| 100% | BUDDYGUY | 8 | Blues guitarist/singer whom Eric Clapton described as "the best guitar player alive": 2 wds. |
| 36% | ROBERTJOHNSON | 13 | Blues guitarist who wrote such classics as "Cross Road Blues": 2 wds. |
| 36% | LENAHORNE | 9 | Singer who played Glinda the Good Witch in "The Wiz": 2 wds. |
| 35% | MARIAHCAREY | 11 | "Vision of Love" singer who won the Best New Artist Grammy in 1991: 2 wds. |
| 35% | TRACYCHAPMAN | 12 | "Fast Car" singer who won the Grammy for Best New Artist in 1989: 2 wds. |
| 35% | BESSIESMITH | 11 | Harlem Renaissance singer who starred in the 1929 short film "St. Louis Blues": 2 wds. |
| 35% | NATALIECOLE | 11 | "Unforgettable" singer who won the Best New Artist Grammy in 1976: 2 wds. |
| 35% | DEMILOVATO | 10 | "Camp Rock!" actress and singer who plays the piano and guitar: 2 wds. |
| 35% | JENNIFERHUDSON | 14 | Singer who won the Oscar for Best Performance in a Supporting Role for "Dreamgirls": 2 wds. |
| 35% | DUALIPA | 7 | "New Rules" singer who describes Coldplay frontman Chris Martin as a "mentor": 2 wds. |
| 34% | LIONELRICHIE | 12 | Singer who won the Oscar in 1986 for Best Original Song, "Say You, Say Me": 2 wds. |
| 34% | STEVIEWONDER | 12 | Singer who won the Oscar for Best Original Song, "Just Called to Say I Love You": 2 wds. |
| 34% | BETTEMIDLER | 11 | "Wind Beneath My Wings" singer who won the Best New Artist Grammy in 1974: 2 wds. |
| 34% | CARLYSIMON | 10 | "You're So Vain" singer who won the Best New Artist Grammy in 1972: 2 wds. |
| 34% | TONIBRAXTON | 11 | "Another Sad Love Song" singer who won the Best New Artist Grammy in 1994: 2 wds. |
| 34% | DEBBYBOONE | 10 | "You Light Up My Life" singer who won the Best New Artist Grammy in 1978: 2 wds. |
| 34% | VICTORIAMONET | 13 | "On My Mama" R&B singer who won Best New Artist at the 2024 Grammys: 2 wds. |
| 34% | NOAHKAHAN | 9 | "Hurt Somebody" rock singer who was nominated for Best New Artist at the 2024 Grammys: 2 wds. |
| 33% | NICKLACHEY | 10 | 98 Degrees lead singer who won the fifth season of "The Masked Singer" as the Piglet: 2 wds. |
| 33% | JELLYROLL | 9 | "Need a Favor" country singer who was nominated for Best New Artist at the 2024 Grammys: 2 wds. |
| 33% | CYNDILAUPER | 11 | "Girls Just Wanna Have Fun" singer who won the Grammy for Best New Artist in 1985: 2 wds. |
| 33% | LEANNRIMES | 10 | "How Do I Live" singer who won the fourth season of "The Masked Singer" as the Sun: 2 wds. |
| 33% | GLENCAMPBELL | 12 | "Rhinestone Cowboy" singer who recently won the Best Country Song Grammy: 2 wds. |
| 32% | BILLIEEILISH | 12 | "Bad Guy" singer who received the Grammys for both Album of the Year and Best New Artist in 2020: 2 wds. |
| 32% | LAURYNHILL | 10 | "Everything Is Everything" singer who received the Grammys for both Album of the Year and Best New Artist in 1999: 2 wds. |
| 32% | MICHAELSTIPE | 12 | Singer who came up with "It's the End of the World as We Know It (And I Feel Fine)" in his sleep: 2 wds. |
| 32% | 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. |
| 32% | LADYGAGA | 8 | "Born This Way" singer who guest-starred as herself on "The Simpsons": 2 wds. |
| 31% | LAINEYWILSON | 12 | "Bell Bottom Country" singer who won Best Country Album at the 2024 Grammy Awards (2 wds.) |
| 31% | ERICCLAPTON | 11 | English rock and blues guitarist who is the only artist to be inducted three times into the Rock and Roll Hall of Fame: 2 wds. |