| 100% | 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.) |
| 53% | 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 |
| 49% | DOJACAT | 7 | Top Female R&B artist at the 2021 Billboard Music Awards: 2 wds. |
| 49% | TAYLORSWIFT | 11 | "Anti-Hero" singer who was honored with the People's Choice Award for The Female Artist of 2022 (2 wds.) |
| 48% | 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.) |
| 46% | 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.) |
| 46% | HARRYSTYLES | 11 | "As It Was" singer who was honored with the People's Choice Award for The Male Artist of 2022 (2 wds.) |
| 46% | JENNIFERLOPEZ | 13 | 15-Across and 27-Across singer who was the first woman honored with a "Billboard" Icon Award (2 wds) |
| 45% | TAYLORSWIFT | 11 | "Love Story" singer-songwriter who won the award for Top Female Artist in Billboard 2018: 2 wds. |
| 45% | JONIMITCHELL | 12 | 15-Across and 44-Across singer-songwriter who was honored with a Gershwin Award in 2023 (2 wds.) |
| 44% | LUKECOMBS | 9 | 15-Across and 33-Across singer who won the 2019 Country Music Association's New Artist of the Year Award (2 wds.) |
| 44% | TANYATUCKER | 11 | "Delta Dawn" singer who was honored as the 1972 Academy of Country Music's Most Promising Female Vocalist (2 wds.) |
| 43% | DIERKSBENTLEY | 13 | Singer of 15-Across and 29-Across who was awarded the 2018 Academy of Country Music's Merle Haggard Spirit Award (2 wds.) |
| 43% | BILLIEEILISH | 12 | "Bad Guy," 17-Across, and 42-Across singer who won Best New Artist at the 2019 MTV Video Music Awards (2 wds.) |
| 42% | HARRYSTYLES | 11 | "As It Was" singer who is nominated for a 2022 American Music Award for Artist of the Year (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% | BADBUNNY | 8 | "Dákiti" singer who won five Billboard Music Awards, including Top Latin Artist, in 2021 (2 wds.) |
| 41% | GABBYBARRETT | 12 | "I Hope" singer who won three Billboard Music Awards, including Top Country Female Artist, in 2021 (2 wds.) |
| 40% | SOLANGEKNOWLES | 14 | 12-Across and 28-Across singer who was the first recipient of the "Billboard" Women in Music Impact Award (2 wds.) |
| 40% | HARRYSTYLES | 11 | "As It Was" singer who won the People's Choice Award for Male Artist of 2022: 2 wds. |
| 39% | CYNDILAUPER | 11 | "Time After Time" singer who was honored with the "Billboard" Women in Music Icon Award in 2018 (2 wds.) |
| 39% | TAYLORSWIFT | 11 | "Anti-Hero" singer who is nominated for a 2022 American Music Award for Artist of the Year (2 wds.) |
| 39% | JENNIFERLOPEZ | 13 | "If You Had My Love" singer who was honored with the "Billboard" Women in Music Icon Award in 2020 (2 wds.) |
| 39% | SHANIATWAIN | 11 | "That Don't Impress Me Much" singer who was honored with the "Billboard" Women in Music Icon Award in 2016 (2 wds.) |
| 38% | IVAN | 4 | Cornejo who won New Artist of the Year at the 2022 Billboard Latin Music Awards |
| 38% | JOSEFELICIANO | 13 | "Feliz Navidad" singer who received the Billboard Latin Music Lifetime Achievement Award in 1996: 2 wds. |
| 38% | SEBASTIANYATRA | 14 | "Dos Oruguitas" singer who won the 2022 American Music Award for Favorite Latin Song (2 wds.) |
| 38% | PATSYCLINE | 10 | American singer (birthday today) who was the first female solo artist inducted to the Country Music Hall of Fame: 2 wds. |
| 38% | LORETTALYNN | 11 | "Coal Miner's Daughter" singer who was honored as the 1972 Country Music Association's Entertainer of the Year (2 wds.) |
| 38% | TAYLORSWIFT | 11 | "Lavender Haze" singer who won the People's Choice Award for Female Artist of 2022: 2 wds. |