| 100% | JOHN | 4 | ___ Legend, American singer who won a Grammy for Best R&B Album in 2006 |
| 63% | BOB | 3 | ___ Dylan, American singer who won a Grammy for Album of the Year in 1973 |
| 57% | ROSS | 4 | Diana ___, American singer who won a Grammy for lifetime achievement award in 2012 |
| 56% | ADAMS | 5 | Bryan ___, Canadian singer who won a Grammy for Best Song Written for Visual Media in 1992 |
| 54% | TIFFANYHADDISH | 14 | "The Last O.G." actress who won a Grammy for Best Comedy Album in 2021: 2 wds. |
| 54% | DAVID | 5 | ___ Bowie, English singer who won a Grammy Award for best music video in 1985 |
| 54% | ENYA | 4 | Singer who won a Best New Age Album Grammy Award for "Amarantine" |
| 54% | KATHYGRIFFIN | 12 | "My Life on the D-List" star who won a Grammy for Best Comedy Album in 2014: 2 wds. |
| 53% | DANGELO | 7 | One-named R&B singer who won a Grammy for his 2014 album "Black Messiah" |
| 53% | PATTONOSWALT | 12 | "A.P. Bio" actor who won a Grammy for Best Comedy Album in 2017: 2 wds. |
| 52% | DAVIDBOWIE | 10 | Glam rock legend who won a posthumous Best Alternative Music Album Grammy in 2017 for "Blackstar": 2 wds. |
| 52% | HADDISH | 7 | Tiffany ___, "Black Mitzvah" comedian who won a Grammy Award for Best Comedy Album in 2021 |
| 51% | TIFFANYHADDISH | 14 | "Black Mitzvah" comedian who won a Grammy Award for Best Comedy Album in 2021 (2 wds.) |
| 51% | KATHYGRIFFIN | 12 | "Calm Down Gurrl" comedian who won a Grammy Award for Best Comedy Album in 2014 (2 wds.) |
| 51% | WHOOPIGOLDBERG | 14 | "Direct from Broadway" comedian who won a Grammy Award for Best Comedy Album in 1986 (2 wds.) |
| 51% | HILLARY | 7 | ___ Clinton, former First Lady who won a Grammy for Best Spoken Word album in 1997 |
| 50% | KACEY | 5 | Singer Musgraves who won a 2013 Grammy for Best Country Album |
| 50% | ERICA | 5 | Singer Campbell who won a Best Gospel Album Grammy Award for "Help" |
| 50% | FIONAAPPLE | 10 | Art pop singer-songwriter who won a Best Alternative Music Album Grammy in 2021 for "Fetch the Bolt Cutters": 2 wds. |
| 49% | JAZMINESULLIVAN | 15 | Singer whose “Heaux Tales” won the Grammy for Best R. & B. Album (April, 2022) |
| 49% | HER | 3 | Singer with a 2018 Grammy for Best R&B Album |
| 49% | GIRLONFIRE | 10 | Album by 40-Across that won a Grammy for Best R&B Album (3 wds.) |
| 47% | SHEERAN | 7 | Ed who won the Grammy for Best Pop Vocal Album in 2018 |
| 47% | RIHANNA | 7 | One-named singer who won the Grammy Award for Best Urban Contemporary Album for "Unapologetic" in 2014 |
| 46% | SEAN | 4 | ___ Paul, artist who won a Grammy for "Best Reggae Album" |
| 46% | WHOOPI | 6 | ___ Goldberg, comedian who won a Grammy Award for Best Comedy Recording in 1986 |
| 46% | OLIVIARODRIGO | 13 | "Drivers License" singer who won a Best New Artist Grammy in 2022: 2 wds. |
| 46% | BILLIE | 6 | With 34-Across, "Bad Guy" singer who won a Best New Artist Grammy in 2020 |
| 45% | TRAVISSCOTT | 11 | Rapper who was nominated for a Grammy for Best Rap Album in 2019 but lost to Cardi B: 2 wds. |
| 45% | MEGHANTRAINOR | 13 | "All About That Bass" singer who won a Best New Artist Grammy in 2016: 2 wds. |