The exclusive list begins with some of the biggest names of the 1970s and incorporates foundational artists from the past 30 years, from '90s country gamechanger Shania Twain to American Idol winner and generational talent Carrie Underwood.
Read on to revisit career-affirming accolades for eight groundbreaking acts.
Loretta Lynn (1975)
Lynn made history in 1971 when she became the first woman nominated for Entertainer of the Year. Four years later, she won the ACM's top prize, joining the same rare air as prior winners Merle Haggard (1970), Freddie Hart (1971), Roy Clark (1972, 1973) and Mac Davis (1974).
She's also the first woman nominee (1971) and winner (1972) of the Country Music Association (CMA) Entertainer of the Year award.
In 1979, the ACM named Lynn its Artist of the Decade for the 1970s. She's the only woman to win a comparable prize, with the other Artist of the Decade honors going to Marty Robbins (1960s), Alabama (1980s), Garth Brooks (1990s), George Strait (2000s) and Jason Aldean (2010s).
Dolly Parton (1977)
The quintessential country music ambassador won the ACM's top prize in her first try. Parton made the final ballot five more times in her illustrious career: 1978, 1980, 1981, 1989 and 1990.
Barbara Mandrell (1980)
Mandrell dominated the television airwaves, award shows included, at the turn of the 1980s. Her momentum at the time positioned her to become the third woman to take home an ACM Entertainer of the Year trophy and the first two-time winner (1980, 1981) of the CMA's top prize.
Reba McEntire (1994)
A decade-plus drought for women as Entertainer of the Year followed Lynn, Parton and Mandrell's shared run of three trophies in six years. McEntire won Entertainer of the Year in a span during which she made the final ballot nine times in 12 years (1986-1997). McEntire's lone CMA Entertainer of the Year victory came in 1986.
Shania Twain (1999)
Twain capped off a decade she helped define by winning Entertainer of the Year from both the CMA and ACM. The Canadian-born country superstar was the first artist born outside of the United States to win either trophy. Her first ACM Entertainer of the Year nomination came the prior year.
The Chicks (2000)
The Chicks rode the momentum of crucial 1999 release Fly to the trio's first and only ACM and CMA Entertainer of the Year wins. Bandmates Natalie Maines, Martie Maguire and Emily Strayer made the ACM's final ballot three times (1999, 2000, 2002) in four years.
The Chicks, Alabama and Brooks & Dunn are the only multi-person groups to win the ACM's top honor.
Carrie Underwood (2009, 2010, 2020)
Underwood made history in 2020 when she shared the evening's top award with Thomas Rhett. She joined Alabama, Hank Williams Jr., Garth Brooks, Brooks & Dunn, Kenny Chesney, Jason Aldean and Luke Bryan as the only acts to win Entertainer of the Year three or more times.
Taylor Swift (2011, 2012)
Before conquering pop music, Swift's ace lyricism and star power earned her consecutive Entertainer of the Year honors by age 22. Indeed, she was the youngest artist to win the ACM and CMA's top awards (she's won both twice, earning the CMA's most coveted prize in 2009 and 2011).
Miranda Lambert (2022)
A decade-long drought for women ended in 2022 when the most decorated artist in ACM history donned her rightful crown as Entertainer of the Year.
Lambert accepted the award via video from London, days before a headlining appearance at the Country 2 Country festival.
"This is my first time missing the ACMs in 17 years," she said during the broadcast. "My heart is a little broken, but I'm happy to be where I am. I've been waiting for this for a really, really long time. I actually never thought it would happen. But thank you so much to the country music family for embracing me all these years and continuing to support me."
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