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5 Male Country Singers Without a CMA Entertainer of the Year Win


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.

Read More: 5 Female Country Superstars Who Haven’t Won CMA Entertainer of the Year – 2 Have Never Been Nominated

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 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 Images
Rick 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 Images
Jason 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 Images
Jason 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 Images
Jason Kempin, Getty Images

CMA Awards: 30 nominations, 3 wins
Entertainer of the Year: 0

2026 CMA Awards Nominations – Snubs + Surprises Reveal a Dangerous Trend

This isn’t the year for fans of traditional country music to complain. Anyone who does it like Alan, and George was rewarded while those who pushed the boundaries of the genre were forgotten. Here are seven snubs and two surprises from the 2026 CMA Awards nominations list.

Gallery Credit: Billy Dukes





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Graham Haring

Graham Haring is a versatile writer with a knack for capturing the heart of country music and the stories that surround it. Covering everything from new song releases by icons like Tim McGraw to unexpected cultural phenomena like "The Waffle House Index," his articles bring a mix of humor, depth, and curiosity to the table. Graham’s work often explores the personal side of country music, highlighting the community, family moments, and heartwarming stories behind the headlines. Whether it’s about Keith Urban's benefit shows or a quirky note from the past, Graham's writing resonates with country fans who appreciate a touch of authenticity and a good story.

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