| 100% | JAMIEFOXX | 9 | "Ray" actor who won the NAACP Image Award for Entertainer of the Year in 2013: 2 wds. |
| 89% | WILLSMITH | 9 | "Ali" actor who won the NAACP Image Award for Entertainer of the Year in 1999: 2 wds. |
| 88% | DWAYNEJOHNSON | 13 | "Hobbs & Shaw" actor who won the NAACP Image Award for Entertainer of the Year in 2017: 2 wds. |
| 61% | GARTHBROOKS | 11 | "The Dance" singer who won the 2016 CMA Award for Entertainer of the Year: 2 wds. |
| 57% | GARTHBROOKS | 11 | "Ask Me How I Know" singer who won the 2017 CMA Award for Entertainer of the Year (2 wds.) |
| 57% | GARTHBROOKS | 11 | "That Girl Is a Cowboy" singer who won the 2019 CMA Award for Entertainer of the Year (2 wds.) |
| 55% | GARTHBROOKS | 11 | "The River" singer who won the CMA Award for Entertainer of the Year seven times: 2 wds. |
| 55% | ALANJACKSON | 11 | "Country Boy" singer who won the CMA Award for Entertainer of the Year three times: 2 wds. |
| 55% | KENNYCHESNEY | 12 | "Come Over" singer who won the CMA Award for Entertainer of the Year four times: 2 wds. |
| 55% | MARIANORIVERA | 13 | Yankees relief pitcher who won the MLB Comeback Player of the Year Award in 2013: 2 wds. |
| 54% | SHAWNMENDES | 11 | "Señorita" singer who won Canada's Juno Award for Pop Album of the Year in 2019: 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% | DAVIDOYELOWO | 12 | 19-Across and 33-Across actor who won a 2015 NAACP Image Award for his portrayal of Martin Luther King Jr. in "Selma" (2 wds.) |
| 53% | SERENAWILLIAMS | 14 | Tennis player who won the AP Athlete of the Year award in 2002, 2009, 2013, and 2015: 2 wds. |
| 52% | JODIEFOSTER | 11 | Actress who won a Golden Globe for "The Silence of the Lambs" and won their Cecil B. DeMille Award in 2013: 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% | MARENMORRIS | 11 | "Girl" singer who won the 2019 CMA Award for Album of the Year (2 wds.) |
| 51% | TAYLORSWIFT | 11 | "Better Man" songwriter who won the 2017 CMA Award for Song of the Year (2 wds.) |
| 51% | BENKINGSLEY | 11 | Actor born in England who won the Academy Award for Best Actor for his portrayal of Mahatma Gandhi in the movie "Gandhi": 2 wds. |
| 50% | SANDRABULLOCK | 13 | Actress who was EW's only two-time Entertainer of the Year, in 2009 and 2013: 2 wds. |
| 49% | SAMMENDES | 9 | "The Ferryman" director who won the Tony Award for Best Direction of a Play in 2019 (2 wds.) |
| 49% | PRINCEFIELDER | 13 | Rangers designated hitter who won the MLB Comeback Player of the Year Award in 2015: 2 wds. |
| 49% | CORBINCARROLL | 13 | Diamondbacks outfielder who won the National League Rookie of the Year Award in 2023: 2 wds. |
| 49% | JONATHANINDIA | 13 | Reds infielder who won the National League Rookie of the Year Award in 2021: 2 wds. |
| 49% | RICKTOCCHET | 11 | Vancouver Canucks head coach who was honored with the NHL's Jack Adams Award for coach of the year in 2024 (2 wds.) |
| 49% | RUDYGOBERT | 10 | Jazz center who won his second consecutive Defensive Player of the Year Award in 2019: 2 wds. |
| 48% | PERCYFAITH | 10 | Bandleader/orchestrator whose instrumental version of "Theme from 'A Summer Place'" won a Grammy Award for Record of the Year in 1961 (2 wds.) |
| 48% | JEREMYIRONS | 11 | "Eragon" actor who won the 2014 Primetime Emmy Award for Outstanding Narrator for "Game of Lions": 2 wds. |
| 48% | KAWHILEONARD | 12 | Clippers small forward who won his second consecutive Defensive Player of the Year Award in 2016: 2 wds. |
| 48% | JOHNLITHGOW | 11 | "3rd Rock From the Sun" actor who won a Tony Award for "Sweet Smell of Success": 2 wds. |