| 100% | THEWILDIRIS | 11 | Collection by 36-Across that won the Pulitzer Prize for Poetry in 1993 (3 wds.) |
| 71% | THESEVENAGES | 12 | Collection by 36-Across that was a finalist for the Pulitzer Prize for Poetry in 2002 (3 wds.) |
| 55% | THEOVERSTORY | 12 | Novel by 30-Across that won the Pulitzer Prize for Fiction (2 wds.) |
| 54% | THEOVERSTORY | 12 | 2018 novel by 32-Across that won the Pulitzer Prize for Fiction (2 wds.) |
| 46% | THEREIVERS | 10 | "___: A Reminiscence," the last novel by William Faulkner that won the Pulitzer Prize for Fiction: 2 wds. |
| 45% | DONNATARTT | 10 | Mississippi novelist who won the Pulitzer Prize for Fiction in 2014 (2 wds.) |
| 43% | LINE | 4 | "A Chorus ___," Broadway musical that won the Pulitzer Prize for Drama in 1976 |
| 43% | DAMN | 4 | Kendrick Lamar album that won the Pulitzer Prize for Music |
| 43% | SAMSHEPARD | 10 | Playwright whose "Buried Child" won the Pulitzer Prize for Drama in 1979: 2 wds. |
| 43% | LESS | 4 | 2018 novel by Andrew Sean Greer that won the Pulitzer Prize for Fiction |
| 43% | DAMN | 4 | 2017 Kendrick Lamar album that won the Pulitzer Prize for Music |
| 43% | DAVIDMAMET | 10 | Playwright whose "Glengarry Glen Ross" won the Pulitzer Prize for Drama in 1984: 2 wds. |
| 43% | LESS | 4 | Novel by Andrew Sean Greer that won the Pulitzer Prize in 2018 |
| 42% | ANDTHECITY | 10 | "Sex ___," American television show that won the Primetime Emmy Award for Outstanding Comedy Series in 2001: 3 wds. |
| 41% | THENICKELBOYS | 13 | Colson Whitehead novel that won the 2020 Pulitzer Prize (3 wds.) |
| 41% | GAIN | 4 | Novel by Richard Powers that won the James Fenimore Cooper Prize for Best Historical Fiction in 1999 |
| 41% | RICHARDPOWERS | 13 | American novelist whose novel "The Overstory" won the Pulitzer Prize for Fiction in 2019: 2 wds. |
| 41% | THEECHOMAKER | 12 | 2006 novel by 32-Across that won the National Book Award for Fiction (3 wds.) |
| 41% | JOHNFKENNEDY | 12 | Former US President who authored the Pulitzer Prize-winning book "Profiles in Courage": 3 wds. |
| 41% | CITYOFSTARS | 11 | Ryan Gosling and Emma Stone song from "La La Land" that won the Oscar for Best Original Song in 2017: 3 wds. |
| 40% | HARVEY | 6 | 1944 Broadway play by Mary Chase that won the 1945 Pulitzer Prize for Drama |
| 40% | RULEOFWOLVES | 12 | Novel by 40-Across that won the 2021 Goodreads Choice Award for Young Adult Fantasy (3 wds.) |
| 40% | PARK | 4 | "Sunday in the ___ with George," Broadway musical that won the Pulitzer Prize for Drama in 1985 |
| 40% | OVERSTORY | 9 | "The ___," novel by Richard Powers that won the 2019 Pulitzer Prize for Fiction |
| 40% | DONTWANNAFIGHT | 14 | Alabama Shakes song that won the Grammy Award for Best Rock Song in 2016: 3 wds. |
| 39% | OLIO | 4 | Tyehimba Jess' book that won the 2017 Pulitzer Prize for Poetry |
| 39% | BADGUY | 6 | 2019 song by Billie Eilish that won the Grammy Award for Record of the Year in 2020: 2 wds. |
| 39% | 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.) |
| 39% | THENICKELBOYS | 13 | 2019 Colson Whitehead novel, about the Dozier School, that won the Pulitzer Prize: 3 wds. |