| 100% | THEOVERSTORY | 12 | Richard Powers novel that won the 2019 Pulitzer Prize (2 wds.) |
| 70% | LONESOMEDOVE | 12 | Western novel that won the 1986 Pulitzer Prize: 2 wds. |
| 69% | OVERSTORY | 9 | "The ___," novel by Richard Powers that won the 2019 Pulitzer Prize for Fiction |
| 66% | THEGOLDFINCH | 12 | Donna Tartt novel that won the 2014 Pulitzer Prize (2 wds.) |
| 60% | THENICKELBOYS | 13 | Colson Whitehead novel that won the 2020 Pulitzer Prize (3 wds.) |
| 54% | THEOVERSTORY | 12 | Novel by 30-Across that won the Pulitzer Prize for Fiction (2 wds.) |
| 54% | THENICKELBOYS | 13 | 2019 Colson Whitehead novel, about the Dozier School, that won the Pulitzer Prize: 3 wds. |
| 53% | RICHARDPOWERS | 13 | American novelist whose novel "The Overstory" won the Pulitzer Prize for Fiction in 2019: 2 wds. |
| 52% | THEOVERSTORY | 12 | 2018 novel by 32-Across that won the Pulitzer Prize for Fiction (2 wds.) |
| 51% | OURS | 4 | "One of ___" (Willa Cather novel that won the Pulitzer Prize) |
| 50% | LESS | 4 | Andrew Sean Greer novel that won the 2018 Pulitzer Prize |
| 50% | GAIN | 4 | Novel by Richard Powers that won the James Fenimore Cooper Prize for Best Historical Fiction in 1999 |
| 49% | THEREIVERS | 10 | "___: A Reminiscence," the last novel by William Faulkner that won the Pulitzer Prize for Fiction: 2 wds. |
| 49% | SPACECOWBOY | 11 | Kacey Musgraves single that won the 2019 Grammy for Best Country Song: 2 wds. |
| 47% | THESHIPPING | 11 | & 22D E Annie Proulx novel that won the 1994 Pulitzer Prize for Fiction |
| 47% | THEWILDIRIS | 11 | Collection by 36-Across that won the Pulitzer Prize for Poetry in 1993 (3 wds.) |
| 47% | COPPERHEAD | 10 | "Demon ___," Barbara Kingsolver novel that won the 2023 Pulitzer Prize for Fiction |
| 46% | GREENBOOK | 9 | American comedy-drama film that won the 2019 Golden Globe Award for Best Motion Picture - Musical or Comedy: 2 wds. |
| 46% | BARTONFINK | 10 | John Turturro movie that won the top prize at the Cannes Film Festival in 1991: 2 wds. |
| 46% | RAILROAD | 8 | "The Underground ___," Colson Whitehead novel that won the 2017 Pulitzer Prize for Fiction |
| 46% | NIGHT | 5 | "The ___ Watchman," Louise Erdrich novel that won the 2021 Pulitzer Prize for Fiction |
| 46% | BOYS | 4 | "The Nickel ___," Colson Whitehead novel that won the 2020 Pulitzer Prize for Fiction |
| 45% | TAXIDRIVER | 10 | Robert De Niro movie that won the top prize at the Cannes Film Festival in 1976: 2 wds. |
| 45% | COLOR | 5 | "The ___ Purple," Alice Walker's 1982 epistolary novel that won the Pulitzer Prize for Fiction |
| 45% | SAMSHEPARD | 10 | Playwright whose "Buried Child" won the Pulitzer Prize for Drama in 1979: 2 wds. |
| 45% | DAVIDMAMET | 10 | Playwright whose "Glengarry Glen Ross" won the Pulitzer Prize for Drama in 1984: 2 wds. |
| 45% | ORDINARYGRACE | 13 | William Kent Krueger novel that won the 2014 Edgar Award for Best Novel (2 wds.) |
| 45% | SPACECOWBOY | 11 | Song by 34-Across that won the 2019 Grammy for Best Country Song (2 wds.) |
| 44% | 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.) |
| 44% | SICKOMODE | 9 | Travis Scott song that won the 2019 Billboard Music Award for Top Streaming Song (Audio) (2 wds.) |