| 100% | GABBYBARRETT | 12 | "I Hope" singer who won three Billboard Music Awards, including Top Country Female Artist, in 2021 (2 wds.) |
| 67% | BADBUNNY | 8 | "Dákiti" singer who won five Billboard Music Awards, including Top Latin Artist, in 2021 (2 wds.) |
| 64% | POPSMOKE | 8 | "What You Know Bout Love" singer who won five Billboard Music Awards, including Top New Artist, in 2021 (2 wds.) |
| 50% | CARLYPEARCE | 11 | "I Hope You're Happy Now" singer/songwriter who won the 2021 Country Music Association Award for Female Vocalist of the Year (2 wds.) |
| 48% | TAYLORSWIFT | 11 | "Love Story" singer-songwriter who won the award for Top Female Artist in Billboard 2018: 2 wds. |
| 47% | SAMSMITH | 8 | "Love Goes" singer who won the GLAAD Media Award for Outstanding Music Artist in 2021: 2 wds. |
| 46% | BRITNEYSPEARS | 13 | Singer who won Video of the Year for "Piece of Me" at MTV Video Music Awards in 2008: 2 wds. |
| 45% | MIRANDALAMBERT | 14 | "Tin Man" singer who won Female Vocalist of the Year at the 2018 Academy of Country Music Awards: 2 wds. |
| 45% | BRUNOMARS | 9 | "24K Magic" singer who won the award for R&B Song, "That's What I Like" in Billboard 2018: 2 wds |
| 45% | TAYLORSWIFT | 11 | "Lover" singer who won three 2019 MTV Video Music Awards, including Video of the Year (2 wds.) |
| 44% | BILLIEEILISH | 12 | "Bad Guy" singer who won a record five Grammy Awards in 2020, including Best New Artist (2 wds.) |
| 43% | JANELLEMONAE | 12 | "Dirty Computer" singer who won the GLAAD Media Award for Outstanding Music Artist in 2019: 2 wds. |
| 43% | LADYGAGA | 8 | "Born This Way" singer who won the GLAAD Media Award for Outstanding Music Artist in 2012: 2 wds. |
| 43% | TAYLORSWIFT | 11 | "You Need to Calm Down" singer who won six 2019 American Music Awards, including Artist of the Decade (2 wds.) |
| 42% | DOJACAT | 7 | Top Female R&B artist at the 2021 Billboard Music Awards: 2 wds. |
| 42% | LUKECOMBS | 9 | 15-Across and 33-Across singer who won the 2019 Country Music Association's New Artist of the Year Award (2 wds.) |
| 42% | 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.) |
| 42% | EDSHEERAN | 9 | "Shape Of You" artist who won the award for the Top Male Artist in Billboard 2018: 2 wds. |
| 41% | MORGANWALLEN | 12 | 15-Across, 38-Across, and "7 Summers" singer who won the iHeartRadio Music Awards Best New Country Artist in 2020 (2 wds.) |
| 41% | MILEYCYRUS | 10 | Singer who won Video of the Year for "Wrecking Ball" at MTV Video Music Awards in 2014: 2 wds. |
| 40% | REBAMCENTIRE | 12 | Country Music Hall of Fame singer who's won the American Music Award for Favorite Female Country Artist a record 11 times (2 wds.) |
| 40% | SHANIATWAIN | 11 | "That Don't Impress Me Much" singer who received the Billboard Women in Music Icon Award in 2016: 2 wds. |
| 40% | AMYWINEHOUSE | 12 | British singer who won five Grammys in 2008, including Best New Artist, and died of alcohol poisoning in 2011: 2 wds. |
| 40% | JASONALDEAN | 11 | "You Make It Easy" singer who won Entertainer of the Year at the 2018 Academy of Country Music Awards: 2 wds. |
| 40% | THOMASRHETT | 11 | "Country Again" singer who won Entertainer of the Year at the 2020 Academy of Country Music Awards: 2 wds. |
| 40% | BONNIERAITT | 11 | "Something to Talk About" singer who received the Billboard Women in Music Icon Award in 2021: 2 wds. |
| 39% | PETERGABRIEL | 12 | "Big Time" singer who won 10 MTV Video Music Awards in 1987, the most wins ever in a single night: 2 wds. |
| 39% | 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 |
| 39% | IGGYAZALEA | 10 | "Fancy" rapper who won the American Music Award for Favorite Rap/Hip-Hop Artist in 2014: 2 wds. |
| 39% | JUSTINBIEBER | 12 | 26-time "Billboard" Music Award winner who had five Top 10 hits in 2020, including 17-Across and 39-Across (2 wds.) |