| 100% | ALANJACKSON | 11 | "Country Boy" singer who won the CMA Award for Entertainer of the Year three times: 2 wds. |
| 84% | GARTHBROOKS | 11 | "The River" singer who won the CMA Award for Entertainer of the Year seven times: 2 wds. |
| 83% | KENNYCHESNEY | 12 | "Come Over" singer who won the CMA Award for Entertainer of the Year four times: 2 wds. |
| 72% | GARTHBROOKS | 11 | "The Dance" country singer who won the 2019 CMA for Entertainer of the Year: 2 wds. |
| 67% | GARTHBROOKS | 11 | "The Dance" singer who won the 2016 CMA Award for Entertainer of the Year: 2 wds. |
| 62% | GARTHBROOKS | 11 | "Ask Me How I Know" singer who won the 2017 CMA Award for Entertainer of the Year (2 wds.) |
| 62% | GARTHBROOKS | 11 | "That Girl Is a Cowboy" singer who won the 2019 CMA Award for Entertainer of the Year (2 wds.) |
| 60% | BRETTELDREDGE | 13 | "Lose My Mind" singer who won the 2014 CMA New Artist of the Year award: 2 wds. |
| 60% | TAYLORSWIFT | 11 | "Shake It Off" singer who won the 2007 CMA New Artist of the Year award: 2 wds. |
| 60% | MARENMORRIS | 11 | "My Church" singer who won the 2016 CMA New Artist of the Year award: 2 wds. |
| 59% | THOMASRHETT | 11 | "Country Again" singer who won Entertainer of the Year at the 2020 Academy of Country Music Awards: 2 wds. |
| 59% | ASHLEYMCBRYDE | 13 | "Girl Going Nowhere" singer who won the 2019 CMA Award for New Artist of the Year (2 wds.) |
| 58% | MARENMORRIS | 11 | "Girl" singer who won the 2019 CMA Award for Album of the Year (2 wds.) |
| 58% | RASCALFLATTS | 12 | "Yours If You Want It" singers who have won the Country Music Association Award for Vocal Group of the Year six times (2 wds.) |
| 57% | JASONALDEAN | 11 | "You Make It Easy" singer who won Entertainer of the Year at the 2018 Academy of Country Music Awards: 2 wds. |
| 57% | MARENMORRIS | 11 | "The Bones" country singer who won Female Vocalist of the Year at the 2020 CMAs: 2 wds. |
| 56% | 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.) |
| 56% | MIRANDALAMBERT | 14 | "Bluebird" country singer who won Music Video of the Year at the 2020 CMAs: 2 wds. |
| 56% | LITTLEBIGTOWN | 13 | "Better Man" singers who have won the Country Music Association Award for Vocal Group of the Year six times (3 wds.) |
| 55% | LITTLEBIGTOWN | 13 | "Girl Crush" singers who won the 2016 CMA Award for Vocal Group of the Year: 3 wds. |
| 55% | MIRANDALAMBERT | 14 | "Settling Down" singer who won Entertainer of the Year at the 2022 ACM Awards: 2 wds. |
| 55% | CHRISSTAPLETON | 14 | "From a Room: Volume 1" singer who won the 2017 CMA Awards for Male Vocalist of the Year and Album of the Year (2 wds.) |
| 54% | WILLSMITH | 9 | "Ali" actor who won the NAACP Image Award for Entertainer of the Year in 1999: 2 wds. |
| 54% | JAMIEFOXX | 9 | "Ray" actor who won the NAACP Image Award for Entertainer of the Year in 2013: 2 wds. |
| 53% | 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.) |
| 53% | MIRANDALAMBERT | 14 | "Tin Man" singer who won Female Vocalist of the Year at the 2018 Academy of Country Music Awards: 2 wds. |
| 53% | 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.) |
| 53% | MILEYCYRUS | 10 | Singer who won Video of the Year for "Wrecking Ball" at MTV Video Music Awards in 2014: 2 wds. |
| 53% | 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.) |
| 53% | 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.) |