| 100% | GMAN | 4 | Book about J. Edgar Hoover that won the 2023 Pulitzer Prize for Biography |
| 53% | COPPERHEAD | 10 | "Demon ___," Barbara Kingsolver novel that won the 2023 Pulitzer Prize for Fiction |
| 52% | GMAN | 4 | 2023 Pulitzer Prize-winning biography of J. Edgar Hoover |
| 47% | OLIO | 4 | Tyehimba Jess' book that won the 2017 Pulitzer Prize for Poetry |
| 41% | THESIEGEOF | 10 | & 10D J G Farrell novel that won the 1973 Booker Prize for Fiction |
| 41% | DAMN | 4 | Kendrick Lamar album that won the Pulitzer Prize for Music |
| 40% | DAMN | 4 | 2017 Kendrick Lamar album that won the Pulitzer Prize for Music |
| 40% | LESS | 4 | 2018 novel by Andrew Sean Greer that won the Pulitzer Prize for Fiction |
| 40% | THEOVERSTORY | 12 | Novel by 30-Across that won the Pulitzer Prize for Fiction (2 wds.) |
| 40% | LINE | 4 | "A Chorus ___," Broadway musical that won the Pulitzer Prize for Drama in 1976 |
| 39% | THEOVERSTORY | 12 | 2018 novel by 32-Across that won the Pulitzer Prize for Fiction (2 wds.) |
| 39% | THEWILDIRIS | 11 | Collection by 36-Across that won the Pulitzer Prize for Poetry in 1993 (3 wds.) |
| 38% | THESHIPPING | 11 | & 22D E Annie Proulx novel that won the 1994 Pulitzer Prize for Fiction |
| 38% | HOW | 3 | "___ to Succeed in Business Without Really Trying," Broadway musical that won the Pulitzer Prize for Drama in 1962 |
| 38% | HARVEY | 6 | 1944 Broadway play by Mary Chase that won the 1945 Pulitzer Prize for Drama |
| 37% | OVERSTORY | 9 | "The ___," novel by Richard Powers that won the 2019 Pulitzer Prize for Fiction |
| 37% | RAILROAD | 8 | "The Underground ___," Colson Whitehead novel that won the 2017 Pulitzer Prize for Fiction |
| 37% | NIGHT | 5 | "The ___ Watchman," Louise Erdrich novel that won the 2021 Pulitzer Prize for Fiction |
| 37% | BOYS | 4 | "The Nickel ___," Colson Whitehead novel that won the 2020 Pulitzer Prize for Fiction |
| 36% | RENT | 4 | Miusical that won the 1996 Pulitzer Prize |
| 36% | MACLEISH | 8 | His "J.B." won the 1959 Pulitzer Prize for Drama |
| 36% | COLSONWHITEHEAD | 15 | He won the 2017 Pulitzer Prize for fiction |
| 36% | COLOR | 5 | "The ___ Purple," Alice Walker's 1982 epistolary novel that won the Pulitzer Prize for Fiction |
| 35% | WOMEN | 5 | "___ Talking," drama film that won the 2023 Oscar for Best Adapted Screenplay |
| 35% | NIGHT | 5 | "The ___ Watchman," 2020 novel by Louise Erdrich that won the 2021 Pulitzer Prize for Fiction |
| 35% | TARTT | 5 | Author who won the 2014 Pulitzer Prize for Fiction |
| 35% | SHAW | 4 | Caroline who won the 2013 Pulitzer Prize for Music |
| 34% | LONESOMEDOVE | 12 | Western novel that won the 1986 Pulitzer Prize: 2 wds. |