LIST: 36 Artists Have Won CMA Entertainer Of The Year — Who Will Be Next?
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Being named CMA Entertainer of the Year is something that many country artists dream about, but only a few have ever experienced. Known as the CMA’s most prestigious honor, the award has been bestowed every year since 1967.
According to the CMA’s website, the Entertainer of the Year award is given to:
“…the act displaying the greatest competence in all aspects of the entertainment field. Voter[s] should give consideration not only to recorded performance, but also to the in-person performance, public acceptance, leadership, and overall contribution to Country Music.”
A new CMA Entertainer of the Year will be crowned on Wednesday, November 18. This year’s nominees are Lainey Wilson, Cody Johnson, Chris Stapleton, Luke Combs, and Ella Langley.
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Who do you think will win? Regardless of who it will be, we know that whoever takes home the trophy this year will follow in the footsteps of some truly remarkable performers.
Scroll through the list below to see every artist who’s been named CMA Entertainer of the Year so far, and learn why certain wins are extra noteworthy in the grand scheme of CMA history.
Just a note, this list is mostly chronological, with a few exceptions. If an artist won in multiple years (such as Lainey Wilson in 2023 and 2025), we’ve grouped their wins together in one entry. That’s why you may see some “gaps” in the timeline…but trust us, all of the winners have been accounted for!
Every CMA Entertainer Of The Year – From 1967 To 2025
Eddy Arnold (1 Win -1967)
Eddy Arnold was the first artist to ever win the CMA’s Entertainer of the Year Award. The “Lonely Again” singer had been nominated against Bill Anderson, Merle Haggard, Sonny James, and Buck Owens.
Glen Campbell (1 Win – 1968)
After being nominated in the category the previous year, Glen Campbell was named the CMA’s Entertainer of the Year for 1968. His win came following the release of hits such as “I Wanna Live” and “By the Time I Get to Phoenix.”
The other artists nominated for the award in 1968 were 1967’s winner Eddy Arnold, Johnny Cash, Merle Haggard, and Charley Pride.
Johnny Cash (1 Win – 1969)
Just one year after earning his first Entertainer of the Year nomination, Johnny Cash secured his first (and surprisingly, only) win. This came following the success of “Daddy Sang Bass,” “A Boy Named Sue,” and a live version of “Folsom Prison Blues,” with the latter two songs listed as tracks on his now-iconic album, At San Quentin.
Cash had been nominated against then-reigning winner Glen Campbell, in addition to Roy Clark, Merle Haggard, and Charley Pride.
Merle Haggard (1 Win – 1970)
Merle Haggard was nominated for the CMA’s Entertainer of the Year Award three times before he finally won. He took home the trophy in 1970, the same year he released “The Fightin’ Side of Me,” “Jesus, Take a Hold,” and “I Can’t Be Myself.”
Haggard’s fellow nominees in 1970 were previous winners Johnny Cash and Glen Campbell, as well as Roy Clark and Charley Pride.
Charley Pride (1 Win – 1971)
Country music history was made with the naming of the CMA Entertainer of the Year in 1971. After three prior nominations, Charley Pride became the first Black artist to win the category.
Charley’s win came following the release of his hit singles “I’d Rather Love You” and “I’m Just Me.” He dropped what became his signature song, “Kiss An Angel Good Mornin’,” only 13 days after the CMA Awards ceremony.
The other Entertainer of the Year nominees in 1971 were Merle Haggard, Loretta Lynn, Jerry Reed, and Conway Twitty.
Loretta Lynn (1 Win – 1972)
Just one year after she was the first female artist to be nominated for Entertainer of the Year, Loretta Lynn became the first female artist to win it. Her victory came after she reigned over the charts with singles such as “One’s On the Way,” “Here I Am Again,” and “Lead Me On” (a duet with Conway Twitty).
Merle Haggard, Freddie Hart, Charley Pride, and Jerry Reed were the other nominees in the category that year.
Roy Clark (1 Win – 1973)
Roy Clark had been nominated for the CMA Entertainer of the Year award twice before he earned his first and only win in 1973. The Hee Haw star had been on a roll that year, thanks in large part to his chart-topping hit “Come Live With Me.”
The other nominees in the category that year were Merle Haggard, Tom T. Hall, Loretta Lynn, and Charley Pride.
Charlie Rich (1 Win – 1974)
Charlie Rich was crowned the CMA’s Entertainer of the Year in 1974. The honor was bestowed upon Rich after a wildly successful string of #1 hits, including “The Most Beautiful Girl,” “There Won’t Be Anymore,” “A Very Special Love Song,” “I Don’t See Me in Your Eyes Anymore,” and “I Love My Friend.”
