Kenny Chesney became a reigning 21st-century country star by making himself the voice of sheer contentment. In his honey-dipped baritone, Mr. Chesney just about always sang about the pleasures of a stable, settled life and about how everything works out for the best, from beachfront getaways (“No Shoes, No Shirt, No Problems”) to an unexpected pregnancy (“There Goes My Life”). His music stayed on the cozy side of arena country, putting a little bit of modern Nashville into his mixture of 1970s soft rock with Jimmy Buffett’s Caribbean lilt.