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.
Won: 1980, 1981
Major awards: 4 CMA Awards, 2 Grammys. Country Music Hall of Fame: 2009
Mandrell was the first repeat winner for entertainer of the year. She is the only woman to win back-to-back awards for entertainer of the year.
Won: 1987, 1988
Major awards: 7 CMA Awards, 1 Grammy. Country Music Hall of Fame: 2020; Nashville Songwriters Hall of Fame: 2007
Williams was the first male solo artist to repeat as entertainer of the year.
Won: 1993, 1994
Major awards: 18 CMA Awards, 22 Grammys, more than any other male country artist. Country Music Hall of Fame: 2007; Nashville Songwriters Hall of Fame: 2005
Gill was the first five-time winner for male vocalist of the year.
Won: 2009, 2011
Major awards: 9 CMA Awards, 14 Grammys.
Swift was just 19 when she won for the first time, making her the youngest entertainer of the year winner in history.
Won: 2014, 2015
Major awards: 2 CMA Awards.
Bryan is the only repeat winner for entertainer of the year who has never won in any other category.
Won: 2005, 2018
Major awards: 12 CMA Awards, 4 Grammys. Nashville Songwriters Hall of Fame: 2023
Urban, who was born in New Zealand and raised in Australia, is the only repeat winner who was born outside the U.S.
Won: 2021, 2022
Major awards: 8 CMA Awards.
In addition to being a repeat winner in this category, Combs is a two-time winner of both album of the year and male vocalist of the year.
Won: 1982, 1983, 1984
Major awards: 9 CMA Awards, 2 Grammys. Country Music Hall of Fame: 2005
Alabama was the first three-time winner for entertainer of the year. It was also the first group or duo to win the award – and remains the only group or duo to win it multiple times.
Won: 1995, 2002, 2003
Major awards: 16 CMA Awards, 2 Grammys. Country Music Hall of Fame: 2017; Songwriters Hall of Fame: 2018; Nashville Songwriters Hall of Fame: 2011
Jackson was the first male solo artist to win entertainer of the year three times. He was also the first winner to win nonconsecutive awards in the category.
Won: 1989, 1990, 2013
Major awards: 17 CMA Awards,1 Grammy. Country Music Hall of Fame: 2006.
Strait’s wins span 24 years, a record at the time (but since eclipsed by Garth Brooks). Strait has received a record 19 nominations for entertainer of the year, which means he has lost a record 16 times.
Won: 2004, 2006, 2007, 2008
Major awards: 11 CMA Awards.
Chesney is the only artist to win four times in a five-year span.
Won: 1991, 1992, 1997, 1998, 2016, 2017, 2019
Major awards: 14 CMA Awards, 2 Grammys. Songwriters Hall of Fame: 2011; Country Music Hall of Fame: 2012; Gershwin Prize for Popular Song: 2020; Kennedy Center Honors: 2020; Nashville Songwriters Hall of Fame: 2011
Brooks first won entertainer of the year in 1991, just one year after he won the horizon award (the former name of new artist of the year). In 1998, Brooks became the first four-time winner. In 2016, he became the first five-time winner. He subsequently pocketed two more wins, before graciously agreeing to stand aside and give other artists a chance. His 28-year span of wins is also a record.