Greatest Hits

This 2000 collection is the definitive snapshot of Kenny Chesney's ’90s trajectory. By tallying his biggest singles of the era, it spotlights every side of the country superstar's sound. The randy, twang-soaked "She Thinks My Tractor's Sexy" shares space with "That's Why I'm Here" (an emotional tale of an alcoholic's struggle) and the heart-on-sleeve romantic ballad "You Had Me from Hello." And the addition of a few newly recorded cuts—including the achingly vulnerable album opener—makes this essential even if you have all his ’90s albums.