| 100% | EDSHEERAN | 9 | "Shape of You" singer who won two awards, including Best Pop Vocal Album, at the 2018 Grammy Awards (2 wds.) |
| 63% | BRUNOMARS | 9 | "24K Magic" singer who won six awards, including Record of the Year, at the 2018 Grammy Awards (2 wds.) |
| 59% | THEWEEKND | 9 | Singer with an oddly spelled name whose "Starboy" won Best Urban Contemporary Album at the 2018 Grammy Awards (2 wds.) |
| 57% | AIMEEMANN | 9 | Former 'Til Tuesday lead singer whose "Mental Illness" won Best Folk Album at the 2018 Grammy Awards (2 wds.) |
| 57% | ELVISCOSTELLO | 13 | "Look Now" singer who won the Best Traditional Pop Vocal Album Grammy Award in 2020 (2 wds.) |
| 55% | CELINEDION | 10 | Singer whose 1996 album "Falling into You" won Grammy Awards for Album of the Year and Best Pop Album (2 wds.) |
| 54% | JASONALDEAN | 11 | "You Make It Easy" singer who won Entertainer of the Year at the 2018 Academy of Country Music Awards: 2 wds. |
| 53% | ANDREABOCELLI | 13 | Italian classical singer whose album "Cinema" was nominated for Best Traditional Pop Vocal Album in the 2017 Grammy Awards : 2 wds. |
| 53% | SHAWNMENDES | 11 | "Señorita" singer who won Canada's Juno Award for Pop Album of the Year in 2019: 2 wds. |
| 52% | LAINEYWILSON | 12 | "Bell Bottom Country" singer who won Best Country Album at the 2024 Grammy Awards (2 wds.) |
| 52% | VICTORIAMONET | 13 | "Jaguar II" singer who won Best R&B album and Best New Artist at the 2024 Grammy Awards (2 wds.) |
| 52% | JASONALDEAN | 11 | "Burnin' It Down" singer who won Entertainer of the Year at the 2016, 2017, and 2018 ACM Awards: 2 wds. |
| 50% | EDSHEERAN | 9 | "Shape Of You" artist who won the award for the Top Male Artist in Billboard 2018: 2 wds. |
| 50% | LOEB | 4 | Singer Lisa whose "Feel What U Feel" won Best Children's Album at the 2018 Grammy Awards |
| 50% | TRUTHHURTS | 10 | 1-Across hit that won Best Pop Solo Performance at the 2020 Grammy Awards: 2 wds. |
| 50% | SHEERAN | 7 | Ed who won the Grammy for Best Pop Vocal Album in 2018 |
| 49% | MIRANDALAMBERT | 14 | "Tin Man" singer who won Female Vocalist of the Year at the 2018 Academy of Country Music Awards: 2 wds. |
| 48% | LAINEYWILSON | 12 | "Heart Like a Truck" singer who won five awards, including Entertainer of the Year, at the 2023 Country Music Association Awards (2 wds.) |
| 47% | FIONAAPPLE | 10 | Art pop singer-songwriter who won a Best Alternative Music Album Grammy in 2021 for "Fetch the Bolt Cutters": 2 wds. |
| 46% | THEWEEKND | 9 | 16-Across and 34-Across singer who won the 2018 Best Urban Contemporary Album Grammy for "Starboy" (2 wds.) |
| 46% | THOMASRHETT | 11 | "Country Again" singer who won Entertainer of the Year at the 2020 Academy of Country Music Awards: 2 wds. |
| 46% | MILEYCYRUS | 10 | Singer who won Video of the Year for "Wrecking Ball" at MTV Video Music Awards in 2014: 2 wds. |
| 46% | SHAKIRA | 7 | One-named singer whose album "El Dorado" won the 2018 Grammy Award for Best Latin Pop Album |
| 46% | MARIAHCAREY | 11 | "Vision of Love" singer who won the Best New Artist Grammy in 1991: 2 wds. |
| 45% | THEWEEKND | 9 | "Blinding Lights" singer who won Video of the Year and Best R&B at the 2020 MTV Video Music Awards (2 wds.) |
| 45% | CARA | 4 | Singer Alessia who won Best New Artist at the 2018 Grammy Awards |
| 45% | TAYLORSWIFT | 11 | "You Need to Calm Down" singer who won six 2019 American Music Awards, including Artist of the Decade (2 wds.) |
| 45% | ALESSIACARA | 11 | "Stay" singer who won the Pop Album of the Year Juno in 2017: 2 wds. |
| 45% | STEVIEWONDER | 12 | American artist who has won the Grammy thrice for "Best Album of the Year," including one for "Innervisions": 2 wds. |
| 45% | BRITNEYSPEARS | 13 | Singer who won Video of the Year for "Piece of Me" at MTV Video Music Awards in 2008: 2 wds. |