All the CMA Awards Winners for Entertainer of the Year Who Have Won Multiple Times

When the award for entertainer of the year is presented at the 58th annual CMA Awards on Thursday Nov. 20, we could see history being made. If Lainey Wilson wins for the second year in a row, she’ll become just the second woman to win two years running. Barbara Mandrell was the first, in 1980 and 1981.

If Jelly Roll wins, this will be the second year in a row that a relative newcomer has swooped in and won entertainer of the year the first time they were nominated. Wilson achieved the feat last year. Not since the 1970s have we seen first-time entertainer of the year nominees win the award in back-to-back years. Back then, it happened four years in a row with Roy Clark (1973), Charlie Rich (1974), John Denver (1975) and Mel Tillis (1976).

If Chris Stapleton wins at long last on his eighth nomination in the category, he will cease to be the artist with the most nominations in the category without a win. (That distinction would then be held by Carrie Underwood, who is 0-6 in the category.)

The other two nominees in the category are Luke Combs, who is vying for his third win in the category inside of four years, and Morgan Wallen, who is nominated for the third year in a row. He has yet to win.

According to the CMA site, the CMA Award for entertainer of the year “is for the act displaying the greatest competence in all aspects of the entertainment field. Voter should give consideration not only to recorded performance, but also to the in-person performance, public acceptance, leadership, and overall contribution to Country Music.”

The inaugural recipient of the award was Eddy Arnold in 1967. In 1971, Charley Pride became the first (and still only) person of color to win the award. The following year, Loretta Lynn became the first woman to win. In 1982, Alabama being the first group to take the prize. In 1996, Brooks & Dunn became the first (and still only) duo to win.

Here all the artists who have won the CMA award for entertainer of the year multiple times.