| 100% | HOLIDAY | 7 | Billie ___, multiple Grammy-winning singer-songwriter nicknamed "Lady Day" |
| 53% | HOLIDAY | 7 | Billie —, US jazz singer whose nickname was Lady Day |
| 47% | KING | 4 | Carole ___, multiple Grammy-winning singer-songwriter and the first female recipient of the Library of Gershwin Prize |
| 47% | CHER | 4 | A grammy winning singer nicknamed the "Goddess of Pop," who sang the hit song "Believe" |
| 47% | EILISH | 6 | Grammy-winning singer billie |
| 46% | TAYLORSWIFT | 11 | Multiple Grammy-winning singer-songwriter who is the first-ever recipient of Billboard's Woman of the Decade Award: 2 wds. |
| 45% | JONI | 4 | ___ Mitchell, multiple Grammy-winning singer-songwriter and the first female musician to become a Companion of the Order of Canada |
| 44% | ENYA | 4 | Grammy-winning “Book of Days” singer |
| 44% | NICKS | 5 | Stevie ___, multiple Grammy-winning singer-songwriter and the only woman to be inducted twice into the Rock and Roll Hall of Fame |
| 43% | ADELE | 5 | Grammy winning singer of "Hello" |
| 43% | EILISH | 6 | Billie ___, singer who won five Grammy awards including Record of the Year in 2020 |
| 42% | SARA | 4 | Grammy-winning singer-songwriter Bareilles |
| 41% | WEIRDAL | 7 | Grammy winning parody singer |
| 40% | TEENA | 5 | Singer Marie nicknamed Lady T |
| 39% | ADELE | 5 | British singer-songwriter who won six prizes at the 2012 Grammy Awards |
| 39% | ADELE | 5 | English singer-songwriter who won Grammy Awards for "25" and 14-Across |
| 38% | RAITT | 5 | 10-time Grammy-winning singer/songwriter/guitarist Bonnie |
| 38% | CARLY | 5 | Singer/songwriter Simon who won a Grammy and an Oscar for "Let the River Run" |
| 38% | HELENHAYES | 10 | American actress nicknamed "First Lady of American Theatre" who has won the EGOT (Emmy, Grammy, Oscar, and Tony): 2 wds. |
| 38% | PEABO | 5 | Grammy Award-winning singer-songwriter Bryson |
| 38% | TAYLORSWIFT | 11 | Singer-songwriter whose "1989" won 2016's Grammy Award for Album of the Year (2 wds.) |
| 37% | LADYDAY | 7 | Singer Billie Holiday's nickname |
| 37% | JASONISBELL | 11 | Grammy-winning singer-songwriter on 11-Across and 24-Across (2 wds.) |
| 37% | RAVISHANKAR | 11 | Sitar maestro who collaborated with "The Beatles" and who is the father of multiple Grammy-winning singer Norah Jones: 2 wds. |
| 37% | LADY | 4 | ___ Day, nickname for Billie Holiday |
| 36% | PEABOBRYSON | 11 | Singer/songwriter who won Grammy Awards for 34-Across and the "Beauty and the Beast" theme (2 wds.) |
| 35% | BESTRAPPERFORMANCE | 18 | Grammy category won multiple times by Kendrick Lamar |
| 35% | MARS | 4 | Singer Bruno who won six 2017 Grammy Awards |
| 35% | ART | 3 | Singer ___ Garfunkel who has won eight Grammy Awards |
| 35% | ANNIE | 5 | Grammy-winning singer Lennox |