In 1971, the Academy of Country Music honored Merle Haggard with the first-ever Entertainer of the Year award. Since then, the coveted trophy has been bestowed on some of country music's best and brightest.

Over the years, the ACM Awards have been particularly good to acts such as Alabama, who earned the Entertainer of the Year title five years in a row (1982-1986), and, more recently, Kenny Chesney, who took home the title four times in four years (from 2005 through 2008). Taylor Swift earned two Entertainer of the Year honors before she went pop, and Dolly Parton, Reba McEntire and Loretta Lynn all have one EOTY title to their name ... although the case could certainly be made for more!

George Strait won his first Entertainer of the Year honor 1990 and his second a full 24 years later, in 2014. And then there's Garth Brooks, the artist with the most EOTY wins; he's taken home the title six times, including one year that he couldn't make it in person because his daughter was born the very same day!

Click through the photo gallery below to learn more about every artist who has ever been crowed ACM Entertainer of the Year:

Delayed due to the coronavirus pandemic, the 2020 ACM Awards are set to take place on Sept. 16 at 8PM ET on CBS. This year's ACMs will be broadcast from three venues in Nashville, not Las Vegas, Nev., as in most years. Expect performances from the historic Ryman Auditorium, the iconic Bluebird Cafe and the Grand Ole Opry House, where host Keith Urban will be centered.

The Boot will be staying up late covering the most buzzed-about winners, fashion and moments at the 2020 ACM Awards. Readers can watch along with us by checking back to for the latest CMAs headlines, liking The Boot on Facebook and following The Boot on Twitter.

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