Rich was nominated against prior winners Roy Clark and Loretta Lynn, as well as first-time nominees Olivia Newton-John and Mac Davis.
John Denver (1 Win – 1975)
John Denver‘s 1975 Entertainer of the Year win may be one of the most memorable in CMA history. That was the same year he released “Thank God I’m a Country Boy,” but that’s not the reason why people remember his victory.
The previous year’s winner, Charlie Rich, introduced the nominees: Denver, Waylon Jennings, Loretta Lynn, Ronnie Milsap, and Conway Twitty. Then, as he opened the envelope and read the name on the slip, he set the paper on fire before naming Denver as the winner.
Denver, who couldn’t attend the ceremony, accepted his award via satellite. History.com reports that because of this, he had no clue what Rich had done.
Some believed Rich did this in protest of Denver’s win, since he wasn’t a purely traditional country artist. History.com reports that Rich later admitted to being under the influence of prescription pain medication and alcohol that evening, and quotes his son, Charlie Rich Jr., as saying:
“He used bad judgment. He was human after all. I know the last thing my father would have wanted to do was set himself up as judge of another musician.”
Mel Tillis (1 Win – 1976)
The legendary Mel Tillis earned his first and only Entertainer of the Year trophy from the CMA in 1976.
The win came after Tillis dominated the charts with hits such as “Mental Revenge” and “Love Revival.” Just one month before the CMA Awards on October 11, he released one of the biggest hits of his career, the #1 song “Good Woman Blues.”
Other nominees that year were Waylon Jennings, Ronnie Milsap, Willie Nelson, and Dolly Parton.
Ronnie Milsap (1 Win – 1977)
After two prior nominations, Ronnie Milsap finally brought home the CMA’s Entertainer of the Year award in 1977. The win was the perfect bookend to a year that included the release of multiple #1 singles: “(I’m A) Stand by My Woman Man,” “Let My Love Be Your Pillow,” and “It Was Almost Like a Song.”
Milsap was nominated against Merle Haggard, Waylon Jennings, Dolly Parton, and Kenny Rogers that year.
Dolly Parton (1 Win – 1978)
In 1978, Dolly Parton became the second woman to ever be named the CMA Entertainer of the Year. Her win followed the release of crossover hits such as “Here You Come Again” and “Two Doors Down,” as well as the chart-topping country song “It’s All Wrong, But It’s All Right.”
She was nominated against prior winners Ronnie Milsap and Mel Tillis, her future duet partner Kenny Rogers, and first-time nominee Crystal Gayle.
Willie Nelson (1 Win – 1979)
Can you believe that Willie Nelson has only won the Entertainer of the Year Award once? That win came in 1979, the same year that Nelson released his Sweet Memories album, the single “September Song,” and a live recording of “Whiskey River.”
Nelson’s fellow nominees that year were Crystal Gayle, Barbara Mandrell, Kenny Rogers, and the Statler Brothers.
Barbara Mandrell (2 Wins – 1980 & 1981)
Few country stars have ever had the same hold on fans as Barbara Mandrell in the ’80s. She was an unstoppable force, scoring hits such as “Crackers,” “The Best of Strangers,” “Years,” and her future signature song, “I Was Country When Country Wasn’t Cool,” in the decade’s first two years.
Her success led to her first Entertainer of the Year win in 1980, followed by another in 1981. She made history not only as the first artist to win the category twice, but to win it in two consecutive years. Additionally, Mandrell and Mac Davis co-hosted the CMA Awards ceremony both years.
In 1980, Mandrell had been nominated against the Charlie Daniels Band
Larry Gatlin & The Gatlin Brothers, then-reigning winner Willie Nelson, and Kenny Rogers. The other nominees in 1981 were Alabama, George Jones, the Oak Ridge Boys, and Kenny Rogers.
Alabama (3 Wins – 1982, 1983, & 1984)
The ’80s were some major history-making years for artists at the CMA Awards. Alabama became the first group to win the Entertainer of the Year Award in 1982, before going on to win it again in 1983 and 1984.
They were the first artist to win the award three times, and also the first to win it in three consecutive years. Those were the years that they released their now-timeless hits such as “Mountain Music,” “Dixieland Delight,” “The Closer You Get,” and “Roll On (Eighteen Wheeler).”
