| 100% | SAMUELBARBER | 12 | "Adagio for Strings" artist who won Pulitzer Prize for Music twice and is widely known for "Knoxville: Summer of 1915": 2 wds. |
| 66% | ELLIOTTCARTER | 13 | "Holiday Overture" artist who won Pulitzer Prize twice and is widely known for "String Quartet No. 2 and 3": 2 wds. |
| 62% | WALTERPISTON | 12 | "Viola Concerto" (1957) artist who won Pulitzer Prize twice and is widely known for "Symphony No. 3 and 7": 2 wds. |
| 42% | CARLSANDBURG | 12 | "Fog" poet who won Pulitzer Prizes for both Poetry and History: 2 wds. |
| 42% | THORNTONWILDER | 14 | "Our Town" playwright who won Pulitzer Prizes for both Drama and Fiction: 2 wds. |
| 41% | 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.) |
| 41% | NORMANMAILER | 12 | "The Executioner's Song" novelist who won Pulitzer Prizes for both Fiction and General Nonfiction: 2 wds. |
| 39% | ROBERTFROST | 11 | 17-Across and 26-Across writer who is the only person to win four Pulitzer Prizes for Poetry (2 wds.) |
| 37% | CARDIB | 6 | "Up" rapper who won the American Music Award for Favorite Rap/Hip-Hop Artist twice: 2 wds. |
| 37% | RICHARDWILBUR | 13 | American poet behind "Things of This World" who won the Pulitzer Prize in 1957 and 1989: 2 wds. |
| 37% | MARTINSCORSESE | 14 | New Hollywood director who won an Oscar for "The Departed," and is the most-nominated director alive in terms of Oscars: 2 wds. |
| 37% | HELENHAYES | 10 | Actress who won the Emmy, Grammy, Oscar, and Tony (one of her two Oscars was for "Airport"): 2 wds. |
| 36% | BRENTMUSBURGER | 14 | Sports commentator who was one the members of "The NFL Today" and is known for coining the phrase "March Madness": 2 wds. |
| 36% | LAURYNHILL | 10 | "Everything Is Everything" singer who received the Grammys for both Album of the Year and Best New Artist in 1999: 2 wds. |
| 36% | SYLVIAPLATH | 11 | American poet and novelist who won a posthumous Pulitzer Prize for "The Collected Poems" in 1982: 2 wds. |
| 36% | HARRYSTYLES | 11 | "As It Was" singer who won the People's Choice Award for Male Artist of 2022: 2 wds. |
| 36% | BAZLUHRMANN | 11 | Australian director of 19- and 33-Across who's known for films with pop music soundtracks: 2 wds. |
| 36% | CHUCKBERRY | 10 | American songwriter who was one of the pioneers of Rock and Roll and was known for his song "Johnny B. Goode": 2 wds. |
| 35% | DIANAROSS | 9 | American singer who was the lead singer of "The Supremes" and is known for her solo songs like "Upside Down": 2 wds. |
| 35% | SOPHIECRUZ | 10 | Young American activist who is known for ensuring continuance of the DAPA program and was featured in the short "Free Like the Birds": 2 wds. |
| 35% | NORAHJONES | 10 | "Don't Know Why" singer who won the Best New Artist and Record of the Year Grammys in 2003: 2 wds. |
| 34% | ROBINWRIGHT | 11 | American actress whose birthday it is today and who is known for playing Claire Underwood in Netflix series "House of Cards": 2 wds. |
| 34% | GRETATHUNBERG | 13 | Young Swedish environmental activist who is known for urging action on global warming and was nominated for the 2019 Nobel Peace Prize: 2 wds. |
| 34% | KEITHJACKSON | 12 | Sports commentator known for his distinctive voice and career with ABC Sports who is best known for his coverage of college football: 2 wds. |
| 34% | LUKECOMBS | 9 | 15-Across and 33-Across singer who won the 2019 Country Music Association's New Artist of the Year Award (2 wds.) |
| 34% | STEPHENSTILLS | 13 | American singer and songwriter who is the first artist to be inducted twice on the same night into the Rock and Roll Hall of Fame: 2 wds. |
| 34% | SAMSHEPARD | 10 | Writer, actor, and director who won a Pulitzer Prize for the play "Buried Child" (2 wds.) |
| 33% | EDSHEERAN | 9 | "Shape Of You" artist who won the award for the Top Male Artist in Billboard 2018: 2 wds. |
| 33% | JOHNLENNON | 10 | English songwriter who co-founded the Beatles and is known for his song "Imagine": 2 wds. |
| 33% | POSTMALONE | 10 | 18-Across, 27-Across, and 34-Across rapper/singer who won the 2025 American Music Award for Favorite Country Male Artist (2 wds.) |