| 100% | DEBBYBOONE | 10 | "You Light Up My Life" singer who won the Best New Artist Grammy in 1978: 2 wds. |
| 70% | BETTEMIDLER | 11 | "Wind Beneath My Wings" singer who won the Best New Artist Grammy in 1974: 2 wds. |
| 68% | CARLYSIMON | 10 | "You're So Vain" singer who won the Best New Artist Grammy in 1972: 2 wds. |
| 67% | NATALIECOLE | 11 | "Unforgettable" singer who won the Best New Artist Grammy in 1976: 2 wds. |
| 66% | MARIAHCAREY | 11 | "Vision of Love" singer who won the Best New Artist Grammy in 1991: 2 wds. |
| 65% | TONIBRAXTON | 11 | "Another Sad Love Song" singer who won the Best New Artist Grammy in 1994: 2 wds. |
| 60% | TRACYCHAPMAN | 12 | "Fast Car" singer who won the Grammy for Best New Artist in 1989: 2 wds. |
| 59% | CYNDILAUPER | 11 | "Girls Just Wanna Have Fun" singer who won the Grammy for Best New Artist in 1985: 2 wds. |
| 58% | OLIVIARODRIGO | 13 | "Drivers License" singer who won a Best New Artist Grammy in 2022: 2 wds. |
| 57% | AMYWINEHOUSE | 12 | "Rehab" singer who won the Best New Artist and Record of the Year Grammys in 2008: 2 wds. |
| 57% | SHERYLCROW | 10 | "All I Wanna Do" singer who won the Best New Artist and Record of the Year Grammys in 1995: 2 wds. |
| 57% | NORAHJONES | 10 | "Don't Know Why" singer who won the Best New Artist and Record of the Year Grammys in 2003: 2 wds. |
| 56% | MEGHANTRAINOR | 13 | "All About That Bass" singer who won a Best New Artist Grammy in 2016: 2 wds. |
| 56% | LEANN | 5 | With 33-Across, "Blue" singer who won the Best New Artist Grammy in 1997 |
| 55% | SADE | 4 | "The Sweetest Taboo" singer who won the Best New Artist Grammy in 1986 |
| 50% | LIONELRICHIE | 12 | Singer who won the Oscar in 1986 for Best Original Song, "Say You, Say Me": 2 wds. |
| 50% | MORGANWALLEN | 12 | 15-Across, 38-Across, and "7 Summers" singer who won the iHeartRadio Music Awards Best New Country Artist in 2020 (2 wds.) |
| 49% | BILLIEEILISH | 12 | "Bad Guy" singer who won a record five Grammy Awards in 2020, including Best New Artist (2 wds.) |
| 49% | WIZKHALIFA | 10 | "See You Again" rapper who won the BET Award for Best New Artist in 2011: 2 wds. |
| 49% | OLIVIA | 6 | ___ Rodrigo, "Drivers License" singer who won the Grammy Award for Best New Artist in 2022 |
| 49% | VICTORIAMONET | 13 | "Jaguar II" singer who won Best R&B album and Best New Artist at the 2024 Grammy Awards (2 wds.) |
| 49% | VICTORIAMONET | 13 | "On My Mama" R&B singer who won Best New Artist at the 2024 Grammys: 2 wds. |
| 48% | ELVISCOSTELLO | 13 | "Look Now" singer who won the Best Traditional Pop Vocal Album Grammy Award in 2020 (2 wds.) |
| 47% | BRETTELDREDGE | 13 | "Lose My Mind" singer who won the 2014 CMA New Artist of the Year award: 2 wds. |
| 46% | RODDYRICCH | 10 | "The Box" rapper who won the BET Award for Best New Artist in 2020: 2 wds. |
| 46% | MARENMORRIS | 11 | "My Church" singer who won the 2016 CMA New Artist of the Year award: 2 wds. |
| 46% | AMYWINEHOUSE | 12 | British singer who won five Grammys in 2008, including Best New Artist, and died of alcohol poisoning in 2011: 2 wds. |
| 45% | MENATWORK | 9 | Australian pop group who received the Best New Artist Grammy in 1983: 3 wds. |
| 44% | WILLIENELSON | 12 | "Always on My Mind" singer who won one of the first Grammy Legend Awards, in 1990: 2 wds. |
| 44% | JENNIFERHUDSON | 14 | Singer who won the Oscar for Best Performance in a Supporting Role for "Dreamgirls": 2 wds. |