These are the artists who were nominated against them in each of those years:
- 1982 – Barbara Mandrell, Willie Nelson, the Oak Ridge Boys, and Ricky Skaggs
- 1983 – Merle Haggard, Barbara Mandrell, Willie Nelson, and Ricky Skaggs
- 1984 – Lee Greenwood, Barbara Mandrell, Ronnie Milsap, and the Oak Ridge Boys
Ricky Skaggs (1 Win – 1985)
After two prior nominations, Ricky Skaggs won his first and only CMA Entertainer of the Year award in 1985. That was the same year he released his #1 single “Country Boy” and the Top 10 hit “You Make Me Feel Like a Man.”
The other artists nominated in the category that year were Alabama, Lee Greenwood, Reba McEntire, and George Strait.
Reba McEntire (1 Win – 1986)
Considering her superstar status, it’s surprising that Reba McEntire has only won the CMA’s Entertainer of the Year award once. That win came in 1986, the same year she released “Whoever’s In New England,” “Little Rock,” and “What Am I Gonna Do About You.”
The other artists who were nominated against McEntire that year were The Judds, Willie Nelson, Ricky Skaggs, and George Strait.
Hank Williams Jr. (2 Wins – 1987 & 1988)
Hank Williams Jr. was named the Entertainer of the Year in back-to-back years, 1987 and 1988. Those wins could surely be attributed to the success of his hit singles “Born to Boogie,” “Heaven Can’t Be Found,” and “If the South Woulda Won,” among others.
Williams was up against The Judds, Reba McEntire, George Strait, and Randy Travis in 1987. He defended his title against The Judds, Reba McEntire, George Strait, and Randy Travis in 1988.
George Strait (3 Wins – 1989, 1990, & 2013)
It only seems right that “The King of Country,” George Strait, has been awarded the CMA’s Entertainer of the Year award three times.
His first two wins came in 1989 and 1990, the same years he released chart-topping hits such as “Ace in the Hole” and “Love Without End, Amen.” 23 years passed before Strait won the award a third time…which is the longest-ever break between wins in the category’s history.
These are the other artists Strait was up against in the years that he won:
- 1989 – Reba McEntire, Randy Travis, Ricky Van Shelton, and Hank Williams, Jr.
- 1990 – Clint Black, Kathy Mattea, Ricky Van Shelton, and Randy Travis
- 2013 – Jason Aldean, Luke Bryan, Blake Shelton, and Taylor Swift
Garth Brooks (7 Wins – 1991, 1992, 1997, 1998, 2016, 2017, & 2019)
As one of country music’s most well-known entertainers, it makes sense that the CMA has honored Garth Brooks with the Entertainer of the Year Award not once, not twice, but SEVEN times.
He earned back-to-back wins in 1991 and 1992, followed by another set of consecutive wins in 1997 and 1998. He earned his next win 18 years later in 2016, followed by two more in 2017 and 2019. His seven wins make him the most-awarded artist in the category’s history.
Here’s the list of the other artists who were nominated against Brooks during the above-mentioned years:
- 1991 – Clint Black, Vince Gill, Reba McEntire, and George Strait
- 1992 – Vince Gill, Alan Jackson, Reba McEntire, and Travis Tritt
- 1997 – Brooks & Dunn, Vince Gill, Alan Jackson, and George Strait
- 1998 – Brooks & Dunn, Vince Gill, Tim McGraw, and George Strait
- 2016 – Luke Bryan, Chris Stapleton, Carrie Underwood, and Keith Urban
- 2017 – Luke Bryan, Eric Church, Chris Stapleton, and Keith Urban
- 2019 – Eric Church, Chris Stapleton, Carrie Underwood, and Keith Urban
Vince Gill (2 Wins – 1993 & 1994)
After Garth Brooks’ first string of Entertainer of the Year wins, Vince Gill swooped in to claim the category in 1993 and 1994. Those were the years that Gill released hits such as “One More Last Chance,” “Tryin’ to Get Over You,” and “Whenever You Come Around.”
Gill had been nominated against Brooks & Dunn, then-reigning winner Garth Brooks, Alan Jackson, and Reba McEntire in 1993. His fellow nominees in 1994 were Brooks & Dunn, Garth Brooks, Alan Jackson, and Reba McEntire.
Alan Jackson (3 Wins – 1995, 2002, & 2003)
The CMA Entertainer of the Year in 1995 was the one and only Alan Jackson. That win followed the success of singles such as “Gone Country” and “Tall, Tall Trees.”
