- - Country Music Hall of Fame singer who's won the American Music Award for Favorite Male Country Artist a record eight times (2 wds.)
- - Country music star honored by the 32-Across with a Lifetime Artistic Achievement Award in 2021 (2 wds.)
- - "The Thunder Rolls" country singer who received a 2020 Kennedy Center Honor: 2 wds.
- - Singer of the 2000 song "Wild Horses": 2 wds.
- - Country singer who has not made his music available on Spotify or iTunes: 2 wds.
- - "The Dance" singer who won the 2016 CMA Award for Entertainer of the Year: 2 wds.
- - Country singer Troyal ....
- - "Friends in Low Places" singer
- - Super Bowl XXVII anthem singer
- - #1 male country singer
- - Country music star who once had the alter ego "Chris Gaines": 2 wds.
- - Country-music superstar
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