| 100% | THEWEEKND | 9 | 16-Across and 34-Across singer who won the 2018 Best Urban Contemporary Album Grammy for "Starboy" (2 wds.) |
| 60% | THEWEEKND | 9 | Singer with an oddly spelled name whose "Starboy" won Best Urban Contemporary Album at the 2018 Grammy Awards (2 wds.) |
| 55% | RIHANNA | 7 | One-named singer who won the Grammy Award for Best Urban Contemporary Album for "Unapologetic" in 2014 |
| 54% | KACEYMUSGRAVES | 14 | 19-Across and 46-Across singer who won four 2019 Grammys, including Album of the Year and Best Country Album for "Golden Hour" (2 wds.) |
| 52% | PEABOBRYSON | 11 | Singer/songwriter who won Grammy Awards for 34-Across and the "Beauty and the Beast" theme (2 wds.) |
| 51% | PHOEBEBRIDGERS | 14 | 16-Across and 31-Across singer who was nominated for a 2020 Best New Artist Grammy Award (2 wds.) |
| 51% | TRACYCHAPMAN | 12 | "Fast Car" singer who won the Grammy for Best New Artist in 1989: 2 wds. |
| 51% | MIRANDALAMBERT | 14 | Singer whose "Wildcard" won the Grammy for Best Country Album in 2021: 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% | CHRISSTAPLETON | 14 | Singer whose "Starting Over" won the Grammy for Best Country Album in 2022: 2 wds. |
| 50% | CYNDILAUPER | 11 | "Girls Just Wanna Have Fun" singer who won the Grammy for Best New Artist in 1985: 2 wds. |
| 50% | VICTORIAMONET | 13 | "Jaguar II" singer who won Best R&B album and Best New Artist at the 2024 Grammy Awards (2 wds.) |
| 50% | EDSHEERAN | 9 | "Shape of You" singer who won two awards, including Best Pop Vocal Album, at the 2018 Grammy Awards (2 wds.) |
| 49% | KATHYGRIFFIN | 12 | "My Life on the D-List" star who won a Grammy for Best Comedy Album in 2014: 2 wds. |
| 49% | ELVISCOSTELLO | 13 | "Look Now" singer who won the Best Traditional Pop Vocal Album Grammy Award in 2020 (2 wds.) |
| 49% | ALISONKRAUSS | 12 | Singer who won her 27th Grammy for the 2011 bluegrass album "Paper Airplane": 2 wds. |
| 49% | BRANDICARLILE | 13 | 18-Across and 42-Across singer who won a Best Country Song Grammy Award for "Bring My Flowers Now" (2 wds.) |
| 48% | CELINEDION | 10 | Singer whose 1996 album "Falling into You" won Grammy Awards for Album of the Year and Best Pop Album (2 wds.) |
| 48% | KATRINALENK | 11 | 30-Across singer/actress who won the 2018 Tony Award for Best Actress in a Musical (2 wds.) |
| 48% | KELLYCLARKSON | 13 | 16-Across and 45-Across singer who won the first season of "American Idol" (2 wds.) |
| 47% | MEGHANTRAINOR | 13 | "All About the Bass" And "Lips Are Movin" singer who won the 2016 Best New Artist Grammy Award (2 wds.) |
| 47% | TIFFANYHADDISH | 14 | "The Last O.G." actress who won a Grammy for Best Comedy Album in 2021: 2 wds. |
| 47% | LAINEYWILSON | 12 | "Bell Bottom Country" singer who won Best Country Album at the 2024 Grammy Awards (2 wds.) |
| 47% | BILLIEEILISH | 12 | "Bad Guy" singer who received the Grammys for both Album of the Year and Best New Artist in 2020: 2 wds. |
| 46% | LAURYNHILL | 10 | "Everything Is Everything" singer who received the Grammys for both Album of the Year and Best New Artist in 1999: 2 wds. |
| 46% | NORAHJONES | 10 | "Come Away With Me" singer who received the Grammys for both Album of the Year and Best New Artist in 2003: 2 wds. |
| 45% | MARENMORRIS | 11 | "Girl" singer who won the 2019 CMA Award for Album of the Year (2 wds.) |
| 45% | NATALIECOLE | 11 | "Unforgettable" singer who won the Best New Artist Grammy in 1976: 2 wds. |
| 45% | DAVIDBOWIE | 10 | Glam rock legend who won a posthumous Best Alternative Music Album Grammy in 2017 for "Blackstar": 2 wds. |
| 45% | JENNIFERHUDSON | 14 | Singer who won the Oscar for Best Performance in a Supporting Role for "Dreamgirls": 2 wds. |