| 100% | JASONALDEAN | 11 | "You Make It Easy" country singer named the ACM Artist of the Decade for the 2010s: 2 wds. |
| 76% | JASONALDEAN | 11 | Country singer named ACM's Artist of the Decade for the 2010s in 2019 (2 wds.) |
| 76% | GARTHBROOKS | 11 | "The Dance" country singer named the ACM Artist of the Decade for the 1990s: 2 wds. |
| 75% | GEORGESTRAIT | 12 | "I Cross My Heart" country singer named the ACM Artist of the Decade for the 2000s: 2 wds. |
| 62% | JASONALDEAN | 11 | 17-Across and 30-Across country singer who was named ACM's Artist of the Decade for the 2010s (2 wds.) |
| 54% | JASONALDEAN | 11 | "You Make It Easy" singer who won Entertainer of the Year at the 2018 Academy of Country Music Awards: 2 wds. |
| 46% | RASCALFLATTS | 12 | "Yours If You Want It" singers who have won the Country Music Association Award for Vocal Group of the Year six times (2 wds.) |
| 45% | HARRYSTYLES | 11 | "As It Was" singer who won the People's Choice Award for Male Artist of 2022: 2 wds. |
| 42% | ARIANAGRANDE | 12 | Singer recently named Breakthrough Artist of the Year by the Music Business Association: 2 wds. |
| 42% | PAPERWASP | 9 | Flying insect named for the type of 17-Across it makes (2 wds.) |
| 41% | GARTHBROOKS | 11 | "The Dance" country singer who won the 2019 CMA for Entertainer of the Year: 2 wds. |
| 41% | DIANAROSS | 9 | "Stop! In the Name of Love" singer named one of People's Most Beautiful for 2017: 2 wds. |
| 40% | HARRYSTYLES | 11 | "As It Was" singer who is nominated for a 2022 American Music Award for Artist of the Year (2 wds.) |
| 40% | RASCALFLATTS | 12 | "Yours If You Want It" band nominated for the 2017 Country Music Award for Vocal Group of the Year (2 wds.) |
| 40% | EDSHEERAN | 9 | "Shape Of You" artist who won the award for the Top Male Artist in Billboard 2018: 2 wds. |
| 40% | JELLYROLL | 9 | "Need a Favor" country singer who was nominated for Best New Artist at the 2024 Grammys: 2 wds. |
| 39% | HARRYSTYLES | 11 | "As It Was" singer who was honored with the People's Choice Award for The Male Artist of 2022 (2 wds.) |
| 39% | CARDIB | 6 | Featured artist on Maroon 5's "Girls Like You," the #5 song of the 2010s: 2 wds. |
| 39% | TAYLORSWIFT | 11 | "Shake It Off" singer who won the 2007 CMA New Artist of the Year award: 2 wds. |
| 39% | TAYLORSWIFT | 11 | "You Need to Calm Down" singer who won six 2019 American Music Awards, including Artist of the Decade (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% | 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% | CARLYPEARCE | 11 | "I Hope You're Happy Now" singer/songwriter who won the 2021 Country Music Association Award for Female Vocalist of the Year (2 wds.) |
| 38% | ATIP | 4 | "It was nice of you to leave ___ for the waiter.": 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% | LUKECOMBS | 9 | "Forever After All" country singer whose "The Kind of Love We Make" hit the Billboard Top 10 in 2022: 2 wds. |
| 38% | TAYLORSWIFT | 11 | "Lavender Haze" singer who won the People's Choice Award for Female Artist of 2022: 2 wds. |
| 38% | JASONALDEAN | 11 | "Burnin' It Down" singer who won Entertainer of the Year at the 2016, 2017, and 2018 ACM Awards: 2 wds. |