| 100% | SHEERAN | 7 | Ed who won the Grammy for Best Pop Vocal Album in 2018 |
| 60% | ALESSIA | 7 | Cara who won the Grammy for Best New Artist in 2018 |
| 59% | ELVISCOSTELLO | 13 | "Look Now" singer who won the Best Traditional Pop Vocal Album Grammy Award in 2020 (2 wds.) |
| 58% | THEWARONDRUGS | 13 | Band which won the Grammy for Best Rock Album in 2018: 4 wds. |
| 57% | SOUR | 4 | Album by Olivia Rodrigo that won the Grammy Award for Best Pop Vocal Album in 2022 |
| 54% | RIHANNA | 7 | One-named singer who won the Grammy Award for Best Urban Contemporary Album for "Unapologetic" in 2014 |
| 54% | HARRY | 5 | ___ Styles, "Watermelon Sugar" singer who won the Grammy for Best Pop Solo Performance in 2021 |
| 53% | EDSHEERAN | 9 | "Shape of You" singer who won two awards, including Best Pop Vocal Album, at the 2018 Grammy Awards (2 wds.) |
| 53% | LYNNE | 5 | Shelby who won the Grammy for Best New Artist in 2001 |
| 53% | EDDIE | 5 | ___ Murphy, comedian who won the Grammy for Best Comedy Recording in 1984 |
| 52% | THEWEEKND | 9 | 16-Across and 34-Across singer who won the 2018 Best Urban Contemporary Album Grammy for "Starboy" (2 wds.) |
| 52% | TRACYCHAPMAN | 12 | "Fast Car" singer who won the Grammy for Best New Artist in 1989: 2 wds. |
| 51% | FIONAAPPLE | 10 | Art pop singer-songwriter who won a Best Alternative Music Album Grammy in 2021 for "Fetch the Bolt Cutters": 2 wds. |
| 51% | CYNDILAUPER | 11 | "Girls Just Wanna Have Fun" singer who won the Grammy for Best New Artist in 1985: 2 wds. |
| 50% | MIRANDALAMBERT | 14 | Singer whose "Wildcard" won the Grammy for Best Country Album in 2021: 2 wds. |
| 50% | CHRISSTAPLETON | 14 | Singer whose "Starting Over" won the Grammy for Best Country Album in 2022: 2 wds. |
| 49% | WILLIE | 6 | With 39-Across, singer whose "A Beautiful Time" won the Grammy for Best Country Album in 2023 |
| 48% | DRAKE | 5 | Rapper who won the Grammy Award for Best Rap Song in 2017 for "Hotline Bling" |
| 48% | LAMAR | 5 | Kendrick ___, rapper who won the Grammy Award for Best Rap Song in 2016 for "Alright" |
| 48% | EMINEM | 6 | Rapper who won the Grammy Award for Best Rap Song in 2004 for "Lose Yourself" |
| 48% | OLIVIA | 6 | ___ Rodrigo, "Drivers License" singer who won the Grammy Award for Best New Artist in 2022 |
| 48% | LYLE | 4 | Musician Lovett who won the Best Country Album Grammy in 1996 |
| 48% | WEST | 4 | Kanye ___, rapper who won the Grammy Award for Best Rap Song in 2005 for "Jesus Walks" |
| 48% | JON | 3 | ___ Batiste, "We Are" singer who won the Grammy Award for Album of the Year in 2022 |
| 48% | JAY | 3 | ___-Z, rapper who won the Grammy Award for Best Rap Song in 2010 for "Run This Town" |
| 47% | ADELE | 5 | British singer who won the Album of the Year Grammy in 2012 for "21" |
| 47% | KATHYGRIFFIN | 12 | "My Life on the D-List" star who won a Grammy for Best Comedy Album in 2014: 2 wds. |
| 46% | TIFFANYHADDISH | 14 | "The Last O.G." actress who won a Grammy for Best Comedy Album in 2021: 2 wds. |
| 46% | JOHN | 4 | ___ Legend, American singer who won a Grammy for Best R&B Album in 2006 |
| 46% | IRENE | 5 | Singer Cara who won a Grammy for best female pop vocal performance for "Flashdance ... What a Feeling" |