The top touring artist in country music history bucked the system and assembled something closer to diary entries than stadium singalongs.

On this sunny day in Sony Music's Nashville offices, Kenny Chesney is handed a printout of his chart history on Billboard's Hot Country Songs tally, which boasts 45 top 10s and 1,169 chart weeks--and counting. "I've never seen this," he says, shaking his head. "Man, I had a mullet when 'Whatever It Takes' came out [in 1994]. Are you kidding me? This shows a journey. It shows a dream. It shows a lot of changes, emotionally, personally. All the people I sang with-Dave Matthews, Grace Potter, the Wailers, George Jones, Jimmy Buffett, Kid Rock, Willie Nelson, Joe Walsh.

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