Youngest country music “Entertainer of the Year”
Taylor Swift
19:333 year(s):day(s)
United States ()

Taylor Swift (USA, b. 13 December 1989) is the youngest winner of Entertainer of the Year at both the Country Music Association (CMA) and the Academy of Country Music (ACM) Awards. She took home the prize at the 43rd and 45th editions of the CMA Awards, respectively on 11 November 2009 and 9 November 2011 – formerly when she was 19 years 333 days old. At the ACM Awards, Swift won Entertainer of the Year two years in a row, in 2011–12. She was 21 years 111 days old on the date of the 3 April 2011 ceremony.

Carrie Underwood (USA, b. 10 March 1983) won Entertainer of the Year at the ACM Awards in 2009–10 and 2020. The 44th ACM Awards were held on 5 April 2009, when she was 26 years 26 days old. Underwood is a five-time Entertainer of the Year nominee at the CMA Awards (2016 and 2019–22).

Multiple Entertainer of the Year winners include: Garth Brooks (7 CMA, 6 ACM), Kenny Chesney (4 CMA, 5 ACM), Alan Jackson (3 CMA), George Strait (3 CMA, 2 ACM), Alabama (3 CMA, 5 ACM), Hank Williams Jr (2 CMA, 3 ACM), Brooks & Dunn (1 CMA, 3 ACM), Luke Bryan (2 CMA, 3 ACM) and Jason Aldean (3 ACM).