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.”
Who Has Won Entertainer of the Year the Most at the ACM Awards?
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.
Inside the Crazy Secret History of the ACM Awards
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.
READ MORE: Here’s Everything We Know About the 2026 ACM Awards
The 2026 ACM Awards are set to take place in Las Vegas on Sunday, May 17.
Remember: The best way to watch the ACMs is on TV, with ToC on your phone!
