11 Country Stars Who Shockingly Never Won The CMA’s Entertainer Of The Year Award
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The CMA’s Entertainer of the Year Award is one of the most coveted prizes in country music. But many of the genre’s biggest stars haven’t won it.
Remarkably, in its 60-year history, only 36 artists have ever been named the CMA Entertainer of the Year. That’s because several acts have won multiple times, including Garth Brooks (seven wins), Kenny Chesney (four wins), and George Strait (three wins).
As a result, many fan-favorite country stars have been denied the opportunity to hold the trophy. Scroll through the list below to see 11 singers who’ve shockingly never won the CMA’s Entertainer of the Year award.
Artists Who’ve Never Been Named The CMA Entertainer Of The Year
Toby Keith
The late Toby Keith was known for delivering top-notch performances that kept audiences entertained every second he spent onstage. That’s why country fans find it especially surprising that he never won the CMA’s Entertainer of the Year Award.
Keith was nominated for the award four times between 2002 and 2005. But he lost to Alan Jackson (twice), Kenny Chesney, and Keith Urban.
However, Toby Keith did earn the Entertainer of the Year honor from the rival ACM Awards, taking home the trophy in 2003 and 2004.
Martina McBride
Despite being one of country music’s most beloved female vocalists, Martina McBride has never won the CMA’s Entertainer of the Year Award. But beyond that, she’s never even been nominated.
McBride has won the CMA’s Female Vocalist of the Year honor four times. This makes her continued omission from the EOTY category all the more baffling.
Of the 36 stars who’ve won EOTY, only 8 are female artists (including one group, The Chicks). So, unfortunately, the statistics weren’t on McBride’s side anyway.
Conway Twitty
Conway Twitty remains one of the most influential artists in country music history, inspiring many modern stars such as Scotty McCreery (who recently released a recording of “Hello Darlin’.”)
For two decades, Twitty held the record for the most #1 hits in country music history, with 40 to his name. George Strait eventually surpassed that record.
In other words, Twitty was a popular entertainer in country music. Yet, he never earned the CMA’s Entertainer of the Year Award.
He was nominated for the honor, but only twice, in 1971 and 1975. He lost to Charley Pride and John Denver.
Waylon Jennings
Country fans are appalled when they learn that Waylon Jennings never won the CMA’s Entertainer of the Year award. His exclusion becomes even more mind-boggling when you factor in his inclusion on the first Platinum-certified country album (Wanted! The Outlaws) and his involvement in the iconic supergroup The Highwaymen.
Jennings was nominated in the category three times, from 1975 to 1977. He lost to John Denver, Mel Tillis, and Ronnie Milsap.
George Jones
George Jones‘ impact on the country music community can not be overstated. If you were to ask 100 people to name the greatest artist in the genre’s history, Jones would be one of the most frequently mentioned performers.
He served as the voice behind some of the genre’s most significant songs. “He Stopped Loving Her Today” tops that list, as many have declared that it’s the best country song ever produced.
That’s why fans can’t believe that Jones never won the CMA’s Entertainer of the Year Award. Even more surprising is the fact that he was only nominated in the category once, in 1981. The award was given to Barbara Mandrell that year.
Miranda Lambert
Miranda Lambert holds the record for more wins than any other female artist in CMA history, with 14 to her name. Yet none of those wins were ever for Entertainer of the Year.
Lambert has been nominated for the honor six times, earning her most recent nod in 2022.
Like Toby Keith before her, Lambert has won Entertainer of the Year at the rival ACM Awards. She took home that trophy in 2022.
Chris Stapleton
Chris Stapleton experienced his breakout moment when he sang “Drink You Away” and “Tennessee Whiskey” with Justin Timberlake at the CMA Awards in 2015. He also earned three awards that night: New Artist of the Year, Male Vocalist of the Year, and Album of the Year.
Stapleton has kept the momentum going over the past decade, earning an impressive total of 15 CMA Awards. But the trophy he’s still waiting to add to his collection is the Entertainer of the Year award.
Stapleton has been nominated for EOTY 10 times, including this year (2026). He currently holds the record for the most nominations without a single win.
Kenny Rogers
Kenny Rogers could charm a crowd in an instant with his engaging performances of now-standard songs such as “Lady,” “Islands in the Stream,” and “The Gambler.” Despite this, the CMA never named him their Entertainer of the Year.
Rogers was nominated for the award five times throughout his career, from 1977 to 1981. So although he was recognized with several nods, he never brought home the trophy.
Randy Travis
Many of today’s country artists were influenced by Randy Travis. His unique voice and traditional-leaning songs made him one of the most beloved figures in the industry from the 1980s into the 2010s.
Sadly, Travis suffered a stroke in 2013 that has kept him from singing ever since. He continues to make appearances at industry events, and was inducted into the Country Music Hall of Fame in 2016.
But the CMA’s Entertainer of the Year Award is one honor that Travis has shockingly never earned. He was nominated for it four times, from 1987 to 1990. Hank Williams Jr. won in 1987 and 1988, while George Strait earned the honor in 1989 and 1990.
Travis Tritt
Anyone who’s ever been to a Travis Tritt concert knows the man can put on a show. The energy in the room reaches a fever pitch whenever he bursts into songs such as “Modern Day Bonnie and Clyde” or “T-R-O-U-B-L-E.”
For that reason, we bet you did a double-take when you saw him on this list. But it’s true, Tritt has never won the CMA’s Entertainer of the Year Award.
Even more surprising…he’s only ever been nominated for it once, in 1992. Garth Brooks won that year.
Carrie Underwood
Carrie Underwood‘s name is among the first to come up when people discuss who’s been “snubbed” by the CMA. She hosted the ceremony for 12 years, with that run overlapping with an era when she reigned on the charts and toured extensively.
Underwood’s accomplishments were recognized with six Entertainer of the Year nominations, most recently in 2023. But she never won. (She has been named ACM Entertainer of the Year three times).
As long as her name remains on this list, country fans will consider it a major slight.
Of course, this roundup doesn’t include every artist that has ever been excluded from winning the CMA’s Entertainer of the Year Award. But it does feature some of the most surprising omissions.
If you want to see who has won the category before, head here for our list highlighting all 36 winners. Who do you think deserves it next?
