8 Female Artists Who Have Won The CMA Award For Entertainer Of The Year
on Oct 16, 2025
The 59th Annual CMA Awards Will Take Place On November 19
On November 19, 2025, the Country Music Association Awards will take place at Nashville’s Bridgestone Arena. Hosted by Lainey Wilson, the show will hand out 12 awards throughout the night that always promises star-studded performances.
Usually, the CMA Awards take place earlier in November, but CMA CEO Sarah Trahern revealed they chose a later date as to not conflict with the MLB World Series. Last year’s show was later in November due to the 2024 presidential election.
This year, the ladies are taking over with Ella Langley, Megan Moroney, and Lainey Wilson leading the nominations with six each.
RELATED: See The Complete List Of Nominees For The 2025 CMA Awards
Despite leading the pack in nominations, only one female singer is included in the biggest award of the night: Entertainer of the Year.
Lainey Wilson is up for the award once again alongside Luke Combs, Cody Johnson, Chris Stapleton, and Morgan Wallen.
If Wilson wins Entertainment of the Year, it will be just the 11th time a woman has taken home the award in the show’s 59 years of existence.
Let’s take a look at all the women who have won Entertainer of the Year At The CMA Awards.
Loretta Lynn – 1972
On October 16, 1972, Loretta Lynn became the first woman to take home Entertainer of the Year at the CMA Awards. She also took home Female Vocalist of the Year and Vocal Duo of the Year with Conway Twitty.
The nominees for Entertainer of the Year were: Merle Haggard, Freddie Hart, Charley Pride, and Jerry Reed. It was a stacked category, especially seeing as Haggard and Pride had already take home the award in 1970 and 1971, respectively.
Watch Loretta make history below.
Dolly Parton – 1978
On October 9, 1978, Dolly Parton became the second woman to win Entertainer of the Year at the CMA Awards.
That year, she was also nominated for Album of the Year for Here You Come Again, Female Vocalist of the Year, and Single of the Year for “Here You Come Again.”
The nominees for Entertainer of the Year were: Crystal Gayle, Ronnie Milsap, Kenny Rogers, and Mel Tillis.
Watch Dolly’s acceptance speech below.
Barbara Mandrell – 1980, 1981
On October 13, 1980, Barbara Mandrell co-hosted the 14th CMA Awards with Mac Davis. While she lost out Female Vocalist of the Year to Emmylou Harris, she did become the third woman to win Entertainer of the Year, beating out the Charlie Daniels Band, Larry Gatlin & The Gatlin Brothers, Willie Nelson, and Kenny Rogers.
The following year, she became the first, and only, woman to win Entertainer of the Year in back-to-back years when she took home the award again on October 12, 1981.
That year, she won over Alabama, George Jones, the Oak Ridge Boys, and Kenny Rogers.
Reba McEntire – 1986
The 20th CMA Awards were held on October 13, 1986 and hosted by Willie Nelson and Kris Kristofferson. Reba McEntire and The Judds leds the nominations with five each.
McEntire took home Female Vocalist of the Year before taking home the biggest award of the night, becoming the fourth woman to win Entertainer of the Year at the CMA Awards.
She won Entertainer of the Year over The Judds, Willie Nelson, Ricky Skaggs, and George Strait.
Watch Reba win the award below.
Shania Twain – 1999
Shania Twain became the fifth woman to win Entertainer of the Year at the CMA Awards on September 22, 1999.
It was an especially special moment, seeing as Reba McEntire presented her with the award! Shania took home the award over Garth Brooks, Dixie Chicks, Tim McGraw, and George Strait.
The Chicks (Formerly The Dixie Chicks) – 2000
On October 4, 2000, The Chicks made history by becoming the first all-female group to win Entertainer of the Year at the CMA Awards.
They also took home Vocal Group of the Year, Album of the Year for Fly, and Music Video of the Year for “Goodbye Earl.”
The Chicks, who went by the name Dixie Chicks at the time, beat out Faith Hill, Alan Jackson, Tim McGraw, George Strait.
Taylor Swift – 2009, 2011
On November 11, 2009, Taylor Swift became the youngest person to win Entertainer of the Year at 20 years old. She also took home Album of the Year, Female Vocalist of the Year, and Music Video of the Year for “Love Story.”
She won Entertainer of the Year over some heavy hitters including Kenny Chesney, Brad Paisley, George Strait, and Keith Urban.
In 2011, Swift became just the second woman to win two Entertainer of the Year Awards, taking home the award over Jason Aldean, Brad Paisley, Blake Shelton, and Keith Urban.
It was her lone award of the night.
Lainey Wilson – 2023
Lainey Wilson is the most current woman to take home the Entertainer of the Year trophy when she won on November 8, 2023 at the 58th Annual CMA Awards.
She beat out the likes of Luke Combs, Chris Stapleton, Carrie Underwood, and Morgan Wallen to become the eighth female artist to win the coveted trophy.
Wilson is not only hosting the 2025 show, but she is also nominated for Entertainer of the Year, Album of the Year, Female Vocalist of the Year, Single of the Year, Song of the Year, and Music Video of the Year.
She has a chance to become the third woman in history to win the award twice. Tune in to the 59th Annual CMA Awards on Wednesday, November 19 to find out!