Seven years after his first win, Jackson took the category again in 2002, followed by another win in 2003. Those wins occurred after the release of singles such as “Where Were You (When the World Stopped Turning),” “Drive,” and “It’s Five O’Clock Somewhere.”
Here’s a look at the artists who were nominated against Jackson in the years that he won:
- 1995 – Brooks & Dunn, Garth Brooks, Vince Gill, and Reba McEntire
- 2002 – Brooks & Dunn, Kenny Chesney, Toby Keith, and George Strait
- 2003 – Brooks & Dunn, Kenny Chesney, Toby Keith, and Tim McGraw
Brooks & Dunn (1 Win – 1996)
Brooks & Dunn made CMA history in 1996 by becoming the first (and so far, only) duo to win Entertainer of the Year. The victory came in the same year that the pair released “My Maria,” “I Am That Man,” and their famous Borderline album.
The other artists who were up for Entertainer of the Year in 1996 were Garth Brooks, Vince Gill, Alan Jackson, and George Strait.
Shania Twain (1 Win – 1999)
Shania Twain closed out the ’90s by winning the CMA’s Entertainer of the Year award in 1999. That win came following the success of her now-iconic songs “That Don’t Impress Me Much,” “Man! I Feel Like a Woman,” and “You’ve Got a Way.”
Twain was up against Garth Brooks, The Chicks, Tim McGraw, and George Strait that year.
The Chicks (1 Win – 2000)
18 years after Alabama became the first group to be named the Entertainer of the Year, The Chicks became the first all-female group to win the category. Their win arrived following the mid-1999 release of their #1 album Fly, which produced the hit singles “Ready to Run,” “Cowboy Take Me Away,” and “Goodbye Earl.”
Other nominees for Entertainer of the Year in 2000 were Faith Hill, Alan Jackson, Tim McGraw, and George Strait.
Tim McGraw (1 Win – 2001)
Tim McGraw was one of country music’s leading stars during the early 2000s. That was made clear when he took home his first (and only) Entertainer of the Year award in 2001.
McGraw’s win came the same year that he reigned over the charts with #1 hits “My Next Thirty Years,” “Grown Men Don’t Cry,” and “Angry All The Time.”
McGraw was nominated against a group of former winners, including Brooks & Dunn, The Chicks, Alan Jackson, and George Strait.
Kenny Chesney (4 Wins – 2004, 2006, 2007, & 2008)
Kenny Chesney claimed his first Entertainer of the Year win in 2004, the same year he released “When the Sun Goes Down” and “I Go Back.”
He didn’t win in 2005, but reclaimed his title in 2006, followed by two more wins in 2007 and 2008. Other than Alabama, he’s the only artist to win the category in three consecutive years.
Kenny’s four wins make him the second-most awarded artist in the category, with only Garth Brooks ranking above him (with seven wins).
Look below to see all of the other artists that were nominated in the years Chesney won:
- 2004 – Brooks & Dunn, Alan Jackson, Toby Keith, and Tim McGraw
- 2006 – Brooks & Dunn, Brad Paisley, Rascal Flatts, and Keith Urban
- 2007 – Brad Paisley, Rascal Flatts, George Strait, and Keith Urban
- 2008 – Brad Paisley, George Strait, Sugarland, and Keith Urban
Keith Urban (2 Wins – 2005 & 2018)
In between Kenny Chesney’s run of wins, Keith Urban claimed the Entertainer of the Year award in 2005. That was the same year he released the #1 singles “Better Life” and “Making Memories Of Us.”
The other artists nominated for the award in 2005 were Kenny Chesney, Alan Jackson, Toby Keith, and Brad Paisley.
13 years after his first win, Urban claimed the category again in 2018. His fellow nominees that year were Jason Aldean, Luke Bryan, Kenny Chesney, and Chris Stapleton.
Taylor Swift (2 Wins – 2009 & 2011)
Taylor Swift closed out the 2000s by winning the CMA’s Entertainer of the Year award in 2009. The win followed the 2008 release of her Fearless album, which produced the hit singles “Love Story,” “White Horse,” “You Belong With Me,” and “Fifteen.”
Swift was only 19 at the time, making her the youngest person to ever win the category. She was nominated against Kenny Chesney, Brad Paisley, George Strait, and Keith Urban.
She didn’t win in 2010, but made a comeback to claim the trophy in 2011. That victory followed the release of her third album, Speak Now, which contained the hit singles “Today Was a Fairytale,” “Mine,” “Back To December,” “Mean,” and “The Story of Us.”
