1 hits — and Kenny Chesney has 33 of them. 2.”Read More: Kenny Chesney Picks His Favorite Of His Songs: ‘It’s a Portrait of My Soul’He’s not wrong. On the Billboard Hot Country Songs chart alone, Chesney has 12 No. Chesney and Buffett were close friends until Buffett died in 2023, and the No Shoes Nation has love for both artists' island-country sound. 1 on the Country Airplay chart — but for Chesney, the Hot Country Songs chart is where the magic counts.