| 100% | JASONALDEAN | 11 | "Burnin' It Down" singer who won Entertainer of the Year at the 2016, 2017, and 2018 ACM Awards: 2 wds. |
| 72% | JASONALDEAN | 11 | "You Make It Easy" singer who won Entertainer of the Year at the 2018 Academy of Country Music Awards: 2 wds. |
| 71% | MIRANDALAMBERT | 14 | "Settling Down" singer who won Entertainer of the Year at the 2022 ACM Awards: 2 wds. |
| 62% | THOMASRHETT | 11 | "Country Again" singer who won Entertainer of the Year at the 2020 Academy of Country Music Awards: 2 wds. |
| 54% | GARTHBROOKS | 11 | "The Dance" singer who won the 2016 CMA Award for Entertainer of the Year: 2 wds. |
| 53% | BRUNOMARS | 9 | "24K Magic" singer who won six awards, including Record of the Year, at the 2018 Grammy Awards (2 wds.) |
| 53% | THEWEEKND | 9 | "Blinding Lights" singer who won Video of the Year and Best R&B at the 2020 MTV Video Music Awards (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. |
| 52% | MILEYCYRUS | 10 | Singer who won Video of the Year for "Wrecking Ball" at MTV Video Music Awards in 2014: 2 wds. |
| 52% | BRITNEYSPEARS | 13 | Singer who won Video of the Year for "Piece of Me" at MTV Video Music Awards in 2008: 2 wds. |
| 50% | GARTHBROOKS | 11 | "Ask Me How I Know" singer who won the 2017 CMA Award for Entertainer of the Year (2 wds.) |
| 50% | 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.) |
| 49% | BILLIEEILISH | 12 | "What Was I Made For?" singer/co-songwriter who won Song of the Year at the 2024 Grammy Awards (2 wds.) |
| 49% | LADYGAGA | 8 | "Rain on Me" singer who won the MTV Tricon Award, Artist of the Year, and two other awards at the 2020 MTV Video Music Awards (2 wds.) |
| 49% | TAYLORSWIFT | 11 | "Shake It Off" singer who won the 2007 CMA New Artist of the Year award: 2 wds. |
| 49% | LUKEBRYAN | 9 | "Strip It Down" singer and 2015 CMA Entertainer of the Year: 2 wds. |
| 48% | GARTHBROOKS | 11 | "The River" singer who won the CMA Award for Entertainer of the Year seven times: 2 wds. |
| 48% | MARENMORRIS | 11 | "My Church" singer who won the 2016 CMA New Artist of the Year award: 2 wds. |
| 48% | 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.) |
| 48% | CAELEBDRESSEL | 13 | Seven-time Olympic swimming gold medalist who won Athlete of the Year at the Golden Goggle Awards three times: 2 wds. |
| 48% | MICHAELPHELPS | 13 | 23-time Olympic swimming gold medalist who won Athlete of the Year at the Golden Goggle Awards seven times: 2 wds. |
| 48% | ALANJACKSON | 11 | "Country Boy" singer who won the CMA Award for Entertainer of the Year three times: 2 wds. |
| 48% | KENNYCHESNEY | 12 | "Come Over" singer who won the CMA Award for Entertainer of the Year four times: 2 wds. |
| 48% | EDSHEERAN | 9 | "Shape of You" singer who won two awards, including Best Pop Vocal Album, at the 2018 Grammy Awards (2 wds.) |
| 48% | DWAYNEJOHNSON | 13 | "Hobbs & Shaw" actor who won the NAACP Image Award for Entertainer of the Year in 2017: 2 wds. |
| 48% | 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.) |
| 47% | KATIELEDECKY | 12 | Seven-time Olympic swimming gold medalist who won Female Athlete of the Year at the 2013-2018 and 2021 Golden Goggle Awards: 2 wds. |
| 47% | LUKECOMBS | 9 | 15-Across and 33-Across singer who won the 2019 Country Music Association's New Artist of the Year Award (2 wds.) |
| 47% | CHRISSTAPLETON | 14 | "Tennessee Whiskey" singer-songwriter who won Male Vocalist of the Year at the 2023 Country Music Association Awards (2 wds.) |
| 47% | OLDDOMINION | 11 | "Written in the Sand" band that won Vocal Group of the Year at the 2018 Academy of Country Music Awards: 2 wds. |