| 100% | THEWEEKND | 9 | Canadian singer with an oddly spelled stage name who was the Top R&B Male Artist at the 2019 Billboard Music Awards (2 wds.) |
| 42% | DOJACAT | 7 | 13-Across, 19-Across, and 38-Across singer who was named New Artist of the Year at the 2020 American Music Awards (2 wds.) |
| 41% | DOJACAT | 7 | Top Female R&B artist at the 2021 Billboard Music Awards: 2 wds. |
| 40% | KALIUCHIS | 9 | 15-Across and 32-Across singer-songwriter who was honored as the Top Latin Female Artist at the 2022 Billboard Music Awards (2 wds.) |
| 40% | THEWEEKND | 9 | Singer with an oddly spelled name whose "Starboy" won Best Urban Contemporary Album at the 2018 Grammy Awards (2 wds.) |
| 35% | THOMASRHETT | 11 | 17-Across and 28-Across singer who was the 2019 Academy of Country Music's Male Artist of the Year (2 wds.) |
| 35% | GOODAS | 6 | "___ Hell," song by Lizzo which was nominated for the 2020 Billboard Music Award for Top R&B Song: 2 wds. |
| 35% | BILLIEEILISH | 12 | "Bad Guy," 17-Across, and 42-Across singer who won Best New Artist at the 2019 MTV Video Music Awards (2 wds.) |
| 34% | CHARLEYPRIDE | 12 | "Kiss an Angel Good Mornin'" singer who was honored with the 1972 Grammy Award for Best Male Country Vocal Performance (2 wds.) |
| 34% | AUSTINMAHONE | 12 | YouTube sensation who was the Artist to Watch at the 2013 MTV Video Music Awards: 2 wds. |
| 33% | HARRYSTYLES | 11 | "As It Was" singer who was honored with the People's Choice Award for The Male Artist of 2022 (2 wds.) |
| 33% | TAYLORSWIFT | 11 | "Love Story" singer-songwriter who won the award for Top Female Artist in Billboard 2018: 2 wds. |
| 33% | DRAKE | 5 | Singer of 15-Across, 28-Across, and 38-Across who was honored with the Artist of the Decade Award at the 2021 "Billboard" Music Awards |
| 32% | JUSTINBIEBER | 12 | "Love Yourself" pop singer who was Billboard's Top Male Artist of 2016: 2 wds. |
| 32% | CYNDILAUPER | 11 | "Time After Time" singer who was honored with the "Billboard" Women in Music Icon Award in 2018 (2 wds.) |
| 32% | YOLANDAADAMS | 12 | "Be Blessed" gospel singer who was honored with the 2019 Soul Train Lady of Soul Award: 2 wds. |
| 32% | JANELLEMONAE | 12 | "Dirty Computer" singer who won the GLAAD Media Award for Outstanding Music Artist in 2019: 2 wds. |
| 32% | CHARLEYPRIDE | 12 | "Kiss an Angel Good Mornin'" singer who was the first Black country artist to cohost the CMA Awards (1975) and the ACM Awards (1980): 2 wds. |
| 32% | VICTORIAMONET | 13 | "Jaguar II" singer who won Best R&B album and Best New Artist at the 2024 Grammy Awards (2 wds.) |
| 32% | EDSHEERAN | 9 | "Shape Of You" artist who won the award for the Top Male Artist in Billboard 2018: 2 wds. |
| 32% | BRUNOMARS | 9 | "Please Me" collaborator who won the 2019 BET Award for Best Male R&B/Pop Artist (2 wds.) |
| 32% | HARRYSTYLES | 11 | "As It Was" singer who won the People's Choice Award for Male Artist of 2022: 2 wds. |
| 32% | JENNIFERLOPEZ | 13 | "If You Had My Love" singer who was honored with the "Billboard" Women in Music Icon Award in 2020 (2 wds.) |
| 32% | BRETTELDREDGE | 13 | "Somethin' I'm Good At" singer who topped the Billboard Country Albums chart with his latest LP: 2 wds. |
| 31% | LUKECOMBS | 9 | 15-Across and 33-Across singer who won the 2019 Country Music Association's New Artist of the Year Award (2 wds.) |
| 31% | SHANIATWAIN | 11 | "That Don't Impress Me Much" singer who was honored with the "Billboard" Women in Music Icon Award in 2016 (2 wds.) |
| 31% | BADBUNNY | 8 | "Dákiti" singer who won five Billboard Music Awards, including Top Latin Artist, in 2021 (2 wds.) |
| 31% | TAYLORSWIFT | 11 | "Anti-Hero" singer who is nominated for a 2022 American Music Award for Artist of the Year (2 wds.) |
| 31% | THEWEEKND | 9 | "Blinding Lights" singer who won Video of the Year and Best R&B at the 2020 MTV Video Music Awards (2 wds.) |
| 31% | HARRYSTYLES | 11 | "As It Was" singer who is nominated for a 2022 American Music Award for Artist of the Year (2 wds.) |