| 100% | BILLIE | 6 | With 34-Across, "Bad Guy" singer who won a Best New Artist Grammy in 2020 |
| 72% | BILLIEEILISH | 12 | "Bad Guy" singer who won a record five Grammy Awards in 2020, including Best New Artist (2 wds.) |
| 66% | OLIVIARODRIGO | 13 | "Drivers License" singer who won a Best New Artist Grammy in 2022: 2 wds. |
| 65% | MEGHANTRAINOR | 13 | "All About That Bass" singer who won a Best New Artist Grammy in 2016: 2 wds. |
| 62% | LEANN | 5 | With 33-Across, "Blue" singer who won the Best New Artist Grammy in 1997 |
| 55% | NATALIECOLE | 11 | "Unforgettable" singer who won the Best New Artist Grammy in 1976: 2 wds. |
| 54% | SADE | 4 | "The Sweetest Taboo" singer who won the Best New Artist Grammy in 1986 |
| 53% | MARIAHCAREY | 11 | "Vision of Love" singer who won the Best New Artist Grammy in 1991: 2 wds. |
| 52% | BETTEMIDLER | 11 | "Wind Beneath My Wings" singer who won the Best New Artist Grammy in 1974: 2 wds. |
| 52% | CARLYSIMON | 10 | "You're So Vain" singer who won the Best New Artist Grammy in 1972: 2 wds. |
| 52% | TONIBRAXTON | 11 | "Another Sad Love Song" singer who won the Best New Artist Grammy in 1994: 2 wds. |
| 51% | DEBBYBOONE | 10 | "You Light Up My Life" singer who won the Best New Artist Grammy in 1978: 2 wds. |
| 50% | ENYA | 4 | Singer who won a Best New Age Album Grammy Award for "Amarantine" |
| 50% | OLIVIA | 6 | ___ Rodrigo, "Drivers License" singer who won the Grammy Award for Best New Artist in 2022 |
| 50% | TRACYCHAPMAN | 12 | "Fast Car" singer who won the Grammy for Best New Artist in 1989: 2 wds. |
| 49% | CYNDILAUPER | 11 | "Girls Just Wanna Have Fun" singer who won the Grammy for Best New Artist in 1985: 2 wds. |
| 47% | MORGANWALLEN | 12 | 15-Across, 38-Across, and "7 Summers" singer who won the iHeartRadio Music Awards Best New Country Artist in 2020 (2 wds.) |
| 46% | BILLIEEILISH | 12 | "Bad Guy" singer who received the Grammys for both Album of the Year and Best New Artist in 2020: 2 wds. |
| 45% | DAVID | 5 | ___ Bowie, English singer who won a Grammy Award for best music video in 1985 |
| 45% | JOHN | 4 | ___ Legend, American singer who won a Grammy for Best R&B Album in 2006 |
| 45% | ADAMS | 5 | Bryan ___, Canadian singer who won a Grammy for Best Song Written for Visual Media in 1992 |
| 44% | AMYWINEHOUSE | 12 | "Rehab" singer who won the Best New Artist and Record of the Year Grammys in 2008: 2 wds. |
| 42% | VICTORIAMONET | 13 | "Jaguar II" singer who won Best R&B album and Best New Artist at the 2024 Grammy Awards (2 wds.) |
| 42% | TAYLORSWIFT | 11 | Singer who was nominated for a Grammy for Best New Artist in 2008 but lost to Amy Winehouse: 2 wds. |
| 41% | CARA | 4 | Singer Alessia who won Best New Artist at the 2018 Grammy Awards |
| 41% | AMYWINEHOUSE | 12 | British singer who won five Grammys in 2008, including Best New Artist, and died of alcohol poisoning in 2011: 2 wds. |
| 41% | PHOEBEBRIDGERS | 14 | 16-Across and 31-Across singer who was nominated for a 2020 Best New Artist Grammy Award (2 wds.) |
| 41% | SHERYLCROW | 10 | "All I Wanna Do" singer who won the Best New Artist and Record of the Year Grammys in 1995: 2 wds. |
| 41% | NORAHJONES | 10 | "Don't Know Why" singer who won the Best New Artist and Record of the Year Grammys in 2003: 2 wds. |
| 41% | ELVISCOSTELLO | 13 | "Look Now" singer who won the Best Traditional Pop Vocal Album Grammy Award in 2020 (2 wds.) |