| 100% | TAYLORSWIFT | 11 | "Better Man" songwriter who won the 2017 CMA Award for Song of the Year (2 wds.) |
| 73% | GARTHBROOKS | 11 | "Ask Me How I Know" singer who won the 2017 CMA Award for Entertainer of the Year (2 wds.) |
| 69% | GARTHBROOKS | 11 | "The Dance" singer who won the 2016 CMA Award for Entertainer of the Year: 2 wds. |
| 67% | MARENMORRIS | 11 | "Girl" singer who won the 2019 CMA Award for Album of the Year (2 wds.) |
| 65% | GARTHBROOKS | 11 | "That Girl Is a Cowboy" singer who won the 2019 CMA Award for Entertainer of the Year (2 wds.) |
| 65% | OLDDOMINION | 11 | "One Man Band" quintet who won the 2021 CMA Award for Vocal Group of the Year (2 wds.) |
| 65% | DWAYNEJOHNSON | 13 | "Hobbs & Shaw" actor who won the NAACP Image Award for Entertainer of the Year in 2017: 2 wds. |
| 64% | 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.) |
| 64% | 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.) |
| 59% | WILLSMITH | 9 | "Ali" actor who won the NAACP Image Award for Entertainer of the Year in 1999: 2 wds. |
| 59% | JAMIEFOXX | 9 | "Ray" actor who won the NAACP Image Award for Entertainer of the Year in 2013: 2 wds. |
| 59% | ASHLEYMCBRYDE | 13 | "Girl Going Nowhere" singer who won the 2019 CMA Award for New Artist of the Year (2 wds.) |
| 58% | GARTHBROOKS | 11 | "The River" singer who won the CMA Award for Entertainer of the Year seven times: 2 wds. |
| 58% | BILLIEEILISH | 12 | "What Was I Made For?" singer/co-songwriter who won Song of the Year at the 2024 Grammy Awards (2 wds.) |
| 58% | ALANJACKSON | 11 | "Country Boy" singer who won the CMA Award for Entertainer of the Year three times: 2 wds. |
| 58% | KENNYCHESNEY | 12 | "Come Over" singer who won the CMA Award for Entertainer of the Year four times: 2 wds. |
| 56% | LITTLEBIGTOWN | 13 | "Girl Crush" singers who won the 2016 CMA Award for Vocal Group of the Year: 3 wds. |
| 56% | DAKPRESCOTT | 11 | Dallas Cowboys quarterback who won the 2022 Walter Payton NFL Man of the Year award: 2 wds. |
| 56% | LEONARDCOHEN | 12 | Singer-songwriter in the Canadian Music Hall of Fame who won the 2017 Album of the Year Juno Award for "You Want It Darker" (2 wds.) |
| 56% | GARTHBROOKS | 11 | "The Dance" country singer who won the 2019 CMA for Entertainer of the Year: 2 wds. |
| 56% | ISAACHAYES | 10 | "Soul Man" singer who won an Academy Award for Best Original Song for his work on the film "Shaft": 2 wds. |
| 55% | MARENMORRIS | 11 | "My Church" singer who won the 2016 CMA New Artist of the Year award: 2 wds. |
| 55% | BRETTELDREDGE | 13 | "Lose My Mind" singer who won the 2014 CMA New Artist of the Year award: 2 wds. |
| 55% | TAYLORSWIFT | 11 | "Shake It Off" singer who won the 2007 CMA New Artist of the Year award: 2 wds. |
| 55% | TRACYCHAPMAN | 12 | "Fast Car" songwriter who won Song of the Year at the 2023 Country Music Association Awards (2 wds.) |
| 54% | TAYLORSWIFT | 11 | Singer-songwriter whose "1989" won 2016's Grammy Award for Album of the Year (2 wds.) |
| 53% | DAKPRESCOTT | 11 | Dallas Cowboys quarterback who won the 2022 Walter Payton NFL Man of the Year Award (2 wds.) |
| 53% | LITTLEBIGTOWN | 13 | "Better Man" singers who have won the Country Music Association Award for Vocal Group of the Year six times (3 wds.) |
| 53% | SHAWNMENDES | 11 | "Señorita" singer who won Canada's Juno Award for Pop Album of the Year in 2019: 2 wds. |
| 53% | TONYBENNETT | 11 | "Rags to Riches" singer who won the 2017 Library of Congress Gershwin Prize for Popular Song: 2 wds. |