| 100% | STEVEMARTIN | 11 | "L.A. Story" actor whose "The Crow: New Songs for the 5-String Banjo" won the Best Bluegrass Album Grammy in 2010: 2 wds. |
| 73% | 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. |
| 49% | DOLLYPARTON | 11 | "9 to 5" actress/singer whose "The Grass Is Blue" won the Best Bluegrass Album Grammy in 2001: 2 wds. |
| 48% | PATTYLOVELESS | 13 | "Blame It on Your Heart" singer whose "Mountain Soul II" won the Best Bluegrass Album Grammy in 2011: 2 wds. |
| 44% | PATTONOSWALT | 12 | "A.P. Bio" actor who won a Grammy for Best Comedy Album in 2017: 2 wds. |
| 43% | MIRANDALAMBERT | 14 | Singer whose "Wildcard" won the Grammy for Best Country Album in 2021: 2 wds. |
| 43% | KATHYGRIFFIN | 12 | "My Life on the D-List" star who won a Grammy for Best Comedy Album in 2014: 2 wds. |
| 42% | CHRISSTAPLETON | 14 | Singer whose "Starting Over" won the Grammy for Best Country Album in 2022: 2 wds. |
| 42% | VAMPIREWEEKEND | 14 | Indie rock band that won a Best Alternative Music Album Grammy in 2020 for "Father of the Bride": 2 wds. |
| 42% | TONIBRAXTON | 11 | "Another Sad Love Song" singer who won the Best New Artist Grammy in 1994: 2 wds. |
| 42% | FIONAAPPLE | 10 | Art pop singer-songwriter who won a Best Alternative Music Album Grammy in 2021 for "Fetch the Bolt Cutters": 2 wds. |
| 41% | TIFFANYHADDISH | 14 | "The Last O.G." actress who won a Grammy for Best Comedy Album in 2021: 2 wds. |
| 41% | SAYSOMETHING | 12 | Song for which A Great Big World and Christina Aguilera won the Grammy for Best Pop Duo/Group Performance in 2015: 2 wds. |
| 40% | STRESSEDOUT | 11 | Song for which Twenty One Pilots won the Grammy for Best Pop Duo/Group Performance in 2017: 2 wds. |
| 40% | FOOFIGHTERS | 11 | Band whose "Run" won the 2018 Grammy for Best Rock Song: 2 wds. |
| 39% | VAMPIREWEEKEND | 14 | New York City rock band whose last two albums each won the Grammy Award for Best Alternative Music Album (2 wds.) |
| 39% | INCHNAILS | 9 | Nine ___, band whose song "Wish" won the 1993 Grammy for Best Metal Performance: 2 wds. |
| 39% | ALABAMASHAKES | 13 | Band whose "Don't Wanna Fight" won the 2016 Grammy for Best Rock Song: 2 wds. |
| 39% | KINGSOFLEON | 11 | Band whose "Use Somebody" won the 2010 Grammy for Best Rock Song: 3 wds. |
| 39% | NATALIECOLE | 11 | "Unforgettable" singer who won the Best New Artist Grammy in 1976: 2 wds. |
| 38% | DAVIDBOWIE | 10 | Glam rock legend who won a posthumous Best Alternative Music Album Grammy in 2017 for "Blackstar": 2 wds. |
| 38% | SARAHPAULSON | 12 | "American Horror Story" actress who won the 2024 Best Leading Actress in a Play Tony for "Appropriate": 2 wds. |
| 38% | JOSHOCONNOR | 11 | "The Crown" actor who won the 2021 Emmy for Outstanding Lead Actor in a Drama Series: 2 wds. |
| 38% | TRACYCHAPMAN | 12 | "Fast Car" singer who won the Grammy for Best New Artist in 1989: 2 wds. |
| 38% | CULTURECLUB | 11 | "Karma Chameleon" band that won the Grammy for Best New Artist in 1984: 2 wds. |
| 38% | MARIAHCAREY | 11 | "Vision of Love" singer who won the Best New Artist Grammy in 1991: 2 wds. |
| 38% | STAYHIGH | 8 | Brittany Howard song that won the Grammy Award for Best Rock Song in 2021: 2 wds. |
| 38% | BETTEMIDLER | 11 | "Wind Beneath My Wings" singer who won the Best New Artist Grammy in 1974: 2 wds. |
| 38% | CARLYSIMON | 10 | "You're So Vain" singer who won the Best New Artist Grammy in 1972: 2 wds. |
| 38% | ZACBROWNBAND | 12 | American country music band with the hit song "Colder Weather", that won the 2010 Grammy for Best New Artist: 3 wds. |