| 100% | JASONALDEAN | 11 | 17-Across and 30-Across country singer who was named ACM's Artist of the Decade for the 2010s (2 wds.) |
| 62% | JASONALDEAN | 11 | Country singer named ACM's Artist of the Decade for the 2010s in 2019 (2 wds.) |
| 59% | JASONALDEAN | 11 | "You Make It Easy" country singer named the ACM Artist of the Decade for the 2010s: 2 wds. |
| 58% | THOMASRHETT | 11 | 17-Across and 28-Across singer who was the 2019 Academy of Country Music's Male Artist of the Year (2 wds.) |
| 56% | ARIANAGRANDE | 12 | 17-Across and 39-Across singer who was named Billboard's 2018 Woman of the Year (2 wds.) |
| 55% | GARTHBROOKS | 11 | "The Dance" country singer named the ACM Artist of the Decade for the 1990s: 2 wds. |
| 54% | GEORGESTRAIT | 12 | "I Cross My Heart" country singer named the ACM Artist of the Decade for the 2000s: 2 wds. |
| 50% | MARENMORRIS | 11 | 1-Across, 12-Across, 27-Across, and 50-Across country/pop singer who was named Female Vocalist of the Year by the Country Music Association in 2020 (2 wds.) |
| 50% | JENNIFERLOPEZ | 13 | "Let's Get Loud" singer who was named Glamour Woman of the Year in 1999 and 2011: 2 wds. |
| 50% | TAYLORSWIFT | 11 | Seven-time Grammy-winning country and pop singer who was EW's 2010 Entertainer of the Year: 2 wds. |
| 49% | 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.) |
| 49% | 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.) |
| 48% | HARRYSTYLES | 11 | "As It Was" singer who won the People's Choice Award for Male Artist of 2022: 2 wds. |
| 48% | 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. |
| 48% | LAURYNHILL | 10 | "Everything Is Everything" singer who received the Grammys for both Album of the Year and Best New Artist in 1999: 2 wds. |
| 47% | JELLYROLL | 9 | "Need a Favor" country singer who was nominated for Best New Artist at the 2024 Grammys: 2 wds. |
| 47% | HARRYSTYLES | 11 | "As It Was" singer who was honored with the People's Choice Award for The Male Artist of 2022 (2 wds.) |
| 47% | TAYLORSWIFT | 11 | "Anti-Hero" singer who was honored with the People's Choice Award for The Female Artist of 2022 (2 wds.) |
| 46% | LUKECOMBS | 9 | 15-Across and 33-Across singer who won the 2019 Country Music Association's New Artist of the Year Award (2 wds.) |
| 46% | JOHNLEGEND | 10 | "All of Me" singer and "The Voice" coach who was named People's Sexiest Man Alive in 2019: 2 wds. |
| 45% | MICKEYGUYTON | 12 | "Black Like Me" singer who was the second Black country artist to cohost the ACM Awards (2021): 2 wds. |
| 45% | BLAKESHELTON | 12 | Country singer and "The Voice" judge who is People's Sexiest Man Alive of 2017: 2 wds. |
| 44% | BLAKESHELTON | 12 | "God's Country" singer and "The Voice" coach who was named People's Sexiest Man Alive in 2017: 2 wds. |
| 44% | DIANAROSS | 9 | American singer who was the lead singer of "The Supremes" and is known for her solo songs like "Upside Down": 2 wds. |
| 44% | PARISJACKSON | 12 | The King of Pop's daughter who was recently named an ambassador for the Elizabeth Taylor AIDS Foundation: 2 wds. |
| 44% | 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 |
| 43% | KACEYMUSGRAVES | 14 | 19-Across and 46-Across singer who won four 2019 Grammys, including Album of the Year and Best Country Album for "Golden Hour" (2 wds.) |
| 43% | JOHNCALIPARI | 12 | University of Kentucky basketball coach who is the subject of the 2017 ESPN "30 for 30" documentary "One and Not Done": 2 wds. |
| 43% | DIERKSBENTLEY | 13 | Singer of 15-Across and 29-Across who was honored with an Academy of Country Music's Merle Haggard Spirit Award (2 wds.) |
| 43% | PATSYCLINE | 10 | American singer (birthday today) who was the first female solo artist inducted to the Country Music Hall of Fame: 2 wds. |