Lainey Wilson pulled off a stunning win at the 2023 CMA Awards when she was crowned Entertainer of the Year. It marked her first time winning in the elite category where few women have won before. Since the CMA Awards premiered in 1967, only eight women have won the Entertainer of the Year: Loretta Lynn, Dolly Parton, Barbara Mandrell, Reba McEntire, Shania Twain, The Chicks, Taylor Swift, and Wilson. Below, we look back at each artist’s win.
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Loretta Lynn
Loretta Lynn is a trailblazer in many ways, including being the first woman to win Entertainer of the Year in 1972. At the time, Lynn had already amassed a decade’s worth of hits with “I’m a Honky Tonk Girl,” “Blue Kentucky Girl,” “You Ain’t Woman Enough (To Take My Man),” and “Don’t Come Home a Drinkin’ (With Lovin’ on Your Mind),” among several others. But her signature hit, “Coal Miner’s Daughter” released in 1970, may have single-handedly handed her the win. The simplicity of the song telling her life story of growing up in the rural town of Butcher Holler, Kentucky, showed the power of poignant storytelling and is now a country standard. But one of the greatest aspects of Lynn’s legacy is her heart. “Loretta Lynn was the first woman in country music to hug me,” Wynonna Judd said backstage at the 2023 CMA Awards. “I remember it like it was yesterday.”
Dolly Parton
After Loretta Lynn, it would be another six years before another woman was crowned, with Dolly Parton earning the title in 1978. In the mid-1970s, Parton had already established herself as a country icon with back-to-back signature tracks “Jolene” and “I Will Always Love You.” By the time she was named Entertainer of the Year for the first time, she’d had nine No. 1 hits on the country charts and released 20 beloved albums. Parton is the entertainer of a lifetime in country music, so the fact that she’s only won Entertainer of the Year once is pretty shocking.
Barbara Mandrell
The ladies led the way in the 1980s, beginning when Barbara Mandrell was crowned Entertainer of the Year two years in a row in 1980 and 1981. Songs like “Sleeping Single in a Double Bed,” “(If Loving You Is Wrong) I Don’t Want to Be Right,” “I Was Country When Country Wasn’t Cool,” and several others made her a mainstay on country radio throughout the 1970s and ’80s. Hosting her own variety show, Barbara Mandrell & the Mandrell Sisters, also made a strong case for Entertainer of the Year status. “The word entertainer means more to me than anything, ” she said during her 1980 acceptance speech, calling country music a “family.” “To be a performer, to feel that in a little bitty way you touch people’s lives and make them and make them happy for the time you spend with them in front of them performing.”
Reba McEntire
Like all the women who came before her, Reba McEntire is a queen of country music. She scored her first Entertainer of the Year win in 1986, the same year she had her first No. 1 album, Whoever’s in New England. The top of the decade is when she really started to pick up steam with hits like “(You Lift Me) Up to Heaven,” “Can’t Even Get the Blues,” and “Whoever’s in New England.” “The entertainment business means the world to me,” McEntire said tearfully in her acceptance speech, adding how when she first got into the business she was told there were many things that “women can’t do.” “Y’all have just proved them wrong,” she said with a smile.
[RELATED: Lainey Wilson Reacts to CMA Awards Wins: “This Ride Just Keeps Getting Wilder”]
Shania Twain
When it comes to entertaining in country music, Shania Twain is unparalleled. When she exploded onto the country scene in the 1990s, she was like a force of nature with hits like “Any Man of Mine,” “That Don’t Impress Me Much,” and “Man! I Feel Like a Woman.” Her live performances were as electrifying as her songs often incorporating choreography into her country-pop jams that resonated with fans all over the world. It was no surprise that she was named Entertainer of the Year in 1999.
The Chicks
One year after Shania Twain’s big Entertainer of the Year win, The Chicks followed in her footsteps in 2000. At the time, the trio of Natalie Maines, Martie Maguire, and Emily Strayer were one of the hottest acts in country music. They had already released five studio albums, with the blockbusters Wide Open Spaces and Fly coming back-to-back in 1998 and 1999. Signature tunes like “There’s Your Trouble,” “Wide Open Spaces,” and “Cowboy Take Me Away” sent them flying up the charts. The Chicks are trailblazers in country music and one of the genre’s most entertaining acts.
Taylor Swift
Taylor Swift made history when she became the youngest CMA Entertainer of the Year winner at just 19 years old. At the time, Swift was well on her way to being a bonafide superstar, having consistently sold out arenas on her Fearless Tour. The album Fearless spawned smash singles like “Love Story,” “You Belong With Me,” and “Fifteen,” which made her a household name. Her impassioned, tear-filled speech where she proclaimed, “I will never forget this moment beacuse in this moment, everything that I have ever wanted just happened to me,” easily made for one of the best CMA Awards moments of all time. She won the award again in 2011, making her and Mandrell the only women to have won Entertainer of the Year twice.
Lainey Wilson
Lainey Wilson continues the legacy of women winning Entertainer of the Year with her groundbreaking 2023 win, marking the second longest gap between female winners (there were 13 years between McEntire and Twain and 12 years between Swift and Wilson). The title was hard-earned for Wilson, who had been hustling in Nashville for more than a decade. She’s spent the bulk of 2023 on the road performing for fans all over the world, in addition to promoting her latest album, Bell Bottom Country, which spawned beloved hits “Heart Like a Truck” and “Watermelon Moonshine.” All of her hard work culminated in that moment when her name was called, comparing the experience to when her parents gave her a wild horse that was up to her to break.
“I tell you what, there were times I was crying and I wanted to get down like let me off the back of this thing but ya’ll every time it would start bucking I held on a little bit tighter, and I think that right there was what prepared me for this ride because it is wild,” she professed in her inspiring acceptance speech. “Thank you for letting me be me.”
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