| 100% | LUKEBRYAN | 9 | "Strip It Down" singer and 2015 CMA Entertainer of the Year: 2 wds. |
| 62% | JASONALDEAN | 11 | "Burnin' It Down" singer who won Entertainer of the Year at the 2016, 2017, and 2018 ACM Awards: 2 wds. |
| 51% | MIRANDALAMBERT | 14 | "Settling Down" singer who won Entertainer of the Year at the 2022 ACM Awards: 2 wds. |
| 50% | ERICCHURCH | 10 | "Mr. Misunderstood" singer nominated for the 2020 CMA Entertainer of the Year (2 wds.) |
| 49% | GARTHBROOKS | 11 | "The Dance" singer who won the 2016 CMA Award for Entertainer of the Year: 2 wds. |
| 49% | GARTHBROOKS | 11 | "The Dance" country singer who won the 2019 CMA for Entertainer of the Year: 2 wds. |
| 49% | SANDRABULLOCK | 13 | Actress who was EW's only two-time Entertainer of the Year, in 2009 and 2013: 2 wds. |
| 48% | NOVAKDJOKOVIC | 13 | Serbian tennis player who was Laureus sportsman of the year 2016 and 2015: 2 wds. |
| 48% | MIRANDALAMBERT | 14 | "It All Comes Out in the Wash" singer nominated for the 2020 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. |
| 47% | JASONALDEAN | 11 | "You Make It Easy" singer who won Entertainer of the Year at the 2018 Academy of Country Music Awards: 2 wds. |
| 47% | ALANJACKSON | 11 | "Country Boy" singer who won the CMA Award for Entertainer of the Year three times: 2 wds. |
| 47% | KENNYCHESNEY | 12 | "Come Over" singer who won the CMA Award for Entertainer of the Year four times: 2 wds. |
| 47% | KEITHURBAN | 10 | "Blue Ain't Your Color" singer nominated for the 2020 CMA Entertainer of the Year (2 wds.) |
| 46% | THEWEEKND | 9 | Singer of the 2015 pop song "Earned It," which sounds like a waltz: 2 wds. |
| 44% | JODIEFOSTER | 11 | Two-time Oscar-winning actress who was Entertainment Weekly's 1991 Entertainer of the Year: 2 wds. |
| 44% | TAYLORSWIFT | 11 | "Shake It Off" singer who won the 2007 CMA New Artist of the Year award: 2 wds. |
| 43% | TAYLORSWIFT | 11 | Seven-time Grammy-winning country and pop singer who was EW's 2010 Entertainer of the Year: 2 wds. |
| 43% | MIRANDALAMBERT | 14 | "Bluebird" country singer who won Music Video of the Year at the 2020 CMAs: 2 wds. |
| 43% | THOMASRHETT | 11 | "Country Again" singer who won Entertainer of the Year at the 2020 Academy of Country Music Awards: 2 wds. |
| 42% | MARENMORRIS | 11 | "The Bones" country singer who won Female Vocalist of the Year at the 2020 CMAs: 2 wds. |
| 42% | GARTHBROOKS | 11 | "Ask Me How I Know" singer who won the 2017 CMA Award for Entertainer of the Year (2 wds.) |
| 42% | GARTHBROOKS | 11 | "That Girl Is a Cowboy" singer who won the 2019 CMA Award for Entertainer of the Year (2 wds.) |
| 41% | CAITLYNJENNER | 13 | Transgender rights activist who was named Glamour Woman of the Year in 2015: 2 wds. |
| 41% | BARACKOBAMA | 11 | Political victor who was Time's Person of the Year in 2008 and 2012: 2 wds. |
| 41% | IGASWIATEK | 10 | Polish tennis player who won WTA Player of the Year in 2022 and 2023: 2 wds. |
| 41% | ASHLEIGHBARTY | 13 | Australian tennis player who won WTA Player of the Year in 2019 and 2021: 2 wds. |
| 40% | ARIANAGRANDE | 12 | Singer of the #1 hits "Thank U, Next" and "7 Rings": 2 wds. |
| 40% | LADYGAGA | 8 | Singer of the #1 hits "Just Dance" and "Born This Way": 2 wds. |
| 40% | VIJAYSINGH | 10 | Golfer who won both PGA Tour Player of the Year and Rookie of the Year awards: 2 wds. |