| 100% | GLORIAGAYNOR | 12 | 43-Across singer who won the only 19-Across/36-Across Grammy Award (2 wds.) |
| 61% | LAINEYWILSON | 12 | "Bell Bottom Country" singer who won Best Country Album at the 2024 Grammy Awards (2 wds.) |
| 59% | ELVISCOSTELLO | 13 | "Look Now" singer who won the Best Traditional Pop Vocal Album Grammy Award in 2020 (2 wds.) |
| 57% | LIZAMINNELLI | 12 | "Cabaret" star and singer who won one of the first Grammy Legend Awards, in 1990: 2 wds. |
| 57% | SMOKEYROBINSON | 14 | "I Second That Emotion" singer who won one of the first Grammy Legend Awards, in 1990: 2 wds. |
| 57% | WILLIENELSON | 12 | "Always on My Mind" singer who won one of the first Grammy Legend Awards, in 1990: 2 wds. |
| 56% | PEABOBRYSON | 11 | Singer/songwriter who won Grammy Awards for 34-Across and the "Beauty and the Beast" theme (2 wds.) |
| 55% | MARIAHCAREY | 11 | "Vision of Love" singer who won the Best New Artist Grammy in 1991: 2 wds. |
| 55% | NATALIECOLE | 11 | "Unforgettable" singer who won the Best New Artist Grammy in 1976: 2 wds. |
| 55% | TRACYCHAPMAN | 12 | "Fast Car" singer who won the Grammy for Best New Artist in 1989: 2 wds. |
| 54% | MEGHANTRAINOR | 13 | "All About the Bass" And "Lips Are Movin" singer who won the 2016 Best New Artist Grammy Award (2 wds.) |
| 54% | BETTEMIDLER | 11 | "Wind Beneath My Wings" singer who won the Best New Artist Grammy in 1974: 2 wds. |
| 54% | CARLYSIMON | 10 | "You're So Vain" singer who won the Best New Artist Grammy in 1972: 2 wds. |
| 54% | TONIBRAXTON | 11 | "Another Sad Love Song" singer who won the Best New Artist Grammy in 1994: 2 wds. |
| 54% | THEWEEKND | 9 | 16-Across and 34-Across singer who won the 2018 Best Urban Contemporary Album Grammy for "Starboy" (2 wds.) |
| 54% | DEBBYBOONE | 10 | "You Light Up My Life" singer who won the Best New Artist Grammy in 1978: 2 wds. |
| 53% | CYNDILAUPER | 11 | "Girls Just Wanna Have Fun" singer who won the Grammy for Best New Artist in 1985: 2 wds. |
| 53% | LAURIEANDERSON | 14 | "O Superman" singer who received the Grammy Lifetime Achievement Award in 2024: 2 wds. |
| 53% | BRUNOMARS | 9 | "24K Magic" singer who won six awards, including Record of the Year, at the 2018 Grammy Awards (2 wds.) |
| 53% | GARTHBROOKS | 11 | "The Dance" singer who won the 2016 CMA Award for Entertainer of the Year: 2 wds. |
| 53% | ALISONKRAUSS | 12 | Singer who won her 27th Grammy for the 2011 bluegrass album "Paper Airplane": 2 wds. |
| 53% | EDSHEERAN | 9 | "Shape of You" singer who won two awards, including Best Pop Vocal Album, at the 2018 Grammy Awards (2 wds.) |
| 53% | VICTORIAMONET | 13 | "Jaguar II" singer who won Best R&B album and Best New Artist at the 2024 Grammy Awards (2 wds.) |
| 52% | LAMELOBALL | 10 | 2021 NBA Rookie of the Year who won the 2021 Best Breakthrough Athlete 36-Across Award (2 wds.) |
| 52% | GARTHBROOKS | 11 | "The River" singer who won the CMA Award for Entertainer of the Year seven times: 2 wds. |
| 52% | MARENMORRIS | 11 | "My Church" singer who won the 2016 CMA New Artist of the Year award: 2 wds. |
| 52% | GLADYSKNIGHT | 12 | "Midnight Train to Georgia" singer who received the Grammy Lifetime Achievement Award in 2024: 2 wds. |
| 52% | TAMMYWYNETTE | 12 | "Stand by Your Man" singer who received the Grammy Lifetime Achievement Award in 2024: 2 wds. |
| 52% | LEANNRIMES | 10 | Singer who is the youngest ever individual artist to win the Grammy: 2 wds. |
| 52% | ALISONKRAUSS | 12 | "Raising Sand" singer who won five Grammy Awards in 2009: 2 wds. |