The CMA Entertainer of the Year award is the biggest individual honor handed out by the Country Music Association, and for male artists, a nomination itself can be a significant career milestone.
Many of country music’s biggest male stars have won the award over the years, including Garth Brooks, who holds the record with seven wins.
Kenny Chesney has won four times, while George Strait and Alan Jackson have each won three times.
The 2026 CMA Awards will take place Nov. 18 at Nashville’s Bridgestone Arena, with Lainey Wilson hosting the 60th annual ceremony.
While this year’s nominations include plenty of major names, some of country music’s biggest male stars have yet to take home the night’s top prize — and two have never even been nominated for it.
Chris Stapleton
Chris Stapleton has been nominated for CMA Entertainer of the Year 10 times but has never won the category. He’s one of the most decorated artists in CMA history, with 46 total nominations and 19 wins.
Terry Wyatt, Getty ImagesTerry Wyatt, Getty Images
CMA Awards: 46 nominations, 19 wins
Entertainer of the Year: 10 nominations
Jason Aldean
Jason Aldean has received four Entertainer of the Year nominations without winning the award. Overall, Aldean has earned 18 CMA nominations and two wins.
Rick Diamond, Getty ImagesRick Diamond, Getty Images
CMA Awards: 18 nominations, 2 wins
Entertainer of the Year: 4 nominations
Jelly Roll
Jelly Roll has been nominated for CMA Entertainer of the Year once but has yet to win. He has earned eight CMA nominations and one win overall.
Jason Kempin, Getty ImagesJason Kempin, Getty Images
CMA Awards: 8 nominations, 1 win
Entertainer of the Year: 1 nomination
Kane Brown
Kane Brown has never received a CMA Entertainer of the Year nomination. He has four CMA nominations overall but has yet to win a CMA Award.
Jason Kempin, Getty ImagesJason Kempin, Getty Images
CMA Awards: 4 nominations, 0 wins
Entertainer of the Year: 0
Dierks Bentley
Dierks Bentley has also never been nominated for CMA Entertainer of the Year. He’s received 30 CMA nominations throughout his career and has won three times.
Jason Kempin, Getty ImagesJason Kempin, Getty Images
CMA Awards: 30 nominations, 3 wins
Entertainer of the Year: 0
Gallery Credit: Billy Dukes