| 100% | KENNYCHESNEY | 12 | "Come Over" singer who won the CMA Award for Entertainer of the Year four times: 2 wds. |
| 84% | GARTHBROOKS | 11 | "The River" singer who won the CMA Award for Entertainer of the Year seven times: 2 wds. |
| 83% | ALANJACKSON | 11 | "Country Boy" singer who won the CMA Award for Entertainer of the Year three times: 2 wds. |
| 67% | GARTHBROOKS | 11 | "The Dance" singer who won the 2016 CMA Award for Entertainer of the Year: 2 wds. |
| 67% | GARTHBROOKS | 11 | "The Dance" country singer who won the 2019 CMA 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% | 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.) |
| 56% | CHRISSTAPLETON | 14 | "Starting Over" singer/songwriter who won the 2021 CMA Awards for Male Vocalist of the Year, Album of the Year, Single of the Year, and Song of the Year (2 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% | MILEYCYRUS | 10 | Singer who won Video of the Year for "Wrecking Ball" at MTV Video Music Awards in 2014: 2 wds. |
| 53% | BRITNEYSPEARS | 13 | Singer who won Video of the Year for "Piece of Me" at MTV Video Music Awards in 2008: 2 wds. |
| 53% | DWAYNEJOHNSON | 13 | "Hobbs & Shaw" actor who won the NAACP Image Award for Entertainer of the Year in 2017: 2 wds. |
| 53% | SHAWNMENDES | 11 | "Señorita" singer who won Canada's Juno Award for Pop Album of the Year in 2019: 2 wds. |
| 52% | THOMASRHETT | 11 | "Country Again" singer who won Entertainer of the Year at the 2020 Academy of Country Music Awards: 2 wds. |
| 52% | 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.) |
| 52% | JASONALDEAN | 11 | "Burnin' It Down" singer who won Entertainer of the Year at the 2016, 2017, and 2018 ACM Awards: 2 wds. |
| 52% | OLDDOMINION | 11 | "One Man Band" quintet who won the 2021 CMA Award for Vocal Group of the Year (2 wds.) |
| 52% | JASONALDEAN | 11 | "You Make It Easy" singer who won Entertainer of the Year at the 2018 Academy of Country Music Awards: 2 wds. |
| 52% | CONWAYTWITTY | 12 | Country Music Hall of Fame singer who shared four consecutive CMA Awards for Vocal Duo of the Year with 28-Across in the 1970s (2 wds.) |
| 51% | MARENMORRIS | 11 | "The Bones" country singer who won Female Vocalist of the Year at the 2020 CMAs: 2 wds. |
| 51% | 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.) |