar for her performance, despite only 15 minutes of screen time: 2 wds. |
| 54% | TOBIASMENZIES | 13 | 15-Across and 30-Across actor who won an Emmy for playing Prince Philip, Duke of Edinburgh, on "The Crown" (2 wds.) |
| 54% | RAMIMALEK | 9 | Actor who became the first one of Egyptian heritage to win an Oscar for Best Actor in 2019: 2 wds. |
| 54% | JAMIEFOXX | 9 | Host of "Beat Shazam" who won an Oscar for the film "Ray" (2 wds.) |
| 53% | 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. |
| 53% | JULIEANDREWS | 12 | Actress who won an Oscar for playing the title role in 39-Across: 2 wds. |
| 53% | NICOLEKIDMAN | 12 | "Moulin Rouge!" and "The Hours" star who was the first Australian to win an Oscar for Best Actress and the first to be nominated in consecutive years (2 wds.) |
| 52% | JODIEFOSTER | 11 | Actress who won a Golden Globe and an Oscar for both "The Accused" and "The Silence of the Lambs" (2 wds.) |
| 52% | MARLONBRANDO | 12 | "On the Waterfront" actor who won an Oscar for portraying 40-Across in 1972's "The Godfather": 2 wds. |
| 51% | ROBERTDUVALL | 12 | "The Godfather" costar who starred as Mac Sledge in 28-Across, for which he won an Oscar: 2 wds. |
| 51% | 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. |
| 51% | JACKNICHOLSON | 13 | Actor who won three Oscars, for "One Flew Over the Cuckoo's Nest," "Terms of Endearment," and "As Good as It Gets": 2 wds. |
| 50% | CHARLIZETHERON | 14 | 15-Across and 29-Across star who won a Best Actress Oscar for "Monster" and who turns 45 today (2 wds.) |
| 50% | HELENHAYES | 10 | Actress who won the Emmy, Grammy, Oscar, and Tony (one of her two Oscars was for "Airport"): 2 wds. |
| 50% | SHAWNJOHNSON | 12 | Gymnast who won season 8 and was runner-up in season 15 of "Dancing With the Stars": 2 wds. |
| 50% | MIRACLEWORKER | 13 | With "The," 1962 film for which 15-Across won an Oscar for portraying Helen Keller: 2 wds. |
| 50% | SAMSMITH | 8 | Nonbinary singer who won an Oscar for the Bond theme "Writing's on the Wall": 2 wds. |
| 50% | CHRISTIANBALE | 13 | "American Hustle" actor who won an Oscar for his role in 48-Across' "The Fighter": 2 wds. |
| 50% | ALLISONJANNEY | 13 | Actress who won an Oscar for "I, Tonya" and an Emmy for "Mom": 2 wds. |
| 50% | 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. |
| 50% | NICOLEKIDMAN | 12 | Actress who won an Oscar for Best Actress for "The Hours" and a Worst Screen Couple Razzie Award with Will Ferrell for "Bewitched": 2 wds. |
| 50% | LUPITANYONGO | 12 | "12 Years a Slave," 18-Across, and 32-Across star who was the first Kenyan-Mexican actress to win an Oscar (2 wds.) |
| 49% | WILLIAMHURT | 11 | "Kiss of the Spider Woman" Oscar winner and star of 15-Across and 43-Across who turns 70 tomorrow (2 wds.) |
| 49% | PETERJACKSON | 12 | Filmmaker who won three Oscars (Best Picture, Director, and Adapted Screenplay) for 2003's "The Lord of the Rings: The Return of the King": 2 wds. |