| 100% | LEONARDS | 8 | Pitts who won the 2004 Pulitzer for Commentary and Roberts who costarred in "Drumline: A New Beat" |
| 43% | ANNAQUINDLEN | 12 | "One True Thing," 14-Across, and 26-Across/29-Across novelist who won the Pulitzer Prize for Commentary in 1992 (2 wds.) |
| 40% | ZAYN | 4 | "Pillowtalk" singer who won the Billboard Music Award for New Artist of the Year as a member of One Direction in 2013 and as a solo artist in 2017 |
| 40% | MARK | 4 | ___ Ingram II, former NFL running back born in December who won a Heisman Trophy and played for the New Orleans Saints |
| 38% | BRAD | 4 | ___ Pitt, "Once Upon a Time in Hollywood" actor who won the SAG award for Best Supporting Actor in 2020 |
| 38% | SYLVIAPLATH | 11 | American poet and novelist who won a posthumous Pulitzer Prize for "The Collected Poems" in 1982: 2 wds. |
| 38% | EDITHWHARTON | 12 | 13-Across and 25-Across writer who was the first woman to win a Pulitzer Prize in Literature, for her 1920 novel "The Age of Innocence" (2 wds.) |
| 37% | EANNIEPROULX | 12 | 17-Across and 38-Across novelist who won the 1994 Pulitzer Prize for Fiction for "The Shipping News" (3 wds.) |
| 37% | OLEN | 4 | "A Good Scent from a Strange Mountain" author Robert ___ Butler who won the Pulitzer Prize in 1993 |
| 36% | CATEBLANCHETT | 13 | Actress who won a Best Supporting Actress Oscar for playing Katharine Hepburn in the 2004 film "The Aviator" (2 wds.) |
| 36% | SAMSHEPARD | 10 | Writer, actor, and director who won a Pulitzer Prize for the play "Buried Child" (2 wds.) |
| 36% | HALLEBERRY | 10 | "Monster's Ball" Oscar winner who won a Razzie Award for her starring role in the 2004 film "Catwoman" (2 wds.) |
| 35% | ALLISONJANNEY | 13 | Actress who won the 2004 Emmy Award for Outstanding Lead Actress in a Drama Series for playing C.J. Cregg on "The West Wing" (2 wds.) |
| 35% | BRYANCRANSTON | 13 | "Breaking Bad" actor who won two Tony Awards for Best Actor in a Play, for "All the Way" and "Network" (2 wds.) |
| 35% | JODIEFOSTER | 11 | Actress who won a Golden Globe for "The Silence of the Lambs" and won their Cecil B. DeMille Award in 2013: 2 wds. |
| 35% | 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. |
| 34% | GWENJORGENSEN | 13 | American distance runner and two-time ITU World Champion who was the first to win a triathlon gold for USA in the Olympics: 2 wds. |
| 34% | FROST | 5 | American writer Robert, who won four Pulitzers and the Congressional Gold Medal, and is best known for "The Road Not Taken" |
| 34% | SAMMENDES | 9 | "The Ferryman" director who won the Tony Award for Best Direction of a Play in 2019 (2 wds.) |
| 34% | BRAD | 4 | ___ Pitt, actor who won an award for the Best Supporting Actor for "Once Upon a Time in Hollywood" at the 92nd Academy Awards |
| 34% | DONNATARTT | 10 | Mississippi novelist who won the Pulitzer Prize for Fiction in 2014 (2 wds.) |
| 34% | MILLER | 6 | Arthur ___, 20th-century playwright who won the Pulitzer Prize for Drama in 1949 |
| 34% | GERALDMCRANEY | 13 | Actor who won the 2017 Emmy for Outstanding Guest Actor in a Drama Series for playing the obstetrician who delivered Kevin and Kate in NBC's "This Is Us" (2 wds.) |
| 34% | NEIL | 4 | With 15-Across, "How I Met Your Mother" actor who won a 2014 Tony Award for starring in "Hedwig and the Angry Inch" |
| 34% | RESTON | 6 | James, journalist who won the Pulitzer in 1945 and 1957 |
| 34% | ROBERTFROST | 11 | American poet behind "A Witness Tree" who won the Pulitzer Prize in 1924, 1931, 1937 and 1943: 2 wds. |
| 34% | YULBRYNNER | 10 | Actor who won a Tony and an Oscar for playing King Mongkut in "The King and I": 2 wds. |
| 34% | LEDGER | 6 | Heath ___ who won his only Oscar for playing "The Joker" and has a wax statue in Madame Tussauds, Sydney |
| 33% | RODDYRICCH | 10 | "The Box" rapper who won the BET Award for Best New Artist in 2020: 2 wds. |
| 33% | EMINEM | 6 | Rapper who won the Grammy Award for Best Rap Song in 2004 for "Lose Yourself" |