The other artists nominated for Entertainer of the Year in 2011 were Jason Aldean, Brad Paisley, Blake Shelton, and Keith Urban.
Brad Paisley (1 Win – 2010)
In between Taylor Swift’s wins, Brad Paisley was named the Entertainer of the Year in 2010. His win came after the success of several singles, including “American Saturday Night,” “Water,” and “Anything But Mine.”
Other Entertainer of the Year nominees in 2010 were Lady A, Miranda Lambert, Keith Urban, and the Zac Brown Band.
Paisley also co-hosted that year’s CMA Awards with Carrie Underwood. It was their third time hosting the ceremony, and they remained the hosts through 2018.
Blake Shelton (1 Win – 2012)
Can you believe that Blake Shelton has only been named the CMA Entertainer of the Year once?
His win came in 2012, the same year he released “Drink On It” and “Over,” and one year after he made his debut as a coach on The Voice. The show was in the middle of its third season at that point (which Shelton eventually won with Cassadee Pope).
The other artists nominated for Entertainer of the Year in 2012 were Jason Aldean, Kenny Chesney, Brad Paisley, and Taylor Swift.
Luke Bryan (2 Wins – 2014 & 2015)
Luke Bryan scored a pair of back-to-back wins, being named the Entertainer of the Year in 2014 and 2015. Those were the years that he released the #1 hits “Play It Again,” “I See You,” “Strip It Down,” and “Kick the Dust Up.”
Bryan was up against Miranda Lambert, Blake Shelton, then-reigning winner George Strait, and Keith Urban in 2014. In 2015, he defended his title against Garth Brooks, Miranda Lambert, Eric Church, and Kenny Chesney.
Eric Church (1 Win – 2020)
After three Garth Brooks wins and a Keith Urban victory in the middle, Eric Church became the first country artist to win the Entertainer of the Year award in the 2020s.
In a year when live performances were understandably scarce, Church remained one of the strongest voices in the industry. That can be attributed to the success of his singles “Monsters” and “Stick That in Your Country Song.”
Church was nominated against Luke Combs, Miranda Lambert, Carrie Underwood, and Keith Urban that year.
Luke Combs (2 Wins – 2021 & 2022)
Luke Combs is known for being a powerhouse onstage, and his talent was rewarded with back-to-back Entertainer of the Year trophies in 2021 and 2022.
Over those years, Combs released his hit album Growin’ Up and the smash singles “Forever After All,” “Cold As You,” “The Kind of Love We Make,” and “Going, Going, Gone.”
Combs beat then-reigning winner Eric Church, Miranda Lambert, Chris Stapleton, and Carrie Underwood to win in 2021. He defended his title against Miranda Lambert, Chris Stapleton, Carrie Underwood, and Morgan Wallen in 2022.
Lainey Wilson (2 Wins – 2023 & 2025)
Lainey Wilson won her first Entertainer of the Year award in 2023. That was the same year that “Heart Like a Truck” hit #1, and she dropped “Watermelon Moonshine” (which also topped the chart). Both songs came from her highly regarded album, Bell-Bottom Country, which she released near the end of 2022.
Wilson had been nominated against Luke Combs, Chris Stapleton, Morgan Wallen, and Carrie Underwood in 2023.
Wilson returned to reclaim her title in 2025, the same year she hosted the ceremony solo for the first time. It was also the year she released her chart-topping hit “Somewhere Over Laredo.”
The other artists nominated in 2025 were Luke Combs, Cody Johnson, Chris Stapleton, and Morgan Wallen.
Morgan Wallen (1 Win – 2024)
Given his star power, many fans are surprised to learn that Morgan Wallen has won the CMA’s Entertainer of the Year Award only once. That win arrived in 2024, the same year he released “Cowgirls,” “Lies Lies Lies,” and “Love Somebody.”
The other nominees that year were Luke Combs, Jelly Roll, Chris Stapleton, and Lainey Wilson. Wallen did not attend the ceremony, so presenter Jeff Bridges accepted the award on his behalf.
Who Will Be Named The CMA Entertainer Of The Year In 2026?
As mentioned previously, Lainey Wilson, Luke Combs, Chris Stapleton, Cody Johnson, and Ella Langley are the 2026 nominees for Entertainer of the Year.
Will Wilson defend her title and become the first female artist to win the award three times? Or will Combs step in to claim the award again after a four-year break?
Then you have Stapleton, Johnson, and Langley, who all stand the chance to earn their first win in the category this year. Tune in to the CMA Awards on November 18th to see if they do!
