| 100% | HARRY | 5 | ___ Styles, "Watermelon Sugar" singer who won the Grammy for Best Pop Solo Performance in 2021 |
| 62% | YOU | 3 | "Someone like ___," hit song by Adele that won the Grammy for Best Pop Solo Performance in 2012 |
| 53% | TRACYCHAPMAN | 12 | "Fast Car" singer who won the Grammy for Best New Artist in 1989: 2 wds. |
| 53% | SHEERAN | 7 | Ed who won the Grammy for Best Pop Vocal Album in 2018 |
| 52% | CYNDILAUPER | 11 | "Girls Just Wanna Have Fun" singer who won the Grammy for Best New Artist in 1985: 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% | JENNIFERHUDSON | 14 | Singer who won the Oscar for Best Performance in a Supporting Role for "Dreamgirls": 2 wds. |
| 50% | OLIVIA | 6 | ___ Rodrigo, "Drivers License" singer who won the Grammy Award for Best New Artist in 2022 |
| 50% | RIHANNA | 7 | One-named singer who won the Grammy Award for Best Urban Contemporary Album for "Unapologetic" in 2014 |
| 49% | LONG | 4 | Muni ___, "Hrs & Hrs" female singer who won the 2023 Grammy for Best R&B Performance |
| 48% | ELVISCOSTELLO | 13 | "Look Now" singer who won the Best Traditional Pop Vocal Album Grammy Award in 2020 (2 wds.) |
| 48% | MIRANDALAMBERT | 14 | Singer whose "Wildcard" won the Grammy for Best Country Album in 2021: 2 wds. |
| 48% | TRUTH | 5 | "___ Hurts," song by Lizzo that won the Grammy Award for Best Pop Solo Performance in 2020 |
| 48% | IRENE | 5 | Singer Cara who won a Grammy for best female pop vocal performance for "Flashdance ... What a Feeling" |
| 47% | BLACK | 5 | "___ Parade," single by Beyonce which won the Grammy for Best R&B Performance in 2021 |
| 47% | ALESSIA | 7 | Cara who won the Grammy for Best New Artist in 2018 |
| 47% | LYNNE | 5 | Shelby who won the Grammy for Best New Artist in 2001 |
| 47% | EDDIE | 5 | ___ Murphy, comedian who won the Grammy for Best Comedy Recording in 1984 |
| 45% | STRESSEDOUT | 11 | Song for which Twenty One Pilots won the Grammy for Best Pop Duo/Group Performance in 2017: 2 wds. |
| 45% | HER | 3 | One-named singer who won the Academy Award for Best Original Song in 2021 for "Fight for You" from the film "Judas and the Black Messiah" |
| 45% | MORE | 4 | "Kiss Me ___," song by Doja Cat ft. SZA that won the Grammy Award for the Best Pop Duo/Group Performance in 2022 |
| 44% | TOWN | 4 | "Old ___ Road," song by Lil Nas X featuring Billy Ray Cyrus that won the Grammy Award for Best Pop Duo/Group Performance in 2020 |
| 44% | JON | 3 | ___ Batiste, "We Are" singer who won the Grammy Award for Album of the Year in 2022 |
| 44% | NATALIECOLE | 11 | "Unforgettable" singer who won the Best New Artist Grammy in 1976: 2 wds. |
| 43% | MEGAN | 5 | ___ Thee Stallion, rapper with the hit "Savage" who won the Grammy for Best New Artist in 2021 |
| 43% | TRUTH | 5 | "___ Hurts," song by Lizzo which won the 2020 Grammy for Best Pop Solo Performance |
| 43% | LEANN | 5 | With 33-Across, "Blue" singer who won the Best New Artist Grammy in 1997 |
| 43% | ADELE | 5 | British singer who won the Album of the Year Grammy in 2012 for "21" |
| 43% | LIONELRICHIE | 12 | Singer who won the Oscar in 1986 for Best Original Song, "Say You, Say Me": 2 wds. |
| 43% | DRAKE | 5 | Rapper who won the Grammy Award for Best Rap Song in 2017 for "Hotline Bling" |