| 100% | WILLIENELSON | 12 | "Always on My Mind" singer who won one of the first Grammy Legend Awards, in 1990: 2 wds. |
| 81% | SMOKEYROBINSON | 14 | "I Second That Emotion" singer who won one of the first Grammy Legend Awards, in 1990: 2 wds. |
| 81% | LIZAMINNELLI | 12 | "Cabaret" star and singer who won one of the first Grammy Legend Awards, in 1990: 2 wds. |
| 49% | BRETTELDREDGE | 13 | "Lose My Mind" singer who won the 2014 CMA New Artist of the Year award: 2 wds. |
| 46% | MILEYCYRUS | 10 | Singer who won Video of the Year for "Wrecking Ball" at MTV Video Music Awards in 2014: 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. |
| 45% | RAYCHARLES | 10 | "Georgia on My Mind" singer who was a charter inductee into the Rock and Roll Hall of Fame: 2 wds. |
| 45% | SHAWNMENDES | 11 | "Señorita" singer who won Canada's Juno Award for Pop Album of the Year in 2019: 2 wds. |
| 44% | MIRANDALAMBERT | 14 | "Vice" singer who came in third on the first season of "Nashville Star": 2 wds. |
| 43% | ARTHURASHKIN | 12 | American scientist who won one half of the 2018 Nobel Prize in Physics for his work on optical tweezers: 2 wds. |
| 42% | MARENMORRIS | 11 | "My Church" singer who won the 2016 CMA New Artist of the Year award: 2 wds. |
| 42% | SAMSMITH | 8 | "Stay With Me" singer who was a first-time Grammy nominee for Record of the Year (and won): 2 wds. |
| 42% | BETTEMIDLER | 11 | "Wind Beneath My Wings" singer who won the Best New Artist Grammy in 1974: 2 wds. |
| 42% | MARIAHCAREY | 11 | "Vision of Love" singer who won the Best New Artist Grammy in 1991: 2 wds. |
| 41% | BRUNOMARS | 9 | "24K Magic" singer who won six awards, including Record of the Year, at the 2018 Grammy Awards (2 wds.) |
| 41% | DEBBYBOONE | 10 | "You Light Up My Life" singer who won the Best New Artist Grammy in 1978: 2 wds. |
| 41% | WILLIENELSON | 12 | "Always on My Mind" country singer recognized by the Kennedy Center Honors in 1998 (2 wds.) |
| 40% | NATALIECOLE | 11 | "Unforgettable" singer who won the Best New Artist Grammy in 1976: 2 wds. |
| 40% | EILISH | 6 | Billie ___, singer who won five Grammy awards including Record of the Year in 2020 |
| 40% | TRACYCHAPMAN | 12 | "Fast Car" singer who won the Grammy for Best New Artist in 1989: 2 wds. |
| 40% | ALESSIACARA | 11 | "Stay" singer who won the Pop Album of the Year Juno in 2017: 2 wds. |
| 40% | RAYCHARLES | 10 | "Georgia on My Mind" singer who went by his first and middle names, not his last name (Robinson): 2 wds. |
| 40% | CYNDILAUPER | 11 | "Girls Just Wanna Have Fun" singer who won the Grammy for Best New Artist in 1985: 2 wds. |
| 40% | AMYWINEHOUSE | 12 | "Rehab" singer who won the Best New Artist and Record of the Year Grammys in 2008: 2 wds. |
| 40% | LADYGAGA | 8 | "Born This Way" singer who won the GLAAD Media Award for Outstanding Music Artist in 2012: 2 wds. |
| 40% | HARRYSTYLES | 11 | "As It Was" singer who won the People's Choice Award for Male Artist of 2022: 2 wds. |
| 40% | JON | 3 | ___ Batiste, "We Are" singer who won the Grammy Award for Album of the Year in 2022 |
| 40% | CARLYSIMON | 10 | "You're So Vain" singer who won the Best New Artist Grammy in 1972: 2 wds. |
| 40% | TONIBRAXTON | 11 | "Another Sad Love Song" singer who won the Best New Artist Grammy in 1994: 2 wds. |
| 39% | SOLANGEKNOWLES | 14 | 12-Across and 28-Across singer who was the first recipient of the "Billboard" Women in Music Impact Award (2 wds.) |