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The artists who’ve won the coveted Entertainer of the Year honor at the ACM Awards<\/a> over the years are a Who’s Who of the best and brightest in country music history.<\/p>\n Merle Haggard<\/a>\u00a0took home the first-ever Entertainer of the Year trophy\u00a0at the ACM Awards in 1971, right on the heels of a hot streak that included “Okie From Muskogee” and “Fightin’ Side of Me.”<\/p>\n A number of top county acts have taken home the ACM’s top award multiple times, including\u00a0\u00a0Alabama<\/a>, who won Entertainer of the Year five years in a row from 1982-1986, and\u00a0Kenny Chesney,<\/a>\u00a0who took top honors four consecutive times from 2005 through 2008.<\/p>\n George Strait<\/a>\u00a0took home his first Entertainer of the Year award in 1990,\u00a0but\u00a0didn’t score his second until 2014, 24 years later.<\/p>\n Garth Brooks\u00a0<\/a>has won the ACM Award for Entertainer of the Year more time than any other artist, a total of six times.<\/p>\n Women have represented country music well in the ACM Awards, too.<\/p>\n Taylor Swift<\/a>\u00a0has won Entertainer of the Year honors twice, and\u00a0Dolly Parton<\/a>, Reba McEntire<\/a>,\u00a0Barbara Mandrell\u00a0and Loretta Lynn<\/a>\u00a0have all taken home the ACM’s top honor over the years.<\/p>\n In more recent years, we’ve seen contemporary superstars including Lainey Wilson<\/a> and Chris Stapleton<\/a>\u00a0win Entertainer of the Year at the ACM Awards.<\/p>\n Inside the Crazy Secret History of the ACM Awards<\/strong><\/p>\n 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.<\/p>\nWho Has Won Entertainer of the Year the Most at the ACM Awards?<\/h3>\n