| 100% | MIRANDALAMBERT | 14 | Singer whose "Wildcard" won the Grammy for Best Country Album in 2021: 2 wds. |
| 82% | CHRISSTAPLETON | 14 | Singer whose "Starting Over" won the Grammy for Best Country Album in 2022: 2 wds. |
| 62% | WILLIE | 6 | With 39-Across, singer whose "A Beautiful Time" won the Grammy for Best Country Album in 2023 |
| 60% | TIFFANYHADDISH | 14 | "The Last O.G." actress who won a Grammy for Best Comedy Album in 2021: 2 wds. |
| 60% | ANDREABOCELLI | 13 | Italian classical singer whose album "Cinema" was nominated for Best Traditional Pop Vocal Album in the 2017 Grammy Awards : 2 wds. |
| 58% | FIONAAPPLE | 10 | Art pop singer-songwriter who won a Best Alternative Music Album Grammy in 2021 for "Fetch the Bolt Cutters": 2 wds. |
| 58% | MICHELLEZAUNER | 14 | Singer whose memoir "Crying in H Mart" won the 2021 Goodreads Choice Award for Best Memoir & Autobiography (2 wds.) |
| 57% | TRACYCHAPMAN | 12 | "Fast Car" singer who won the Grammy for Best New Artist in 1989: 2 wds. |
| 57% | JUSTINBIEBER | 12 | Singer whose "Peaches" won the MTV Video Music Award for Best Pop Video in 2021: 2 wds. |
| 55% | THEWARONDRUGS | 13 | Band which won the Grammy for Best Rock Album in 2018: 4 wds. |
| 54% | PATTYLOVELESS | 13 | "Blame It on Your Heart" singer whose "Mountain Soul II" won the Best Bluegrass Album Grammy in 2011: 2 wds. |
| 54% | CYNDILAUPER | 11 | "Girls Just Wanna Have Fun" singer who won the Grammy for Best New Artist in 1985: 2 wds. |
| 52% | KATHYGRIFFIN | 12 | "My Life on the D-List" star who won a Grammy for Best Comedy Album in 2014: 2 wds. |
| 51% | IWANTED | 7 | "Everything ___," song by Billie Eilish which won the Grammy for Record of the Year in 2021: 2 wds. |
| 51% | STAYHIGH | 8 | Brittany Howard song that won the Grammy Award for Best Rock Song in 2021: 2 wds. |
| 51% | AIMEEMANN | 9 | Former 'Til Tuesday lead singer whose "Mental Illness" won Best Folk Album at the 2018 Grammy Awards (2 wds.) |
| 51% | CULTURECLUB | 11 | "Karma Chameleon" band that won the Grammy for Best New Artist in 1984: 2 wds. |
| 51% | TIFFANYHADDISH | 14 | "Black Mitzvah" comedian who won a Grammy Award for Best Comedy Album in 2021 (2 wds.) |
| 50% | TAYLORSWIFT | 11 | Singer-songwriter whose "1989" won 2016's Grammy Award for Album of the Year (2 wds.) |
| 50% | JENNIFERHUDSON | 14 | Singer who won the Oscar for Best Performance in a Supporting Role for "Dreamgirls": 2 wds. |
| 49% | PATTONOSWALT | 12 | "A.P. Bio" actor who won a Grammy for Best Comedy Album in 2017: 2 wds. |
| 49% | ALWAYSONMYMIND | 14 | 28-/40-Across hit that won the Grammy for Best Country Song in 1983: 4 wds. |
| 49% | ONTHEROADAGAIN | 14 | 28-/40-Across hit that won the Grammy for Best Country Song in 1981: 4 wds. |
| 49% | JAZMINESULLIVAN | 15 | Singer whose “Heaux Tales” won the Grammy for Best R. & B. Album (April, 2022) |
| 49% | SHEERAN | 7 | Ed who won the Grammy for Best Pop Vocal Album in 2018 |
| 49% | SHAKIRA | 7 | One-named singer whose album "El Dorado" won the 2018 Grammy Award for Best Latin Pop Album |
| 48% | LAINEYWILSON | 12 | "Bell Bottom Country" singer who won Best Country Album at the 2024 Grammy Awards (2 wds.) |
| 48% | BLACK | 5 | "___ Parade," single by Beyonce which won the Grammy for Best R&B Performance in 2021 |
| 47% | THEWEEKND | 9 | Singer with an oddly spelled name whose "Starboy" won Best Urban Contemporary Album at the 2018 Grammy Awards (2 wds.) |
| 47% | ADELEADKINS | 11 | British singer whose third studio album fetched her the Album of the Year in the 2017 Grammy Awards : 2 wds. |