| 100% | CARLSANDBURG | 12 | "Fog" poet who won Pulitzer Prizes for both Poetry and History: 2 wds. |
| 64% | THORNTONWILDER | 14 | "Our Town" playwright who won Pulitzer Prizes for both Drama and Fiction: 2 wds. |
| 60% | NORMANMAILER | 12 | "The Executioner's Song" novelist who won Pulitzer Prizes for both Fiction and General Nonfiction: 2 wds. |
| 53% | ELLIOTTCARTER | 13 | "Holiday Overture" artist who won Pulitzer Prize twice and is widely known for "String Quartet No. 2 and 3": 2 wds. |
| 53% | WALTERPISTON | 12 | "Viola Concerto" (1957) artist who won Pulitzer Prize twice and is widely known for "Symphony No. 3 and 7": 2 wds. |
| 51% | SYLVIAPLATH | 11 | American poet and novelist who won a posthumous Pulitzer Prize for "The Collected Poems" in 1982: 2 wds. |
| 49% | SAMUELBARBER | 12 | "Adagio for Strings" artist who won Pulitzer Prize for Music twice and is widely known for "Knoxville: Summer of 1915": 2 wds. |
| 45% | MARGARETATWOOD | 14 | Author who won the Booker Prize for "The Blind Assassin" and "The Testaments": 2 wds. |
| 42% | MARYOLIVER | 10 | Pulitzer Prize-winning poet whose poems include "The Summer Day" and "Wild Geese": 2 wds. |
| 42% | SAMSHEPARD | 10 | Writer, actor, and director who won a Pulitzer Prize for the play "Buried Child" (2 wds.) |
| 41% | RICHARDWILBUR | 13 | American poet behind "Things of This World" who won the Pulitzer Prize in 1957 and 1989: 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% | ROBERTFROST | 11 | American poet behind "A Witness Tree" who won the Pulitzer Prize in 1924, 1931, 1937 and 1943: 2 wds. |
| 40% | DONNATARTT | 10 | Mississippi novelist who won the Pulitzer Prize for Fiction in 2014 (2 wds.) |
| 40% | MERYLSTREEP | 11 | Actress who won a Golden Globe and an Oscar for both "Sophie's Choice" and "The Iron Lady" (2 wds.) |
| 39% | JODIEFOSTER | 11 | Actress who won a Golden Globe and an Oscar for both "The Accused" and "The Silence of the Lambs" (2 wds.) |
| 39% | SALMANRUSHDIE | 13 | Author who won the Booker Prize for "Midnight's Children": 2 wds. |
| 39% | INGRIDBERGMAN | 13 | Actress who won a Golden Globe and an Oscar for both "Gaslight" and "Anastasia" (2 wds.) |
| 38% | MAGICJOHNSON | 12 | Hall of Fame Lakers legend who won both NCAA and NBA championships: 2 wds. |
| 38% | MICHAELJORDAN | 13 | Hall of Fame Bulls legend who won both NCAA and NBA championships: 2 wds. |
| 38% | JOHNHAVLICEK | 12 | Hall of Fame Celtics legend who won both NCAA and NBA championships: 2 wds. |
| 38% | JORDANSPIETH | 12 | Golfer who won both the Masters and the US Open in 2015: 2 wds. |
| 38% | JACKNICKLAUS | 12 | Golfer who won both the Masters and the US Open in 1972: 2 wds. |
| 38% | KAZUOISHIGURO | 13 | Author who won the Booker Prize for "The Remains of the Day": 2 wds. |
| 38% | SALMANRUSHDIE | 13 | Author who won the Man Booker Prize in 1981 for "Midnight's Children": 2 wds. |
| 38% | ALLISONJANNEY | 13 | Actress who won two Emmys in 2014, for "Mom" and "Masters of Sex": 2 wds. |
| 38% | LEETREVINO | 10 | Golfer nicknamed "Supermex" who won both the US Open and the US Senior Open: 2 wds. |
| 38% | DONNEWCOMBE | 11 | Dodgers pitcher who won both the Cy Young Award and MVP honors in 1956: 2 wds. |
| 38% | CLAYTONKERSHAW | 14 | Dodgers pitcher who won both the Cy Young Award and MVP honors in 2014: 2 wds. |
| 38% | SANDYKOUFAX | 11 | Dodgers pitcher who won both the Cy Young Award and MVP honors in 1963: 2 wds. |