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

Here all the artists who have won the CMA award for entertainer of the year multiple times, including Garth Brooks, Kenny Chesney and George Strait.

Back then, it happened four years in a row with Roy Clark(1973), Charlie Rich(1974), John Denver(1975) and Mel Tillis (1976). Swift was just 19 when she won for the first time, making her the youngest entertainer of the year winner in history. Strait’s wins span 24 years, a record at the time (but since eclipsed by Garth Brooks).

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