Entertainment Awards Shows and Events All of the Women Who've Won the CMA Entertainer of the Year Award These legendary stars earned their top spot in the historically male-dominated category By Diane J. Cho Diane J. Cho Diane J. Cho is the former features editor of PEOPLE, covering news, features, human interest and more. She left PEOPLE in 2022 People Editorial Guidelines and Andrea Wurzburger Andrea Wurzburger Andrea Wurzburger is a former features writer at PEOPLE. She left PEOPLE in 2022. People Editorial Guidelines Updated on November 8, 2023 11:13PM EST Dolly Parton and Taylor Swift. Photo: Chelsea Lauren/Shutterstock; ANGELA WEISS/AFP via Getty Since the Country Music Association Awards first aired in 1967, there have only been eight women to win the coveted title of Entertainer of the Year. This year, the category was once again male dominated, with Carrie Underwood and Lainey Wilson the only females nominated, alongside Luke Combs, Chris Stapleton and Morgan Wallen. In an exciting moment, Wilson — the night's top nominee, with nine nods — won, making her the first woman to do so since Taylor Swift scored her second title in 2011. Here, a look at the women who went before her. 01 of 08 Loretta Lynn, 1972 Loretta Lynn. Eric Ogden The very first woman to trailblaze this category was Loretta Lynn in 1972. The late 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 spanned almost 60 years. 02 of 08 Dolly Parton, 1978 Dolly Parton. Dave J Hogan/Dave J Hogan/Getty Images Next is the country music legend Dolly Parton, who earned the title in 1978. Parton 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. She was also inducted into the Rock & Roll Hall of Fame in November 2022. 03 of 08 Barbara Mandrell, 1980 & 1981 Barbara Mandrell. Jon Kopaloff/FilmMagic Barbara 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. 04 of 08 Reba McEntire, 1986 Reba McEntire. Ron Wolfson/WireImage Reba McEntire won the honor 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." 05 of 08 Shania Twain, 1999 Shania Twain. Samir Hussein/WireImage Let's go girls! Canadian singer Shania Twain 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. 06 of 08 Dixie Chicks, 2000 The Chicks. Christie Goodwin/Getty Images The only female vocalist group to have won the award, the Dixie Chicks 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 more recently collaborated with Taylor Swift on the song, "Things Will Get Better" from her Lover album. In 2020 they dropped the "Dixie" in their name and released another album, Gaslighter, as the Chicks. 07 of 08 Taylor Swift, 2009 & 2011 Taylor Swift. Sara Kauss/Getty Images Another woman who managed to take home the award not once, but twice, Taylor 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. 08 of 08 Lainey Wilson, 2023 Lainey Wilson. Terry Wyatt/Getty Breaking a long streak of men's wins, Lainey Wilson took home the award in 2023. "This is all I've ever wanted to do," she said in her tearful acceptance speech. "It's the only thing I know how to do. I've been in this town for twelve-and-a-half years and it finally feels like country music is starting to love me back. I love it with my whole heart." Close