| 100% | GEORGESTRAIT | 12 | "I Cross My Heart" country singer named the ACM Artist of the Decade for the 2000s: 2 wds. |
| 76% | GARTHBROOKS | 11 | "The Dance" country singer named the ACM Artist of the Decade for the 1990s: 2 wds. |
| 75% | JASONALDEAN | 11 | "You Make It Easy" country singer named the ACM Artist of the Decade for the 2010s: 2 wds. |
| 69% | JASONALDEAN | 11 | Country singer named ACM's Artist of the Decade for the 2010s in 2019 (2 wds.) |
| 57% | JASONALDEAN | 11 | 17-Across and 30-Across country singer who was named ACM's Artist of the Decade for the 2010s (2 wds.) |
| 46% | LUKECOMBS | 9 | Singer of the 2019 country hit "Beer Never Broke My Heart": 2 wds. |
| 44% | TONYBENNETT | 11 | 2018 AP Coach of the Year who shares his name with the singer of "I Left My Heart in San Francisco": 2 wds. |
| 43% | MICKEYGUYTON | 12 | "Black Like Me" singer who was the second Black country artist to cohost the ACM Awards (2021): 2 wds. |
| 42% | ARIANAGRANDE | 12 | Singer recently named Breakthrough Artist of the Year by the Music Business Association: 2 wds. |
| 42% | NORAHJONES | 10 | "Come Away With Me" singer who received the Grammys for both Album of the Year and Best New Artist in 2003: 2 wds. |
| 41% | GARTHBROOKS | 11 | "The Dance" country singer who won the 2019 CMA for Entertainer of the Year: 2 wds. |
| 41% | JOHNLEGEND | 10 | "All of Me" singer named People magazine's Sexiest Man Alive for 2019: 2 wds. |
| 41% | DIANAROSS | 9 | "Stop! In the Name of Love" singer named one of People's Most Beautiful for 2017: 2 wds. |
| 40% | TOBYKEITH | 9 | Singer (with Willie Nelson) of the 2003 song "Beer for My Horses": 2 wds. |
| 40% | JELLYROLL | 9 | "Need a Favor" country singer who was nominated for Best New Artist at the 2024 Grammys: 2 wds. |
| 39% | BRETTELDREDGE | 13 | "Lose My Mind" singer who won the 2014 CMA New Artist of the Year award: 2 wds. |
| 39% | BRITNEYSPEARS | 13 | Singer who won Video of the Year for "Piece of Me" at MTV Video Music Awards in 2008: 2 wds. |
| 39% | TONYBENNETT | 11 | "I Left My Heart in San Francisco" singer honored with the 2017 Gershwin Prize for Popular Song (2 wds.) |
| 39% | JACKSONBROWNE | 13 | "Doctor, My Eyes" singer whose first name is the capital of Mississippi: 2 wds. |
| 39% | ALJARREAU | 9 | Singer whose "Moonlighting" was the theme song for the TV show of the same name: 2 wds. |
| 38% | THEWEEKND | 9 | Stage name of "Starboy" singer who used the name for anonymity on YouTube: 2 wds. |
| 38% | JLO | 3 | Nickname of the singer known for "All I Have" and "On the Floor": 2 wds. |
| 38% | GARTHBROOKS | 11 | Country Music Hall of Fame singer who's won the American Music Award for Favorite Male Country Artist a record eight times (2 wds.) |
| 38% | REBAMCENTIRE | 12 | Country Music Hall of Fame singer who's won the American Music Award for Favorite Female Country Artist a record 11 times (2 wds.) |
| 38% | TOBYKEITH | 9 | Singer who duetted with Willie Nelson on the 2003 #1 country hit "Beer for My Horses": 2 wds. |
| 38% | HARRYSTYLES | 11 | "As It Was" singer who won the People's Choice Award for Male Artist of 2022: 2 wds. |
| 38% | WHITNEYHOUSTON | 14 | "Saving All My Love for You" singer in the Rock and Roll Hall of Fame whose last name is a city in Texas (2 wds.) |
| 38% | SHERYLCROW | 10 | "All I Wanna Do" singer who won the Best New Artist and Record of the Year Grammys in 1995: 2 wds. |
| 38% | TAYLORSWIFT | 11 | "Lavender Haze" singer who won the People's Choice Award for Female Artist of 2022: 2 wds. |
| 37% | ALGREEN | 7 | Singer whose name is an anagram of the word "general": 2 wds. |