| 100% | EDSHEERAN | 9 | "Shape of You" singer/songwriter who co-wrote and sings 36-Across with 28-Across (2 wds.) |
| 74% | JUSTINBIEBER | 12 | "Peaches" singer/songwriter who co-wrote and sings 36-Across with 17-Across (2 wds.) |
| 51% | KENNYROGERS | 11 | Country Music Hall of Fame singer who collaborated with 17-Across and 28-Across (2 wds.) |
| 50% | LINDARONSTADT | 13 | Rock and Roll Hall of Fame singer who collaborated with 15-Across and 28-Across on "Trio" (2 wds.) |
| 50% | DONNYHATHAWAY | 13 | Singer of 15-Across who also sang duets with Roberta Flack: 2 wds. |
| 48% | EMMYLOUHARRIS | 13 | Country Music Hall of Fame singer who collaborated with 28-Across and 43-Across on the Grammy-winning 1987 album "Trio" (2 wds.) |
| 48% | THOMASRHETT | 11 | Singer/songwriter who collaborated with 17-Across, 28-Across, Reba McEntire, and Keith Urban on the country hit "Be a Light" (2 wds.) |
| 48% | RINGOSTARR | 10 | 19-Across drummer who also wrote and sang 31-Across: 2 wds. |
| 47% | SARABAREILLES | 13 | Singer/songwriter who wrote music and lyrics for the stage adaptation of "Waitress" (2 wds.) |
| 47% | DOLLYPARTON | 11 | Country Music Hall of Fame singer who covers "Every Breath You Take" with Sting and "Open Arms" with Steve Perry on 48-Across (2 wds.) |
| 47% | CURTISMAYFIELD | 14 | Group member who wrote and sang 48-Across: 2 wds. |
| 46% | DEMILOVATO | 10 | "Tell Me You Love Me" singer who sings 25-Across with Christina Aguilera (2 wds.) |
| 44% | JOHNLEGEND | 10 | "All of Me" singer who sang backup for Alicia Keys and Kanye West: 2 wds. |
| 44% | DOLLYPARTON | 11 | Country Music Hall of Fame singer who collaborated with 15-Across and 43-Across on "Trio" (2 wds.) |
| 44% | LEONARDCOHEN | 12 | "Hallelujah" singer-songwriter who wrote "Book of Longing," a book of poetry and drawings (2 wds.) |
| 44% | PATTISMITH | 10 | "Because the Night" singer-songwriter who wrote "Babel," a book of poetry and drawings (2 wds.) |
| 43% | SARABAREILLES | 13 | "Love Song" singer-songwriter who recorded the duets "Love Won't Let You Get Away" and "Baby, It's Cold Outside" with 32-Across (2 wds.) |
| 43% | LEONARDCOHEN | 12 | Canadian singer/songwriter who wrote and recorded 34-Across in 1984 (2 wds.) |
| 43% | MARYSHELLEY | 11 | Author who began writing 28-Across at the age of 18: 2 wds. |
| 43% | BILLYPRESTON | 12 | Singer who sang with Nat King Cole on a TV show at 11 and released his first album at 16: 2 wds. |
| 43% | SHELLEYFABARES | 14 | Actress and singer who's the niece of 19-Across: 2 wds. |
| 43% | DEBBIEGIBSON | 12 | "Electric Youth" singer who sings "Heartbreak Holiday" with 18-Across and "White Christmas" with her father on 30-Across (2 wds.) |
| 42% | JAMESTAYLOR | 11 | Singer/songwriter who appeared on the March 1, 1971, cover of Time Magazine with the headline "The New Rock: Bittersweet and Low" (2 wds.) |
| 42% | JONIMITCHELL | 12 | "Both Sides Now" singer-songwriter who wrote "Morning Glory on the Vine," a book of poetry and drawings (2 wds.) |
| 42% | MARYTRAVERS | 11 | Folk singer who, in a trio with Peter and Paul, sang the 1963 hit "Puff, the Magic Dragon": 2 wds. |
| 42% | NORAHJONES | 10 | "Come Away With Me" singer who received the Grammys for both Album of the Year and Best New Artist in 2003: 2 wds. |
| 42% | RAVISHANKAR | 11 | Sitar maestro who collaborated with "The Beatles" and who is the father of multiple Grammy-winning singer Norah Jones: 2 wds. |
| 42% | EDSHEERAN | 9 | English singer whose album "÷" and song "Shape of You" both topped the charts in 2017: 2 wds. |
| 42% | DAMIANMCGINTY | 13 | Irish singer who played Rory Flanagan on "Glee" and was a member of 32-Across: 2 wds. |
| 42% | DONDELILLO | 10 | Author of "Libra" and "Mao II" who wrote 18-, 26-, and 35-Across: 2 wds. |