The artists who’ve won the coveted Entertainer of the Year honor at the ACM Awards over the years are a Who’s Who of the best and brightest in country music history.

Merle Haggard took home the first-ever Entertainer of the Year trophy at the ACM Awards in 1971, right on the heels of a hot streak that included “Okie From Muskogee” and “Fightin’ Side of Me.”

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A number of top county acts have taken home the ACM’s top award multiple times, including  Alabama, who won Entertainer of the Year five years in a row from 1982-1986, and Kenny Chesney, who took top honors four consecutive times from 2005 through 2008.

George Strait took home his first Entertainer of the Year award in 1990, but didn’t score his second until 2014, 24 years later.

Garth Brooks has won the ACM Award for Entertainer of the Year more time than any other artist, a total of six times.

Women have represented country music well in the ACM Awards, too: Taylor Swift has won Entertainer of the Year honors twice, and Dolly Parton, Reba McEntire, Barbara Mandrell and Loretta Lynn have all taken home the ACM’s top honor over the years.

In more recent years, we’ve seen contemporary superstars including Lainey Wilson and Chris Stapleton win Entertainer of the Year at the ACM Awards.

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The category itself has also grown in nominees. In 2023, the Academy debuted a new list that included a whopping seven nominations, rather than the usual five. This appears to be a new trend, as the number of names has remained at seven ever since.

The 2025 nominees for Entertainer of the Year include the reigning winner Wilson, as well as new-to-category star Kelsea Ballerini, Luke Combs, Cody Johnson, Jelly Roll, Chris Stapleton and Morgan Wallen.

The 2025 ACM Awards are set for May 8 and will stream on Amazon Prime Video.

Every ACM Awards Entertainer of the Year Winner Ever