| 100% | GILL | 4 | Vince ___, "I Still Believe In You" singer who's won multiple Country Music Association Awards |
| 47% | 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% | VINCEGILL | 9 | "I Still Believe in You" country singer born in Norman, Oklahoma (2 wds.) |
| 44% | LITTLEBIGTOWN | 13 | "Better Man" singers who have won the Country Music Association Award for Vocal Group of the Year six times (3 wds.) |
| 44% | GABBYBARRETT | 12 | "I Hope" singer who won three Billboard Music Awards, including Top Country Female Artist, in 2021 (2 wds.) |
| 42% | 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.) |
| 42% | BRITNEYSPEARS | 13 | Singer who won Video of the Year for "Piece of Me" at MTV Video Music Awards in 2008: 2 wds. |
| 40% | MORGANWALLEN | 12 | 15-Across, 38-Across, and "7 Summers" singer who won the iHeartRadio Music Awards Best New Country Artist in 2020 (2 wds.) |
| 38% | BRUNOMARS | 9 | "24K Magic" singer who won the award for R&B Song, "That's What I Like" in Billboard 2018: 2 wds |
| 37% | LORI | 4 | Country/folk singer McKenna who won a CMA Award in 2016 |
| 37% | DAVID | 5 | ___ Bowie, English singer who won a Grammy Award for best music video in 1985 |
| 37% | TAYLORSWIFT | 11 | "Look What You Made Me Do" singer who has won the most Billboard Music Awards (23) (2 wds.) |
| 37% | LIONELRICHIE | 12 | Singer who won the Oscar in 1986 for Best Original Song, "Say You, Say Me": 2 wds. |
| 36% | BADBUNNY | 8 | "Dákiti" singer who won five Billboard Music Awards, including Top Latin Artist, in 2021 (2 wds.) |
| 36% | JASONALDEAN | 11 | "You Make It Easy" singer who won Entertainer of the Year at the 2018 Academy of Country Music Awards: 2 wds. |
| 36% | POPSMOKE | 8 | "What You Know Bout Love" singer who won five Billboard Music Awards, including Top New Artist, in 2021 (2 wds.) |
| 36% | MILEYCYRUS | 10 | Singer who won Video of the Year for "Wrecking Ball" at MTV Video Music Awards in 2014: 2 wds. |
| 36% | TIMBERLAKE | 10 | Justin ___, singer who won Video of the Year for "Mirrors" at MTV Video Music Awards in 2013 |
| 36% | JANELLEMONAE | 12 | "Dirty Computer" singer who won the GLAAD Media Award for Outstanding Music Artist in 2019: 2 wds. |
| 36% | SAMSMITH | 8 | "Love Goes" singer who won the GLAAD Media Award for Outstanding Music Artist in 2021: 2 wds. |
| 35% | LADYGAGA | 8 | "Born This Way" singer who won the GLAAD Media Award for Outstanding Music Artist in 2012: 2 wds. |
| 35% | GAGA | 4 | Lady ___, singer who won the Video of the Year for "Bad Romance" at MTV Video Music Awards in 2011 |
| 35% | 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.) |
| 35% | OSLIN | 5 | Arkansas-born country singer K.T. ___, who won a Grammy in 1989 for "Hold Me" |
| 35% | KENNYROGERS | 11 | Country Music Hall of Fame singer who's won the American Music Award for Favorite Country Single a record five times (2 wds.) |
| 35% | LUKECOMBS | 9 | 15-Across and 33-Across singer who won the 2019 Country Music Association's New Artist of the Year Award (2 wds.) |
| 35% | MIRANDALAMBERT | 14 | "Tin Man" singer who won Female Vocalist of the Year at the 2018 Academy of Country Music Awards: 2 wds. |
| 35% | CHER | 4 | "Believe" singer who won the Billboard Icon Award in 2017 |
| 35% | 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.) |
| 35% | 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.) |