When the artist of the year award is presented at the 58th annual CMA Awards on Thursday, November 20, we could see history being made. If Lainey Wilson wins for the second year in a row, she will become just the second woman to win two years in a row. 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 entered and won entertainer of the year the first time they were nominated. Wilson accomplished the feat last year. Not since the 1970s have we seen first-time entertainer of the year nominees regularly win the award. 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 finally wins his eighth nomination in the category, he will cease to be the most nominated artist in the category without a win. (That distinction would go on to be held by Carrie Underwood, who is 0-6 in the category.)
The other two contenders in the class are Luke Combs, who is seeking his third class win in four years, and Morgan Wallen, who is running for the third year in a row. He hasn't won yet.
According to the CMA website, the CMA Artist of the Year Award “regards the act that demonstrates the greatest skill in all aspects of entertainment. The voter should consider not only recorded performance, but also personal performance, audience 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 was the first team to receive the award. 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.
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Barbara Mandrell, 2
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 entertainer of the year awards.
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Hank Williams Jr., 2
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.
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Vince Gill, 2
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.
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Taylor Swift, 2
Won: 2009, 2011
Major Awards: 9 CMA Awards, 14 Grammys.
Swift was just 19 when she won for the first time, making her the year's youngest winner in history.
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Luke Bryan, 2
Won: 2014, 2015
Major Awards: 2 CMA Awards.
Bryan is the only repeat entertainer of the year winner who has never won in any other category.
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Keith Urban, 2
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 born outside the US
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Luke Combs, 2
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 Vocalist of the Year.
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Alabama, 3
Won: 1982, 1983, 1984
Major Awards: 9 CMA Awards, 2 Grammys. Country Music Hall of Fame: 2005
Alabama was the first three-time entertainer of the year winner. They were also the first group or duo to win the award – and remain the only group or duo to win it multiple times.
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Alan Jackson, 3
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 non-consecutive awards in the category.
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George Strait, 3
Won: 1989, 1990, 2013
Major Awards: 17 CMA Awards, 1 Grammy. Country Music Hall of Fame: 2006.
Straight's winning streak spanned 24 years, a record at the time (but since eclipsed by Garth Brooks). Straight has received a record 19 nominations for artist of the year, meaning he has missed out a record 16 times.
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Kenny Chesney, 4
Won: 2004, 2006, 2007, 2008
Notable Awards: 11 CMA Awards.
Chesney is the only artist to win four times in five years.
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Garth Brooks, 7
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 Award for Popular Song: 2020; Kennedy Center Honors: 2020; Nashville Songwriters Hall of Fame: 2011
Brooks first won artist of the year in 1991, just a year after winning 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 then picked up two more wins, before graciously agreeing to stand aside and give other artists a chance. His 28-year winning streak is also a record.
from our partners at https://www.billboard.com/lists/cma-awards-entertainer-of-the-year-winners-multiple-times-complete-list/
