| 100% | NORAHJONES | 10 | "Don't Know Why" singer who has won nine Grammy Awards (2 wds.) |
| 60% | NORAHJONES | 10 | "Don't Know Why" singer who won the Best New Artist and Record of the Year Grammys in 2003: 2 wds. |
| 54% | ALISONKRAUSS | 12 | Bluegrass singer born July 23, 1971, who has won 27 Grammy Awards (2 wds.) |
| 52% | KATYPERRY | 9 | "Dark Horse" pop singer who has never won a Grammy despite 13 nominations: 2 wds. |
| 52% | NORAH | 5 | ___ Jones, "Don't Know Why" singer who was 23 when she won the 2003 Grammy for Record of the Year |
| 51% | MARTINAMCBRIDE | 14 | "In My Daughter's Eyes" country singer who has never won a Grammy despite 14 nominations: 2 wds. |
| 51% | JUSTINBIEBER | 12 | "Love Yourself" singer who has won the second-most Billboard Music Awards (21) (2 wds.) |
| 50% | LIZAMINNELLI | 12 | "Cabaret" star and singer who won one of the first Grammy Legend Awards, in 1990: 2 wds. |
| 50% | GARTHBROOKS | 11 | "Friends in Low Places" singer who has won the third-most Billboard Music Awards (19) (2 wds.) |
| 49% | SMOKEYROBINSON | 14 | "I Second That Emotion" singer who won one of the first Grammy Legend Awards, in 1990: 2 wds. |
| 49% | WILLIENELSON | 12 | "Always on My Mind" singer who won one of the first Grammy Legend Awards, in 1990: 2 wds. |
| 49% | TAYLORSWIFT | 11 | "Look What You Made Me Do" singer who has won the most Billboard Music Awards (23) (2 wds.) |
| 49% | KANYEWEST | 9 | Rapper/record producer who has won the second-most Grammy Awards among rappers (2 wds.) |
| 48% | STEVIEWONDER | 12 | "Superstition" singer who has won 25 Grammys: 2 wds. |
| 48% | AIMEEMANN | 9 | Grammy award winning female bassist who has been named one of the world's top ten greatest living songwriters by NPR: 2 wds. |
| 48% | ALISONKRAUSS | 12 | "Raising Sand" singer who won five Grammy Awards in 2009: 2 wds. |
| 47% | ART | 3 | Singer ___ Garfunkel who has won eight Grammy Awards |
| 47% | AMYWINEHOUSE | 12 | "Back to Black" singer who won five Grammy Awards in 2008: 2 wds. |
| 47% | RASCALFLATTS | 12 | "Yours If You Want It" singers who have won the Country Music Association Award for Vocal Group of the Year six times (2 wds.) |
| 46% | PRIYANKACHOPRA | 14 | Bollywood star who has won two People's Choice Awards: 2 wds. |
| 46% | ELVISCOSTELLO | 13 | "Look Now" singer who won the Best Traditional Pop Vocal Album Grammy Award in 2020 (2 wds.) |
| 46% | LADYGAGA | 8 | Singer who won a 2011 Grammy for "Bad Romance": 2 wds. |
| 46% | LILWAYNE | 8 | "Lollipop" rapper who's won five Grammy Awards: 2 wds. |
| 45% | BILLIEEILISH | 12 | "Bad Guy" singer who won a record five Grammy Awards in 2020, including Best New Artist (2 wds.) |
| 45% | MEGHANTRAINOR | 13 | 18-Across, 40-Across, and "All About That Bass" singer who has won two "Billboard" Music Awards and a "Billboard" Women in Music Chart-Topper Award (2 wds.) |
| 45% | JOHNWILLIAMS | 12 | Film music composer who has won 24 Grammy Awards, five Oscars, and four Golden Globes in the last six decades (2 wds.) |
| 45% | NATALIECOLE | 11 | "Unforgettable" singer who won the Best New Artist Grammy in 1976: 2 wds. |
| 44% | BRANDICARLILE | 13 | 18-Across and 42-Across singer who won a Best Country Song Grammy Award for "Bring My Flowers Now" (2 wds.) |
| 44% | LITTLEBIGTOWN | 13 | "Better Man" singers who have won the Country Music Association Award for Vocal Group of the Year six times (3 wds.) |
| 44% | ALISONKRAUSS | 12 | Singer who won her 27th Grammy for the 2011 bluegrass album "Paper Airplane": 2 wds. |