| 100% | ANDERSONPAAK | 12 | LA hip-hop artist who won a 2019 Grammy for Best Rap Performance for "Bubblin": 2 wds. |
| 72% | NIPSEYHUSSLE | 12 | Late LA hip-hop artist nominated for a 2019 Grammy for Best Rap Album for "Victory Lap": 2 wds. |
| 54% | KENDRICKLAMAR | 13 | LA hip-hop artist who was nominated for eight Grammys in 2019: 2 wds. |
| 53% | TRAVISSCOTT | 11 | Rapper who was nominated for a Grammy for Best Rap Album in 2019 but lost to Cardi B: 2 wds. |
| 52% | CARDI | 5 | ___ B, hip hop star who became the first female rapper to win a Grammy for Best Rap Album |
| 50% | MACMILLER | 9 | Artist who was posthumously nominated for a Best Rap Album Grammy in 2019 |
| 50% | BRYANCRANSTON | 13 | "Network" actor who won the Tony Award for Best Performance by a Leading Actor in a Play in 2019 (2 wds.) |
| 49% | TIFFANYHADDISH | 14 | "Black Mitzvah" comedian who won a Grammy Award for Best Comedy Album in 2021 (2 wds.) |
| 49% | ELAINEMAY | 9 | "The Waverly Gallery" actress who won the Tony Award for Best Performance by a Leading Actress in a Play in 2019 (2 wds.) |
| 49% | TIFFANYHADDISH | 14 | "The Last O.G." actress who won a Grammy for Best Comedy Album in 2021: 2 wds. |
| 49% | KATHYGRIFFIN | 12 | "Calm Down Gurrl" comedian who won a Grammy Award for Best Comedy Album in 2014 (2 wds.) |
| 49% | WHOOPIGOLDBERG | 14 | "Direct from Broadway" comedian who won a Grammy Award for Best Comedy Album in 1986 (2 wds.) |
| 49% | PATTONOSWALT | 12 | "A.P. Bio" actor who won a Grammy for Best Comedy Album in 2017: 2 wds. |
| 49% | CARDIB | 6 | First woman to win a Grammy for Best Rap Album as a solo artist (2 wds.) |
| 48% | OLIVIARODRIGO | 13 | "Drivers License" singer who won a Best New Artist Grammy in 2022: 2 wds. |
| 47% | KATHYGRIFFIN | 12 | "My Life on the D-List" star who won a Grammy for Best Comedy Album in 2014: 2 wds. |
| 47% | TRACYCHAPMAN | 12 | "Fast Car" singer who won the Grammy for Best New Artist in 1989: 2 wds. |
| 47% | MEGHANTRAINOR | 13 | "All About That Bass" singer who won a Best New Artist Grammy in 2016: 2 wds. |
| 46% | CYNDILAUPER | 11 | "Girls Just Wanna Have Fun" singer who won the Grammy for Best New Artist in 1985: 2 wds. |
| 46% | DAVIDBOWIE | 10 | Glam rock legend who won a posthumous Best Alternative Music Album Grammy in 2017 for "Blackstar": 2 wds. |
| 46% | CARDIB | 6 | "Up" rapper who won the American Music Award for Favorite Rap/Hip-Hop Artist twice: 2 wds. |
| 46% | LADYGAGA | 8 | Singer who won a 2011 Grammy for "Bad Romance": 2 wds. |
| 46% | TAYLORSWIFT | 11 | Singer who was nominated for a Grammy for Best New Artist in 2008 but lost to Amy Winehouse: 2 wds. |
| 46% | FAMILYTIES | 10 | 2021 Baby Keem and Kendrick Lamar hit that won a Grammy for Rap Performance: 2 wds. |
| 46% | JENNIFERHUDSON | 14 | Singer who won the Oscar for Best Performance in a Supporting Role for "Dreamgirls": 2 wds. |
| 45% | FIONAAPPLE | 10 | Art pop singer-songwriter who won a Best Alternative Music Album Grammy in 2021 for "Fetch the Bolt Cutters": 2 wds. |
| 45% | MACKLEMORE | 10 | Artist on NBC's "Songland" whose "The Heist," with Ryan Lewis, won a 2014 Grammy for best rap album |
| 45% | BETTERMAN | 9 | 2016 song written by Taylor Swift and performed by 33-Across that won a Grammy Award for Best Country Duo/Group Performance (2 wds.) |
| 45% | NICKIMINAJ | 10 | "Anaconda" rapper who won the American Music Award for Favorite Rap/Hip-Hop Artist four times: 2 wds. |
| 45% | IGGYAZALEA | 10 | "Fancy" rapper who won the American Music Award for Favorite Rap/Hip-Hop Artist in 2014: 2 wds. |