Kenny Chesney attends the 64th Annual BMI Country awards on November 1, 2016 in Nashville, Tennessee.
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20 Classic Kenny Chesney Songs, From Beach Anthems to Love Ballads

Since his emergence in the '90s, Chesney has proved to be one of country's most prolific superstars.

With an incredible 16 studio albums, Kenny Chesney is one of the most prolific country superstars still at the top of his game. And when you pore over the track listing of any Chesney record, it's no wonder that he is one of few artists in any genre who's sold out football stadiums across multiple decades.

Chesney emerged in the '90s and suited the hat act moment. Like peer Tim McGraw, Chesney has remained relevant past age 50 by changing with the times without those changes overshadowing the elements that initially made him a star. Such a feat's rare in a genre that historically moves on from even its biggest stars before they turn 40, relegating them to living legend status instead of positioning them continued cultural relevancy.

The self-professed "island boy" who loves living in paradise also does a great job of singing great "life lesson" tunes. Let's take a look at 20 great Chesney songs.

Editor's Note: This article was originally published in 2017. It was expanded in Aug. 2023.

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