Chesney wrote this mid-tempo song in 2006 about a man who wandered, "around and around and around and around." that he met while at his home on the US Virgin Island of St. John. "Everybody knew Lindy," said Chesney. "You'd just see him, walking along, talking to himself... Never quite sure what or whether he knew what was going on, and yet, he always had a smile on his face, and sometimes you really would see him playing piano in the little church when nobody was watching. I don't know why that one day I went home, and went, 'Well, this is one of those moments and one of those people you don't want to lose...' So I started writing, and the song poured out."
Chesney wrote the song as an expression of somebody that he'd never really had a conversation with, but was always just a staple of the Virgin Islands where he spends a lot of time. He recalled to Billboard magazine: "One night I was on my way home, and I walked past this church, really close to the road and the front doors where open, and I heard somebody playing piano. I just walked up to the steps, and it was Lindy playing piano by himself. I stood there a couple of minutes and just observed that.
"We live very different lives," he continued, "but I thought if you look past somebody's dirty shirt, a lot of times you'll see a pretty good person. I don't know his story, but you could tell that there was a person up there alone with his thoughts and his music, and I thought as different as we are, we have more in common than I would have ever realized. I went home and couldn't sleep thinking about that experience, and I sat out on the deck of my house and started thinking about all the years I'd seen him around, and that is how that song was born."