| 100% | POPSMOKE | 8 | "What You Know Bout Love" singer who won five Billboard Music Awards, including Top New Artist, in 2021 (2 wds.) |
| 71% | BADBUNNY | 8 | "Dákiti" singer who won five Billboard Music Awards, including Top Latin Artist, in 2021 (2 wds.) |
| 60% | GABBYBARRETT | 12 | "I Hope" singer who won three Billboard Music Awards, including Top Country Female Artist, in 2021 (2 wds.) |
| 49% | BILLIEEILISH | 12 | "Bad Guy" singer who won a record five Grammy Awards in 2020, including Best New Artist (2 wds.) |
| 47% | AMYWINEHOUSE | 12 | British singer who won five Grammys in 2008, including Best New Artist, and died of alcohol poisoning in 2011: 2 wds. |
| 45% | SAMSMITH | 8 | "Love Goes" singer who won the GLAAD Media Award for Outstanding Music Artist in 2021: 2 wds. |
| 44% | TAYLORSWIFT | 11 | "Love Story" singer-songwriter who won the award for Top Female Artist in Billboard 2018: 2 wds. |
| 43% | JENNIFERLOPEZ | 13 | "If You Had My Love" singer who received the Billboard Women in Music Icon Award in 2020: 2 wds. |
| 41% | 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 the award for R&B Song, "That's What I Like" in Billboard 2018: 2 wds |
| 40% | TAYLORSWIFT | 11 | "You Need to Calm Down" singer who won six 2019 American Music Awards, including Artist of the Decade (2 wds.) |
| 40% | ZAYN | 4 | "Pillowtalk" singer who won the Billboard Music Award for New Artist of the Year as a member of One Direction in 2013 and as a solo artist in 2017 |
| 40% | JUSTINBIEBER | 12 | 26-time "Billboard" Music Award winner who had five Top 10 hits in 2020, including 17-Across and 39-Across (2 wds.) |
| 40% | ALISONKRAUSS | 12 | "Raising Sand" singer who won five Grammy Awards in 2009: 2 wds. |
| 39% | CARLYSIMON | 10 | "You're So Vain" singer who won the Best New Artist Grammy in 1972: 2 wds. |
| 39% | AMYWINEHOUSE | 12 | "Back to Black" singer who won five Grammy Awards in 2008: 2 wds. |
| 39% | JANELLEMONAE | 12 | "Dirty Computer" singer who won the GLAAD Media Award for Outstanding Music Artist in 2019: 2 wds. |
| 39% | LAINEYWILSON | 12 | "Heart Like a Truck" singer who won five awards, including Entertainer of the Year, at the 2023 Country Music Association Awards (2 wds.) |
| 39% | EDSHEERAN | 9 | "Shape Of You" artist who won the award for the Top Male Artist in Billboard 2018: 2 wds. |
| 39% | TAYLORSWIFT | 11 | "Look What You Made Me Do" singer who has won the most Billboard Music Awards (23) (2 wds.) |
| 39% | TONIBRAXTON | 11 | "Another Sad Love Song" singer who won the Best New Artist Grammy in 1994: 2 wds. |
| 38% | NORAHJONES | 10 | "Don't Know Why" singer who won the Best New Artist and Record of the Year Grammys in 2003: 2 wds. |
| 38% | JENNIFERLOPEZ | 13 | "If You Had My Love" singer who was honored with the "Billboard" Women in Music Icon Award in 2020 (2 wds.) |
| 38% | LADYGAGA | 8 | "Born This Way" singer who won the GLAAD Media Award for Outstanding Music Artist in 2012: 2 wds. |
| 38% | NATALIECOLE | 11 | "Unforgettable" singer who won the Best New Artist Grammy in 1976: 2 wds. |
| 38% | BILLIEEILISH | 12 | "Bad Guy," 17-Across, and 42-Across singer who won Best New Artist at the 2019 MTV Video Music Awards (2 wds.) |
| 38% | LUKECOMBS | 9 | 15-Across and 33-Across singer who won the 2019 Country Music Association's New Artist of the Year Award (2 wds.) |
| 38% | DEBBYBOONE | 10 | "You Light Up My Life" singer who won the Best New Artist Grammy in 1978: 2 wds. |
| 38% | OLIVIARODRIGO | 13 | "Drivers License" singer who won a Best New Artist Grammy in 2022: 2 wds. |
| 38% | BILLIEEILISH | 12 | "All the Good Girls Go to Hell" singer who won the 2019 American Music Award for New Artist of the Year (2 wds.) |