On Wednesday night (11/9) in Nashville, The CMA Awards will crown a new Entertainer of the Year. The nominees are reigning CMA Entertainer Luke Combs, Miranda Lambert, Carrie Underwood, Chris Stapleton, and Morgan Wallen this year.

As we near the big night for a country music star who will be crowned with the CMA’s top honor, we take a look at years past and who holds the most Entertainer of the Year wins for the evening’s most coveted prize.

Several acts won the honor twice, including Taylor Swift (2009, 2011), Luke Bryan (2014, 2015), and Keith Urban (2005, 2018). The very first artist to win the Entertainer of the Year awards twice in a row was Barbara Mandrell in 1980 and 1981. The last artist to win the honor twice in a row was Luke Bryan in 2014 and 2015.

The 56th Annual CMA Awards will air live on ABC starting at 8 PM ET.

  • Alan Jackson (three wins) 1995, 2002, 2003

    Alan Jackson

    Alan will get the Willie Nelson Lifetime Achievement Award at this year’s 2022 CMA Awards. Jackson won his ETOTY awards in 1995, then repeated the win both in 2002 and 2003.

  • George Strait (three wins) 1989, 1990, 2013

    George Strait

    George was at the height of his fame in 1989 and won that year and the next. It wasn’t until 23 years later that Strait won the trophy again in 2013.

  • Kenny Chesney (four wins) 2004, 2006, 2007, 2008

    Kenny Chesney

    Kenny’s big sell-out stadium tours contributed to his winning the Entertainer of the Year Award a whopping four times.

  • Garth Brooks (seven wins) 91, 92, 97, 98, 2016, 2017, 2019

    Garth Brooks

    Garth has the most wins in the top category and even took himself out of the running after his win in 2019 because he felt it was time to give the award to someone else.

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