| 100% | FIONAAPPLE | 10 | Art pop singer-songwriter who won a Best Alternative Music Album Grammy in 2021 for "Fetch the Bolt Cutters": 2 wds. |
| 54% | VAMPIREWEEKEND | 14 | Indie rock band that won a Best Alternative Music Album Grammy in 2020 for "Father of the Bride": 2 wds. |
| 51% | DAVIDBOWIE | 10 | Glam rock legend who won a posthumous Best Alternative Music Album Grammy in 2017 for "Blackstar": 2 wds. |
| 48% | TIFFANYHADDISH | 14 | "The Last O.G." actress who won a Grammy for Best Comedy Album in 2021: 2 wds. |
| 45% | TIFFANYHADDISH | 14 | "Black Mitzvah" comedian who won a Grammy Award for Best Comedy Album in 2021 (2 wds.) |
| 43% | MIRANDALAMBERT | 14 | Singer whose "Wildcard" won the Grammy for Best Country Album in 2021: 2 wds. |
| 42% | PATTONOSWALT | 12 | "A.P. Bio" actor who won a Grammy for Best Comedy Album in 2017: 2 wds. |
| 42% | JUSTINBIEBER | 12 | Singer whose "Peaches" won the MTV Video Music Award for Best Pop Video in 2021: 2 wds. |
| 41% | KATHYGRIFFIN | 12 | "My Life on the D-List" star who won a Grammy for Best Comedy Album in 2014: 2 wds. |
| 41% | ELVISCOSTELLO | 13 | "Look Now" singer who won the Best Traditional Pop Vocal Album Grammy Award in 2020 (2 wds.) |
| 41% | JENNIFERHUDSON | 14 | Singer who won the Oscar for Best Performance in a Supporting Role for "Dreamgirls": 2 wds. |
| 41% | BURTONCUMMINGS | 14 | Singer-songwriter in the Canadian Music Hall of Fame who won the 1979 Album of the Year Juno Award for "Dream of a Child" (2 wds.) |
| 41% | JOELGREY | 8 | Singer/actor who won a Best Supporting Actor Oscar for playing the Master of Ceremonies in the 1972 film "Cabaret" (2 wds.) |
| 40% | KATHYGRIFFIN | 12 | "Calm Down Gurrl" comedian who won a Grammy Award for Best Comedy Album in 2014 (2 wds.) |
| 40% | WHOOPIGOLDBERG | 14 | "Direct from Broadway" comedian who won a Grammy Award for Best Comedy Album in 1986 (2 wds.) |
| 40% | TRACYCHAPMAN | 12 | "Fast Car" singer who won the Grammy for Best New Artist in 1989: 2 wds. |
| 39% | SAMSMITH | 8 | "Love Goes" singer who won the GLAAD Media Award for Outstanding Music Artist in 2021: 2 wds. |
| 39% | SHAWNMENDES | 11 | "Señorita" singer who won Canada's Juno Award for Pop Album of the Year in 2019: 2 wds. |
| 39% | HADDISH | 7 | Tiffany ___, "Black Mitzvah" comedian who won a Grammy Award for Best Comedy Album in 2021 |
| 38% | SHEERAN | 7 | Ed who won the Grammy for Best Pop Vocal Album in 2018 |
| 38% | RACHELMADDOW | 12 | MSNBC host who won a 2021 Grammy for the audiobook of her nonfiction book "Blowout": 2 wds. |
| 38% | ALICIAKEYS | 10 | "Songs in A Minor" singer/songwriter who won the 2021 Audie Award for Narration by the Author for her memoir "More Myself" (2 wds.) |
| 38% | LIZAMINNELLI | 12 | Singer/actress who won a Best Actress Oscar for playing Sally Bowles in "Cabaret" (2 wds.) |
| 38% | HARRY | 5 | ___ Styles, "Watermelon Sugar" singer who won the Grammy for Best Pop Solo Performance in 2021 |
| 38% | STEVEMARTIN | 11 | "The Jerk" actor whose first solo music album, "The Crow: New Songs for the 5-String Banjo" won a Grammy for Best Bluegrass Album: 2 wds. |
| 38% | OLIVIARODRIGO | 13 | "Drivers License" singer who won a Best New Artist Grammy in 2022: 2 wds. |
| 38% | KATRINALENK | 11 | 30-Across singer/actress who won the 2018 Tony Award for Best Actress in a Musical (2 wds.) |
| 37% | CYNDILAUPER | 11 | "Girls Just Wanna Have Fun" singer who won the Grammy for Best New Artist in 1985: 2 wds. |
| 37% | HOLLYHUNTER | 11 | "Broadcast News" star who won a Best Actress Oscar for her role in "The Piano": 2 wds. |
| 37% | ALISONKRAUSS | 12 | Singer who won her 27th Grammy for the 2011 bluegrass album "Paper Airplane": 2 wds. |