Every Country Music Entertainer of the Year Since 1967

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1992
> Entertainer of the Year: Garth Brooks
> Most popular song in 1992: What She’s Doing Now

Garth Brooks, the man in the black hat, was CMA Entertainer of the Year for the second straight year in 1992, winning the honor over Alan Jackson, Vince Gill, Reba McEntire, and Travis Tritt. “What She’s Doing Now” was No. 1 for four weeks on the Billboard’s Hot Country Songs chart. Brooks also had another chart-topper that year, “The River.” Brooks has had 19 country No. 1 hits.

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1993
> Entertainer of the Year: Vince Gill
> Most popular song in 1993: One More Last Chance

Vince Gill won Entertainer of the Year in 1993 among a field of ’90s country royalty, including Brooks & Dunn, Garth Brooks, Alan Jackson, and Reba McEntire. Gill also won Album of the Year for his “I Still Believe In You,” which peaked at No. 3 on Billboard’s Country Albums chart.

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1994
> Entertainer of the Year: Vince Gill
> Most popular song in 1994: What The Cowgirls Do

Vince Gill got back-to-back CMA Entertainer of the Year honors, topping Brooks & Dunn, Garth Brooks, Alan Jackson, and Reba McEntire in 1994. Gill’s single “What The Cowgirls Do” rose to No. 1 on Billboard’s Hot Country Songs chart. His album “I Still Believe in You” cracked the top-10 for country albums in 1992.

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1995
> Entertainer of the Year: Alan Jackson
> Most popular song in 1995: I Don’t Even Know Your Name

Alan Jackson had just released his No. 1 album “Who I Am” when he won Entertainer of the Year. The record included some of Jackson’s biggest hits, including “Summertime Blues,” “Livin’ on Love,” “Gone Country,” and “I Don’t Even Know Your Name.” The other nominees for the award in 1995 were similar to those in other years during this period: Brooks & Dunn, Garth Brooks, Vince Gill, and Reba McEntire.

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1996
> Entertainer of the Year: Brooks & Dunn
> Most popular song in 1996: My Maria

Country pair Brooks & Dunn defeated Garth Brooks, Vince Gill, Alan Jackson, and George Strait to be CMA’s Entertainer of the Year in 1996. The single “My Maria” spent 20 weeks on the Billboard Hot Country Songs chart and was No. 1 for three weeks. Brooks & Dunn had a slew of hits in the ’90s, and 20 songs were country chart-toppers.