| 100% | LINE | 4 | "A Chorus ___," Broadway musical that won the Pulitzer Prize for Drama in 1976 |
| 73% | PARK | 4 | "Sunday in the ___ with George," Broadway musical that won the Pulitzer Prize for Drama in 1985 |
| 70% | HOW | 3 | "___ to Succeed in Business Without Really Trying," Broadway musical that won the Pulitzer Prize for Drama in 1962 |
| 65% | FIORELLO | 8 | 1959 Broadway musical that won a Pulitzer Prize for drama |
| 56% | SING | 4 | "Of Thee I ___," Broadway musical that was the first musical to win the Pulitzer Prize for Drama |
| 55% | MILLER | 6 | Arthur ___, 20th-century playwright who won the Pulitzer Prize for Drama in 1949 |
| 55% | SAMSHEPARD | 10 | Playwright whose "Buried Child" won the Pulitzer Prize for Drama in 1979: 2 wds. |
| 55% | DAVIDMAMET | 10 | Playwright whose "Glengarry Glen Ross" won the Pulitzer Prize for Drama in 1984: 2 wds. |
| 52% | RENT | 4 | One of 10 musicals to win the Pulitzer Prize for Drama |
| 52% | RENT | 4 | Seventh of 10 musicals to win the Pulitzer Prize for Drama |
| 50% | AUGUSTWILSON | 12 | Playwright whose "Fences" and "The Piano Lesson" won the Pulitzer Prize for Drama in 1987 and 1990: 2 wds. |
| 49% | THEWILDIRIS | 11 | Collection by 36-Across that won the Pulitzer Prize for Poetry in 1993 (3 wds.) |
| 48% | DAMN | 4 | Kendrick Lamar album that won the Pulitzer Prize for Music |
| 48% | DAMN | 4 | 2017 Kendrick Lamar album that won the Pulitzer Prize for Music |
| 47% | HARVEY | 6 | 1944 Broadway play by Mary Chase that won the 1945 Pulitzer Prize for Drama |
| 47% | LESS | 4 | 2018 novel by Andrew Sean Greer that won the Pulitzer Prize for Fiction |
| 47% | THEOVERSTORY | 12 | Novel by 30-Across that won the Pulitzer Prize for Fiction (2 wds.) |
| 46% | THEOVERSTORY | 12 | 2018 novel by 32-Across that won the Pulitzer Prize for Fiction (2 wds.) |
| 46% | IRAGERSHWIN | 11 | Lyricist whose 1931 Broadway musical Of Thee I Sing won a Pulitzer Prize for Drama |
| 46% | CRUZ | 4 | Nilo —, author of 2003 Pulitzer Prize for drama-winning stage play Anna in the Tropics |
| 45% | THEKINGANDI | 11 | Broadway musical that starred 45-Across as Anna Leonowens for one month in 1978 (earning her a Drama Desk Award nomination) (4 wds.) |
| 45% | LESS | 4 | Novel by Andrew Sean Greer that won the Pulitzer Prize in 2018 |
| 43% | IRA | 3 | Songwriter Gershwin who won a Pulitzer Prize for the 1932 musical "Of Thee I Sing" |
| 43% | COLOR | 5 | "The ___ Purple," Alice Walker's 1982 epistolary novel that won the Pulitzer Prize for Fiction |
| 42% | DONNATARTT | 10 | Mississippi novelist who won the Pulitzer Prize for Fiction in 2014 (2 wds.) |
| 42% | OLIO | 4 | Tyehimba Jess' book that won the 2017 Pulitzer Prize for Poetry |
| 42% | COPPERHEAD | 10 | "Demon ___," Barbara Kingsolver novel that won the 2023 Pulitzer Prize for Fiction |
| 42% | STUDIOCITY | 10 | Series about a fictional soap opera that won the Daytime Emmy Award for Outstanding Limited Drama Series in 2021 (2 wds.) |
| 42% | THEREIVERS | 10 | "___: A Reminiscence," the last novel by William Faulkner that won the Pulitzer Prize for Fiction: 2 wds. |