Country star Kenny Chesney shared a story about his rocky start with Taylor Swift on The Tonight Show. He had to cancel Swift's tour with him due to her being a minor, but compensated her with a significant amount of money. Swift later received a generous birthday gift from Chesney, which helped her fund her dreams. Chesney also discussed his friendship with Jimmy Buffett and his upcoming residency at the Sphere in Las Vegas, where he promises a fresh and visually stunning show.