Every Country Music Entertainer of the Year Since 1967

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1997
> Entertainer of the Year: Garth Brooks
> Most popular song in 1997: Longneck Bottle

Five years after his 1992 win, Garth Brooks was honored as Entertainer of the Year for the third time. Brooks also released that year his album “Sevens,” which featured two No. 1 country hits with “Longneck Bottle” and “Two Piña Coladas.”

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1998
> Entertainer of the Year: Garth Brooks
> Most popular song in 1998: To Make You Feel My Love

Hit machine Garth Brooks made it two consecutive CMA Entertainer of the Year victories in 1998. The single “To Make You Feel My Love” went to No. 1, one of the artist’s 19 singles to top the country charts. Brooks also had two albums reach No. 1 on the country chart in 1998.

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1999
> Entertainer of the Year: Shania Twain
> Most popular song in 1999: Man! I Feel Like A Woman!

Shania Twain was still releasing singles from her massively successful 1997 album “Come On Over” in 1999. In total, 12 of the album’s 16 tracks were released as singles. By the end of 1999, the record would be certified 16x Platinum, eventually being certified double-diamond. Other Entertainer of the Year nominees were Garth Brooks, Dixie Chicks, Tim McGraw, and George Strait.

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2000
> Entertainer of the Year: Dixie Chicks
> Most popular song in 2000: Cowboy Take Me Away

Before they courted controversy with remarks about President George W. Bush and the Iraq War, the Dixie Chicks won the CMA Entertainer of the Year award in 2000, topping Faith Hill, Alan Jackson, Tim McGraw, and George Strait. The group’s single “Cowboy Take Me Away” was No. 1 for three weeks.

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2001
> Entertainer of the Year: Tim McGraw
> Most popular song in 2001: Angry All The Time

Tim McGraw won his sole Entertainer of the Year award to date in 2001. That same year, he released his album “Set This Circus Down,” which would spend six weeks at the No. 1 position on Billboard’s Country Albums chart. The album included the chart topping hits “Grown Men Don’t Cry,” “Angry All the Time,” “The Cowboy in Me,” and “Unbroken.”