| 100% | POSTMALONE | 10 | 18-Across, 27-Across, and 34-Across rapper/singer who won the 2025 American Music Award for Favorite Country Male Artist (2 wds.) |
| 66% | GARTHBROOKS | 11 | Country Music Hall of Fame singer who's won the American Music Award for Favorite Male Country Artist a record eight times (2 wds.) |
| 61% | 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.) |
| 58% | KENNYROGERS | 11 | Country Music Hall of Fame singer who's won the American Music Award for Favorite Country Single a record five times (2 wds.) |
| 56% | POSTMALONE | 10 | 18-Across, 27-Across, and 34-Across rapper whose "Rockstar" won the 2018 Billboard Music Award for Top Rap Song and the 2018 MTV Video Music Award for Song of the Year (2 wds.) |
| 55% | CARDIB | 6 | "Up" rapper who won the American Music Award for Favorite Rap/Hip-Hop Artist twice: 2 wds. |
| 55% | NICKIMINAJ | 10 | "Anaconda" rapper who won the American Music Award for Favorite Rap/Hip-Hop Artist four times: 2 wds. |
| 55% | IGGYAZALEA | 10 | "Fancy" rapper who won the American Music Award for Favorite Rap/Hip-Hop Artist in 2014: 2 wds. |
| 55% | SEBASTIANYATRA | 14 | "Dos Oruguitas" singer who won the 2022 American Music Award for Favorite Latin Song (2 wds.) |
| 53% | BEYONCE | 7 | "Renaissance" singer who won the 2022 American Music Award for Favorite Female R&B Artist |
| 52% | 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.) |
| 52% | CLINTBLACK | 10 | 18-Across, 26-Across, and 35-Across country singer who won four 1989 Academy of Country Music Awards, including Top Male Vocalist (2 wds.) |
| 50% | MORGANWALLEN | 12 | 15-Across, 38-Across, and "7 Summers" singer who won the iHeartRadio Music Awards Best New Country Artist in 2020 (2 wds.) |
| 50% | LUKECOMBS | 9 | 15-Across and 33-Across singer who won the 2019 Country Music Association's New Artist of the Year Award (2 wds.) |
| 50% | HARRYSTYLES | 11 | "As It Was" singer who won the People's Choice Award for Male Artist of 2022: 2 wds. |
| 48% | JANELLEMONAE | 12 | "Dirty Computer" singer who won the GLAAD Media Award for Outstanding Music Artist in 2019: 2 wds. |
| 48% | SAMSMITH | 8 | "Love Goes" singer who won the GLAAD Media Award for Outstanding Music Artist in 2021: 2 wds. |
| 47% | LADYGAGA | 8 | "Born This Way" singer who won the GLAAD Media Award for Outstanding Music Artist in 2012: 2 wds. |
| 47% | TAYLORSWIFT | 11 | "You Need to Calm Down" singer who won six 2019 American Music Awards, including Artist of the Decade (2 wds.) |
| 46% | EMINEM | 6 | "Lucky You" rapper who won the American Music Award for Favorite Rap/Hip-Hop Artist four times |
| 45% | OLDTOWNROAD | 11 | Lil Nas X and Billy Ray Cyrus song that won the 2019 American Music Award for Favorite Rap/Hip-Hop Song (3 wds.) |
| 45% | TAYLORSWIFT | 11 | "Lavender Haze" singer who won the People's Choice Award for Female Artist of 2022: 2 wds. |
| 45% | BILLIEEILISH | 12 | "Bad Guy," 17-Across, and 42-Across singer who won Best New Artist at the 2019 MTV Video Music Awards (2 wds.) |
| 44% | PEABOBRYSON | 11 | Singer/songwriter who won Grammy Awards for 34-Across and the "Beauty and the Beast" theme (2 wds.) |
| 44% | THOMASRHETT | 11 | 17-Across and 28-Across singer who was the 2019 Academy of Country Music's Male Artist of the Year (2 wds.) |
| 44% | BRANDICARLILE | 13 | 18-Across and 42-Across singer who won a Best Country Song Grammy Award for "Bring My Flowers Now" (2 wds.) |
| 44% | 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.) |
| 43% | KENDRICKLAMAR | 13 | Rapper/songwriter nominated for the 2017 American Music Award for Artist of the Year (2 wds.) |
| 42% | RODDYRICCH | 10 | "The Box" rapper who won the BET Award for Best New Artist in 2020: 2 wds. |
| 42% | 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.) |