Loretta Lynn, 1972
Since the Country Music Association Awards first aired in 1967, there have only been seven women to win the coveted title of Entertainer of the Year. This year, the category was, once again, male dominated, with host Carrie Underwood as the only female nominated, alongside Garth Brooks, Eric Church, Chris Stapleton and Keith Urban. Brooks won the award, and though he gave a graceful acceptance speech mentioning female singers, Underwood fans were outraged.
The very first woman to trailblaze this category was Lynn in 1972. The star is best known for her hits “You Ain’t Woman Enough (To Take My Man),” “Coal Miner’s Daughter” and a successful career that spans almost 60 years.
Dolly Parton, 1978
Next is the country music legend (and one of this year’s co-hosts), who earned the title in 1978. Dolly is known not only for her impressive discography, but for being a jack of all trades! She is a talented actress, promotes literacy with her organization, Imagination Library, has created her very own theme park, Dollywood, and has been an executive producer in film and television. Parton has an upcoming Netflix series called Heartstrings set to premiere on Nov. 22, 2019.
Barbara Mandrell, 1980 & 1981
Mandrell won back-to-back Entertainer of the Year awards, making her the first woman to win two. Mandrell is known for hits like “Sleeping Single in a Double Bed,” and “I Was Country When Country Wasn’t Cool.” She parlayed her singing career into an acting stint when she earned her own primetime variety show, Barbara Mandrell & the Mandrell Sisters.
Reba McEntire, 1986
Another of this year’s co-hosts, McEntire, won the honor herself in 1986. Like Parton, McEntire has enjoyed a career that crosses mediums. From 42 No. 1 singles to her own long-standing TV show, she is known as the “Queen of Country.”
Shania Twain, 1999
Let’s go girls! The Canadian singer took home the award in 1999, after her third album Come On Over became the best-selling country album in 1997.
With hits like “Man! I Feel Like a Woman,” “You’re Still the One” and “From This Moment On,” Twain solidified herself in country history in that period.
Dixie Chicks, 2000
The only female vocalist group to have won the award, the trio skyrocketed to fame with their debut album, Wide Open Spaces, and continued to dominate the charts with their second album, Fly. In 2000, they were experiencing serious commercial success with both of their albums and were crowned Entertainer(s) of the Year.
After their initial accolades, the group hit a rough patch when they criticized then-president George W. Bush while performing at a concert in England. Many country fans then boycotted their music, causing them to fall from the charts.
The band made a comeback in 2006 with their single “Not Ready to Make Nice,” and album Taking the Long Way Home, and have most recently collaborated with Taylor Swift on the song, “Things Will Get Better” from her new Lover album. They are preparing to release another album in 2020.
Taylor Swift, 2009 & 2011
Another woman who managed to take home the award not once, but twice, Swift has become not only an icon for country music, but an example of how to be a successful crossover artist.
When she won her first award in 2009, she said of the honor, “I will never forget this moment because in this moment, everything I have ever wanted has just happened to me.” The then-19-year-old was fresh off of the success of her second studio album, Fearless.
Two years later, Swift was back to accept her second award, using her arm as a piece of paper to remember all of the people she needed to thank. She was the youngest woman to win the award and the second woman to win it twice.