| 100% | AUGUSTWILSON | 12 | Playwright whose "Fences" and "The Piano Lesson" won the Pulitzer Prize for Drama in 1987 and 1990: 2 wds. |
| 59% | SAMSHEPARD | 10 | Playwright whose "Buried Child" won the Pulitzer Prize for Drama in 1979: 2 wds. |
| 59% | DAVIDMAMET | 10 | Playwright whose "Glengarry Glen Ross" won the Pulitzer Prize for Drama in 1984: 2 wds. |
| 52% | RICHARDPOWERS | 13 | American novelist whose novel "The Overstory" won the Pulitzer Prize for Fiction in 2019: 2 wds. |
| 51% | WILSON | 6 | August —, Pulitzer Prize for Drama winner for The Piano Lesson and Fences |
| 50% | THORNTONWILDER | 14 | "Our Town" playwright who won Pulitzer Prizes for both Drama and Fiction: 2 wds. |
| 49% | MILLER | 6 | Arthur ___, 20th-century playwright who won the Pulitzer Prize for Drama in 1949 |
| 48% | ANNAQUINDLEN | 12 | "One True Thing," 14-Across, and 26-Across/29-Across novelist who won the Pulitzer Prize for Commentary in 1992 (2 wds.) |
| 46% | SYLVIAPLATH | 11 | American poet and novelist who won a posthumous Pulitzer Prize for "The Collected Poems" in 1982: 2 wds. |
| 45% | ROBERTFROST | 11 | American poet behind "A Witness Tree" who won the Pulitzer Prize in 1924, 1931, 1937 and 1943: 2 wds. |
| 45% | DONNATARTT | 10 | Mississippi novelist who won the Pulitzer Prize for Fiction in 2014 (2 wds.) |
| 45% | PULITZERPRIZE | 13 | Award that 14-Across won twice, for "Fences" and "The Piano Lesson": 2 wds. |
| 44% | LINE | 4 | "A Chorus ___," Broadway musical that won the Pulitzer Prize for Drama in 1976 |
| 44% | RICHARDWILBUR | 13 | American poet behind "Things of This World" who won the Pulitzer Prize in 1957 and 1989: 2 wds. |
| 43% | LARRYMCMURTRY | 13 | American novelist whose 1985 novel "Lonesome Dove" won the Pulitzer Prize and whose six novels were adapted into films: 2 wds. |
| 43% | AUGUSTWILSON | 12 | Playwright of the month who wrote "Fences" and "The Piano Lesson": 2 wds. |
| 43% | PARK | 4 | "Sunday in the ___ with George," Broadway musical that won the Pulitzer Prize for Drama in 1985 |
| 43% | EDDIEMURPHY | 11 | "The Nutty Professor" actor and "SNL" star who won the Mark Twain Prize for American Humor in 2015: 2 wds. |
| 42% | COLSON | 6 | Whitehead whose novel “The Nickel Boys” won the Pulitzer Prize for fiction in May, 2020 |
| 42% | HOW | 3 | "___ to Succeed in Business Without Really Trying," Broadway musical that won the Pulitzer Prize for Drama in 1962 |
| 42% | SAMSHEPARD | 10 | Writer, actor, and director who won a Pulitzer Prize for the play "Buried Child" (2 wds.) |
| 42% | EDITHWHARTON | 12 | 13-Across and 25-Across writer who was the first woman to win a Pulitzer Prize in Literature, for her 1920 novel "The Age of Innocence" (2 wds.) |
| 42% | THEWILDIRIS | 11 | Collection by 36-Across that won the Pulitzer Prize for Poetry in 1993 (3 wds.) |
| 42% | WILLFERRELL | 11 | "Elf" actor and "Saturday Night Live" star who won the Mark Twain Prize for American Humor in 2011: 2 wds. |
| 41% | NORMANMAILER | 12 | "The Executioner's Song" novelist who won Pulitzer Prizes for both Fiction and General Nonfiction: 2 wds. |
| 41% | MICHAELJORDAN | 13 | Former Chicago Bulls player who won the NBA Slam Dunk Contest in 1987 and 1988: 2 wds. |
| 40% | BERNARDSHAW | 11 | Irish playwright George ___ whose volume of work including "Man and Superman" won him a Nobel Prize in Literature: 2 wds. |
| 40% | ROBERTFROST | 11 | 17-Across and 26-Across writer who is the only person to win four Pulitzer Prizes for Poetry (2 wds.) |
| 40% | BENKINGSLEY | 11 | Actor whose birthday it is today who won an Academy Award for playing Gandhi in the titular film and was knighted in 2002: 2 wds. |
| 40% | THEREIVERS | 10 | "___: A Reminiscence," the last novel by William Faulkner that won the Pulitzer Prize for Fiction: 2 wds. |