From Merle Haggard to Miranda Lambert, All the ACM Award Winners for Entertainer of the Year

Who will win entertainer of the year at the 58th annual Academy of Country Music Awards on May 11?

Miranda Lambert could win for the second year in a row, which would make her only the third woman to win more than once in this category, following Carrie Underwood and Taylor Swift.

Either Underwood or Jason Aldean could take it for the fourth time, a total reached by only three acts in ACM history – Garth Brooks, who leads with six awards; Alabama, which is second with five wins; and Kenny Chesney, who has won four times. If Underwood wins, she would extend her lead as the woman with the most wins in the category.

Or we could see a first-time winner.

Kane Brown could make history as the first Black or biracial entertainer of the year winner. (Charley Pride won entertainer of the year at the CMA Awards, but not here, despite three nominations.) Either Brown or Morgan Wallen would also be the first male artist to win before turning 30 since Brooks in 1991. (Wallen hits the Big 3-0 two days after the ceremony.) A win for Wallen would cap a fast comeback from the career crisis caused by his videotaped use of a racial slur in early 2021.

Luke Combs, who has won the CMA award for entertainer of the year the last two years, could finally win the top prize at this show. Chris Stapleton, a three-time ACM winner for male artist of the year, could finally win entertainer of the year on his fifth try in the category.

The show will be hosted by two former entertainer of the year winners – Dolly Parton (who in 1978 became the second woman to win the award) and Brooks. It will be held at Ford Center at The Star in Frisco, Tex. and will stream on Amazon Prime.

Twenty-seven artists have won the ACM Award for entertainer of the year since the award was introduced on the 1971 telecast. Here’s a complete list, showing the year(s) in which they won, other ACM Awards they won that year in competitive categories (if any), their total number of ACM entertainer of the year nominations; and, just for fun, their highest-charting hit on the Billboard Hot 100.