| 100% | AIMEEMANN | 9 | Former 'Til Tuesday lead singer whose "Mental Illness" won Best Folk Album at the 2018 Grammy Awards (2 wds.) |
| 54% | THEWEEKND | 9 | Singer with an oddly spelled name whose "Starboy" won Best Urban Contemporary Album at the 2018 Grammy Awards (2 wds.) |
| 49% | LAINEYWILSON | 12 | "Bell Bottom Country" singer who won Best Country Album at the 2024 Grammy Awards (2 wds.) |
| 47% | EDSHEERAN | 9 | "Shape of You" singer who won two awards, including Best Pop Vocal Album, at the 2018 Grammy Awards (2 wds.) |
| 46% | LOEB | 4 | Singer Lisa whose "Feel What U Feel" won Best Children's Album at the 2018 Grammy Awards |
| 46% | CELINEDION | 10 | Singer whose 1996 album "Falling into You" won Grammy Awards for Album of the Year and Best Pop Album (2 wds.) |
| 45% | MIRANDALAMBERT | 14 | Singer whose "Wildcard" won the Grammy for Best Country Album in 2021: 2 wds. |
| 44% | CHRISSTAPLETON | 14 | Singer whose "Starting Over" won the Grammy for Best Country Album in 2022: 2 wds. |
| 43% | CARA | 4 | Singer Alessia who won Best New Artist at the 2018 Grammy Awards |
| 43% | PATTYLOVELESS | 13 | "Blame It on Your Heart" singer whose "Mountain Soul II" won the Best Bluegrass Album Grammy in 2011: 2 wds. |
| 41% | VICTORIAMONET | 13 | "Jaguar II" singer who won Best R&B album and Best New Artist at the 2024 Grammy Awards (2 wds.) |
| 39% | SHAKIRA | 7 | One-named singer whose album "El Dorado" won the 2018 Grammy Award for Best Latin Pop Album |
| 39% | HARRYSTYLES | 11 | Singer whose "As It Was" won the MTV Video Music Award for Best Pop Video in 2022: 2 wds. |
| 39% | JUSTINBIEBER | 12 | Singer whose "Peaches" won the MTV Video Music Award for Best Pop Video in 2021: 2 wds. |
| 38% | TAYLORSWIFT | 11 | Singer whose "Anti-Hero" won the MTV Video Music Award for Best Pop Video in 2023: 2 wds. |
| 37% | FOOFIGHTERS | 11 | Band whose "Run" won the 2018 Grammy for Best Rock Song: 2 wds. |
| 37% | BRUNOMARS | 9 | "24K Magic" singer who won six awards, including Record of the Year, at the 2018 Grammy Awards (2 wds.) |
| 37% | TAYLORSWIFT | 11 | Singer-songwriter whose "1989" won 2016's Grammy Award for Album of the Year (2 wds.) |
| 37% | MORNINGPHASE | 12 | Beck album that won the 2015 Grammy Award for Best Rock Album: 2 wds. |
| 37% | THERESISTANCE | 13 | Muse album that won the 2011 Grammy Award for Best Rock Album: 2 wds. |
| 37% | MICHELLEZAUNER | 14 | Singer whose memoir "Crying in H Mart" won the 2021 Goodreads Choice Award for Best Memoir & Autobiography (2 wds.) |
| 36% | WASTINGLIGHT | 12 | Foo Fighters album that won the 2012 Grammy Award for Best Rock Album: 2 wds. |
| 36% | ANDREABOCELLI | 13 | Italian classical singer whose album "Cinema" was nominated for Best Traditional Pop Vocal Album in the 2017 Grammy Awards : 2 wds. |
| 35% | IGOR | 4 | Tyler, the Creator album that won Best Rap Album at the 2020 Grammy Awards |
| 35% | BILLIEEILISH | 12 | Grammy Award-winning singer with the new album "Happier Than Ever" (2 wds.) |
| 35% | DOLLYPARTON | 11 | "9 to 5" actress/singer whose "The Grass Is Blue" won the Best Bluegrass Album Grammy in 2001: 2 wds. |
| 35% | TRUTHHURTS | 10 | 1-Across hit that won Best Pop Solo Performance at the 2020 Grammy Awards: 2 wds. |
| 35% | JAZMINESULLIVAN | 15 | Singer whose “Heaux Tales” won the Grammy for Best R. & B. Album (April, 2022) |
| 34% | BEYONCE | 7 | 14-Across, 8-Down, and 49-Across singer whose "Cowboy Carter" won Album of the Year at the Grammy Awards in 2025 |
| 34% | NEYO | 4 | Singer whose song won a Grammy award for the Best R&B Song "Miss Independent:" Hyph. |