| 100% | THEWEEKND | 9 | Singer with an oddly spelled name whose "Starboy" won Best Urban Contemporary Album at the 2018 Grammy Awards (2 wds.) |
| 50% | AIMEEMANN | 9 | Former 'Til Tuesday lead singer whose "Mental Illness" won Best Folk Album at the 2018 Grammy Awards (2 wds.) |
| 49% | THEWEEKND | 9 | Canadian singer with an oddly spelled stage name who was the Top R&B Male Artist at the 2019 Billboard Music Awards (2 wds.) |
| 46% | LOEB | 4 | Singer Lisa whose "Feel What U Feel" won Best Children's Album at the 2018 Grammy Awards |
| 45% | EDSHEERAN | 9 | "Shape of You" singer who won two awards, including Best Pop Vocal Album, at the 2018 Grammy Awards (2 wds.) |
| 44% | THEWEEKND | 9 | 16-Across and 34-Across singer who won the 2018 Best Urban Contemporary Album Grammy for "Starboy" (2 wds.) |
| 42% | LAINEYWILSON | 12 | "Bell Bottom Country" singer who won Best Country Album at the 2024 Grammy Awards (2 wds.) |
| 39% | SHAKIRA | 7 | One-named singer whose album "El Dorado" won the 2018 Grammy Award for Best Latin Pop Album |
| 38% | RIHANNA | 7 | One-named singer who won the Grammy Award for Best Urban Contemporary Album for "Unapologetic" in 2014 |
| 37% | BILLIEEILISH | 12 | Grammy Award-winning singer with the new album "Happier Than Ever" (2 wds.) |
| 37% | VICTORIAMONET | 13 | "Jaguar II" singer who won Best R&B album and Best New Artist at the 2024 Grammy Awards (2 wds.) |
| 36% | CELINEDION | 10 | Singer whose 1996 album "Falling into You" won Grammy Awards for Album of the Year and Best Pop Album (2 wds.) |
| 36% | MIRANDALAMBERT | 14 | Singer whose "Wildcard" won the Grammy for Best Country Album in 2021: 2 wds. |
| 36% | CARA | 4 | Singer Alessia who won Best New Artist at the 2018 Grammy Awards |
| 36% | TRUTHHURTS | 10 | 1-Across hit that won Best Pop Solo Performance at the 2020 Grammy Awards: 2 wds. |
| 35% | WILLIE | 6 | With 39-Across, singer whose "A Beautiful Time" won the Grammy for Best Country Album in 2023 |
| 34% | FOOFIGHTERS | 11 | Band whose "Run" won the 2018 Grammy for Best Rock Song: 2 wds. |
| 34% | TAYLORSWIFT | 11 | Singer-songwriter whose "1989" won 2016's Grammy Award for Album of the Year (2 wds.) |
| 34% | MORNINGPHASE | 12 | Beck album that won the 2015 Grammy Award for Best Rock Album: 2 wds. |
| 34% | THERESISTANCE | 13 | Muse album that won the 2011 Grammy Award for Best Rock Album: 2 wds. |
| 34% | BRUNOMARS | 9 | "24K Magic" singer who won six awards, including Record of the Year, at the 2018 Grammy Awards (2 wds.) |
| 33% | WASTINGLIGHT | 12 | Foo Fighters album that won the 2012 Grammy Award for Best Rock Album: 2 wds. |
| 33% | CHANNELORANGE | 13 | Frank Ocean's 2013 Grammy-winning Best Urban Contemporary Album: 2 wds. |
| 33% | ANDREABOCELLI | 13 | Italian classical singer whose album "Cinema" was nominated for Best Traditional Pop Vocal Album in the 2017 Grammy Awards : 2 wds. |
| 32% | CHRISSTAPLETON | 14 | Singer whose "Starting Over" won the Grammy for Best Country Album in 2022: 2 wds. |
| 31% | ANNAMAZZOLA | 11 | Author whose novel "The Unseeing" won the 2018 Edgar Award in the Best Paperback Original category: 2 wds. |
| 31% | ALLISONJANNEY | 13 | Best Supporting Actress winner at the 2018 Critics' Choice Awards for her role in "I, Tonya": 2 wds. |
| 31% | THEWARONDRUGS | 13 | Band which won the Grammy for Best Rock Album in 2018: 4 wds. |
| 30% | JOHNCROWLEY | 11 | Author whose short story "Spring Break" won the 2018 Edgar Award in the Best Short Story category: 2 wds. |
| 30% | JASONREYNOLDS | 13 | Author whose novel "Long Way Down" won the 2018 Edgar Award in the Best Young Adult category: 2 wds. |