ACM Entertainer of the Year Award: A History of Women Who've Won

Two years later, the Tennesse darling bested Lynn to pick up what is surprisingly her only entertainer of the year trophy.

Five years after the very first Academy of Country Music Awards, the Coal Miner's Daughter became the first woman to win entertainer of the year. She beat an all-male slate of Glen Campbell, Roy Clark, John Denver and Mickey Gilley.

Mandrell beat Parton and Willie Nelson, among others, in 1981 and according to The Boot, became the first woman to win the Triple Crown Award, having won top new female vocalist in 1972 and top female vocalist in 1979.

A woman wouldn't win again for nearly 15 years as Alabama, Hank Williams Jr. and Garth Brooks dominated the '80s and early '90s. In a poignant speech, Oklahoma native McEntire dedicated her 1995 award to the families of victims of the Oklahoma City Bombings, which had happened just weeks prior.

The year 2000 brought Twain's second entertainer of the year nomination and first win. She was actually out of the country for the awards (she's pictured at right winning a BMI Country Award later in the year), so presenter Dolly Parton accepted on her behalf.

In the first of back-to-back wins for women, the trio (now known as The Chicks) scored their sole entertainer of the year win and the Triple Crown. Band member Martie Maguire accepted the award, shouting out women who paved the way, like previous winner Barbara Mandrell.

Underwood is the female with the most entertainer of the year wins under her belt, at three. Her first was in 2009, when she bested Brad Paisley, George Strait, Keith Urban and Kenny Chesney, and earned the Triple Crown.

She impressively went back-to-back, rising to the top of a packed field that included seven other nominees: Zac Brown Band, Kenny Chesney, Toby Keith, Brad Paisley, George Strait, Taylor Swift and Keith Urban.

In her second year of being nominated, Swift won the award, beating many prior nominees and first-timer Miranda Lambert.

Swift did it again in 2012, and in true Taylor fashion, hugged several of her fellow nominees (and her mom!) on her way to the stage.

In what some considered peak 2020, Underwood tied with Rhett to win the honor at the 55th annual show in Nashville. Host Keith Urban, who presented the award, was shocked as anyone, and when Underwood took her place at the mic, she sighed, "2020, man!" She did, however, congratulate Rhett (who returned the sentiment) and their fellow nominees: Eric Church, Luke Bryan and Luke Combs.