| 100% | SARAHVAUGHAN | 12 | Jazz singer of the 1940s and 1950s nicknamed "The Divine One": 2 wds. |
| 55% | SARAHVAUGHAN | 12 | Jazz vocalist nicknamed "The Divine One" and "Sassy": 2 wds. |
| 50% | ELLAFITZGERALD | 14 | Jazz singer nicknamed "Queen of Jazz" and "First Lady of Song": 2 wds. |
| 50% | FRANKSINATRA | 12 | Jazz crooner nicknamed "Chairman of the Board" and "Ol' Blue Eyes": 2 wds. |
| 47% | JLO | 3 | Nickname of the singer known for "All I Have" and "On the Floor": 2 wds. |
| 45% | LIZAMINNELLI | 12 | "Cabaret" star and singer who won one of the first Grammy Legend Awards, in 1990: 2 wds. |
| 43% | ARIANAGRANDE | 12 | Singer of the #1 hits "Thank U, Next" and "7 Rings": 2 wds. |
| 43% | LADYGAGA | 8 | Singer of the #1 hits "Just Dance" and "Born This Way": 2 wds. |
| 43% | SARAH | 5 | Jazz singer Vaughan nicknamed the Divine One |
| 43% | NEILYOUNG | 9 | "Heart of Gold" singer in the Rock and Roll Hall of Fame: 2 wds. |
| 43% | ZOOEYDESCHANEL | 14 | "New Girl" actress and lead singer of the band She & Him: 2 wds. |
| 42% | JLO | 3 | Nickname of actress and singer Jennifer Lopez: 2 wds. |
| 42% | RINASAWAYAMA | 12 | Singer/songwriter and model who was one of "Vogue" Japan's 2019 women of the year (2 wds.) |
| 42% | ALGREEN | 7 | The Reverend ___ (soul singer in the Rock and Roll Hall of Fame): 2 wds. |
| 42% | PAULMCCARTNEY | 13 | One of the two singers on 15-Across: 2 wds. |
| 42% | STEVEWINWOOD | 12 | Singer who was part of the bands Traffic and the Spencer Davis Group: 2 wds. |
| 42% | SHIRLEYBASSEY | 13 | Singer of the James Bond theme songs "Goldfinger," "Diamonds Are Forever," and "Moonraker": 2 wds. |
| 42% | MARAINEY | 8 | Blues singer nicknamed "Mother of the Blues": 2 wds. |
| 41% | MRBIG | 5 | Nickname of Carrie's boyfriend on "Sex and the City": 2 wds. |
| 41% | CABCALLOWAY | 11 | Big-band leader and jazz singer whose signature song was "Minnie the Moocher": 2 wds. |
| 41% | GORDONSUMNER | 12 | 18-Across and 25-Across singer nicknamed "Sting" because of the black and yellow striped sweater he wore as a young performer (2 wds.) |
| 41% | BENNYGOODMAN | 12 | Big-band leader and jazz clarinetist called the "King of Swing": 2 wds. |
| 41% | ZAYNMALIK | 9 | One Direction singer who changed the spelling of his first name: 2 wds. |
| 41% | LUKEBRYAN | 9 | "Strip It Down" singer and 2015 CMA Entertainer of the Year: 2 wds. |
| 41% | EVAPERON | 8 | First lady of the 1940s and 1950s |
| 41% | JACKBLACK | 9 | "Jumanji: Welcome to the Jungle" actor and lead singer of the band Tenacious D: 2 wds. |
| 40% | MELC | 4 | Another nickname for Sporty Spice, one of the Spice Girls: 2 wds. |
| 40% | SHELLEYFABARES | 14 | Actress and singer who's the niece of 19-Across: 2 wds. |
| 40% | BILLIEEILISH | 12 | "Bad Guy" singer who received the Grammys for both Album of the Year and Best New Artist in 2020: 2 wds. |
| 40% | BILLIEEILISH | 12 | "Therefore I Am" singer who was one of the cohosts of the 2021 Met Gala: 2 wds. |