Entertainment Music Country 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 was the Features Editor of PEOPLE Digital from 2019 to 2022. She worked at the brand for nearly four years covering news, features, human interest, evergreen, holiday gift guides and more. She launched the How I Parent and What It's Really Like to Be …. digital series and has interviewed several celebrities and influential leaders within the entertainment industry. Prior to joining PEOPLE, Diane worked at Bustle, VH1 and Complex. She received her bachelor's degree in Journalism from Rutgers University and her master's degree from Columbia Journalism School. People Editorial Guidelines and Andrea Wurzburger Updated on November 9, 2022 02:20 PM Share Tweet Pin Email Trending Videos 01 of 07 Loretta Lynn, 1972 Eric Ogden 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 is, once again, male dominated, with Carrie Underwood and Miranda Lambert the only females nominated, alongside Luke Combs, Chris Stapleton and Morgan Wallen. 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 07 Dolly Parton, 1978 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 07 Barbara Mandrell, 1980 & 1981 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 07 Reba McEntire, 1986 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 07 Shania Twain, 1999 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 07 Dixie Chicks, 2000 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 07 Taylor Swift, 2009 & 2011 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.