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Kenny Chesney has been releasing albums for over 25 years and just announced the Deluxe Version of his 2020 Here and Now album and there is no sign of the superstar stopping anytime soon. Next year, he’ll be on the road: he just pushed his next stadium tour to 2022.

It’s not easy to rate all of Kenny’s singles and everyone’s list would be different: lists are, of course, subjective. But having interviewed Chesney and talked music with him since his debut album was released in 1994, I am going to take a crack at it.

Here is my list of Kenny Chesney’s top 20 songs.

Kenny Chesney’s 20 Best Songs, Ranked