| 100% | OLIO | 4 | Tyehimba Jess' book that won the 2017 Pulitzer Prize for Poetry |
| 59% | RAILROAD | 8 | "The Underground ___," Colson Whitehead novel that won the 2017 Pulitzer Prize for Fiction |
| 54% | COLSONWHITEHEAD | 15 | He won the 2017 Pulitzer Prize for fiction |
| 54% | GMAN | 4 | Book about J. Edgar Hoover that won the 2023 Pulitzer Prize for Biography |
| 51% | DAMN | 4 | 2017 Kendrick Lamar album that won the Pulitzer Prize for Music |
| 48% | INDECENCY | 9 | Book that won the 2018 National Book Award for Poetry, written by Justin Phillip Reed |
| 48% | DAMN | 4 | Kendrick Lamar album that won the Pulitzer Prize for Music |
| 47% | THEWILDIRIS | 11 | Collection by 36-Across that won the Pulitzer Prize for Poetry in 1993 (3 wds.) |
| 46% | LESS | 4 | 2018 novel by Andrew Sean Greer that won the Pulitzer Prize for Fiction |
| 46% | THEOVERSTORY | 12 | Novel by 30-Across that won the Pulitzer Prize for Fiction (2 wds.) |
| 46% | LINE | 4 | "A Chorus ___," Broadway musical that won the Pulitzer Prize for Drama in 1976 |
| 46% | THESIEGEOF | 10 | & 10D J G Farrell novel that won the 1973 Booker Prize for Fiction |
| 46% | THEOVERSTORY | 12 | 2018 novel by 32-Across that won the Pulitzer Prize for Fiction (2 wds.) |
| 45% | THESHIPPING | 11 | & 22D E Annie Proulx novel that won the 1994 Pulitzer Prize for Fiction |
| 44% | COPPERHEAD | 10 | "Demon ___," Barbara Kingsolver novel that won the 2023 Pulitzer Prize for Fiction |
| 44% | HOW | 3 | "___ to Succeed in Business Without Really Trying," Broadway musical that won the Pulitzer Prize for Drama in 1962 |
| 44% | HARVEY | 6 | 1944 Broadway play by Mary Chase that won the 1945 Pulitzer Prize for Drama |
| 44% | OVERSTORY | 9 | "The ___," novel by Richard Powers that won the 2019 Pulitzer Prize for Fiction |
| 44% | NIGHT | 5 | "The ___ Watchman," Louise Erdrich novel that won the 2021 Pulitzer Prize for Fiction |
| 44% | BOYS | 4 | "The Nickel ___," Colson Whitehead novel that won the 2020 Pulitzer Prize for Fiction |
| 43% | ROETHKE | 7 | Theodore —, writer whose volume The Waking won the 1954 Pulitzer Prize for Poetry |
| 42% | RENT | 4 | Miusical that won the 1996 Pulitzer Prize |
| 42% | COLOR | 5 | "The ___ Purple," Alice Walker's 1982 epistolary novel that won the Pulitzer Prize for Fiction |
| 41% | WALLACESTEVENS | 14 | Winner of the 1955 Pulitzer Prize for Poetry |
| 41% | ASBRAVEASYOU | 12 | 29-Across novel that won the Kirkus Prize in 2016 and the NAACP Image Award for Outstanding Literary Work for Youth/Teen in 2017 (4 wds.) |
| 41% | NIGHT | 5 | "The ___ Watchman," 2020 novel by Louise Erdrich that won the 2021 Pulitzer Prize for Fiction |
| 40% | TARTT | 5 | Author who won the 2014 Pulitzer Prize for Fiction |
| 40% | SHAW | 4 | Caroline who won the 2013 Pulitzer Prize for Music |