For years, Kenny Chesney has been a country musician unaware of his strengths, intent on making escapist beach songs ("Sometimes life ain't all that it's cracked up to be," he sings on "Reality," a manifesto in this regard) when his best tunes are often intimate portraits of ordinary people living life on the mainland. "There Goes My Life," for instance, details a man's transformation from reluctant teen to proud dad with heartwarming detail, and "The Good Stuff" pivots on a bartender telling his patron to quit escaping and try to work things out at home.
Still, the pride of Powell, Tenn., wouldn't be as popular as he is -- over the course of his career, Chesney has won four CMA Entertainer of the Year awards, released 22 No. 1 singles and 11 No. 1 albums, and sold out seemingly every football stadium from Seattle to Miami -- if those beach songs weren't fun, too. Live, they're even better, and in concert the singer transforms into the type of athlete he celebrates in hits like "The Boys of Fall," running and jumping across stages that are larger than most venues without ever losing his breath or missing a note. Meanwhile, Chesney's fans make a day of it, actualizing the not-a-care-in-the-world spirit of his music by turning the parking lot outside the arena into an asphalt resort.
Twenty years after arriving in Nashville as another hat-wearing kid who wanted to sing like George Strait, Chesney is squarely at the center of country music, with a new generation of artists -- performers like the Zac Brown Band, who toured with Chesney and followed him in collaborating with Jimmy Buffett -- now coming to Nashville trying to sing like him. This playlist helps explain why.