| 100% | ELLAFITZGERALD | 14 | Jazz singer nicknamed "Queen of Jazz" and "First Lady of Song": 2 wds. |
| 60% | SARAHVAUGHAN | 12 | Jazz singer of the 1940s and 1950s nicknamed "The Divine One": 2 wds. |
| 54% | FRANKSINATRA | 12 | Jazz crooner nicknamed "Chairman of the Board" and "Ol' Blue Eyes": 2 wds. |
| 54% | JLO | 3 | Nickname of actress and singer Jennifer Lopez: 2 wds. |
| 53% | ELLAFITZGERALD | 14 | "The First Lady of Song," who would have turned 100 next Tuesday: 2 wds. |
| 52% | ELLA | 4 | ___ Fitzgerald, singer dubbed the "First Lady of Song" with 14 Grammy Awards and is considered one of the most influential figures in jazz |
| 51% | HELENHAYES | 10 | American actress nicknamed "First Lady of American Theatre" who has won the EGOT (Emmy, Grammy, Oscar, and Tony): 2 wds. |
| 50% | GLORIAESTEFAN | 13 | "Conga" singer nicknamed "The Queen of Latin Pop": 2 wds. |
| 50% | CABCALLOWAY | 11 | Big-band leader and jazz singer whose signature song was "Minnie the Moocher": 2 wds. |
| 50% | DIONNEWARWICK | 13 | Singer of many Burt Bacharach songs, including 34- and 44-Across: 2 wds. |
| 49% | MICHELLEOBAMA | 13 | First Lady known for her support of military families and healthy eating: 2 wds. |
| 49% | TINATURNER | 10 | "Private Dancer" singer nicknamed "The Queen of Rock 'n' Roll": 2 wds. |
| 49% | JLO | 3 | Nickname of the singer known for "All I Have" and "On the Floor": 2 wds. |
| 49% | SHIRLEYBASSEY | 13 | Singer of the James Bond theme songs "Goldfinger," "Diamonds Are Forever," and "Moonraker": 2 wds. |
| 47% | ELLA | 4 | ___ Fitzgerald, jazz legend sometimes referred to as "The First Lady of Song" |
| 47% | EDSHEERAN | 9 | English singer whose album "÷" and song "Shape of You" both topped the charts in 2017: 2 wds. |
| 47% | LIZAMINNELLI | 12 | "Cabaret" star and singer who won one of the first Grammy Legend Awards, in 1990: 2 wds. |
| 46% | STEVIENICKS | 11 | American singer and songwriter who became the first woman to be inducted twice into the Rock and Roll Hall of Fame: 2 wds. |
| 46% | SARAHVAUGHAN | 12 | Jazz vocalist nicknamed "The Divine One" and "Sassy": 2 wds. |
| 45% | MICHELLEOBAMA | 13 | First Lady of the United States (2009-2017) who wrote "Becoming": 2 wds. |
| 45% | DIANAROSS | 9 | American singer who was the lead singer of "The Supremes" and is known for her solo songs like "Upside Down": 2 wds. |
| 45% | MICHELLEOBAMA | 13 | Former First Lady and "Becoming" author who was on the cover of the Winter 2021/22 issue of Vogue Knitting: 2 wds. |
| 44% | MICHELLE | 8 | Beatles song and name of a US first lady |
| 44% | MARAINEY | 8 | Blues singer nicknamed "Mother of the Blues": 2 wds. |
| 44% | KELLYCLARKSON | 13 | Singer of the 2015 hit "Heartbeat Song": 2 wds. |
| 44% | RACHELPLATTEN | 13 | Singer of the 2015 hit "Fight Song": 2 wds. |
| 44% | SARABAREILLES | 13 | Singer of the 2007 hit "Love Song": 2 wds. |
| 44% | 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. |
| 44% | LADYBIRD | 8 | First Lady Johnson's nickname: 2 wds. |
| 44% | WEIRDAL | 7 | Nickname of parody singer Yankovic: 2 wds. |