Every Country Music Entertainer of the Year Since 1967

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2007
> Entertainer of the Year: Kenny Chesney
> Most popular song in 2007: Never Wanted Nothing More

Kenny Chesney scored his third Entertainer of the Year award in 2007, triumphing over the likes of Brad Paisley, Rascal Flatts, George Strait, and Keith Urban. That year also saw the release of his album “Just Who I Am: Poets & Pirates,” which spent 78 weeks on the Country Albums chart, peaking at No. 1.

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2008
> Entertainer of the Year: Kenny Chesney
> Most popular song in 2008: Better As a Memory

Kenny Chesney returned as CMA Entertainer of the Year for a third straight year, besting Brad Paisley, George Strait, Sugarland, and Keith Urban. “Better As a Memory” was the hit single for Chesney, and it was one of his 23 songs that have topped the country chart for his career thus far.

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2009
> Entertainer of the Year: Taylor Swift
> Most popular song in 2009: You Belong With Me

Two years after receiving the New Artist award — then titled the “Horizon Award” — Taylor Swift secured the title of Entertainer of the Year. Her No. 1 album “Fearless” won Album of the Year, “Love Story” won Music Video of the Year, and Swift also walked away with Female Vocalist of the Year.

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2010
> Entertainer of the Year: Brad Paisley
> Most popular song in 2010: Water

The often mirthful Brad Paisley was CMA’s Entertainer of the Year in 2010, winning out over Lady Antebellum, Miranda Lambert, Keith Urban, and Zac Brown Band. Paisley had two country No. 1 hits in 2010 — “Water” and Anything Like Me.” All told, Paisley has posted 18 country chart-toppers.

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2011
> Entertainer of the Year: Taylor Swift
> Most popular song in 2011: Sparks Fly

Taylor Swift won her second Entertainer of the Year award in 2011, triumphing over Jason Aldean, Brad Paisley, Blake Shelton, and Keith Urban. Swift was still combining country with pop music on her 2010 album “Speak Now,” and the album spent a notable 13 weeks at No. 1 on the Country Albums chart.