Chesney explained to Billboard magazine what prompted him to cover this track: "My favorite book ever is The Old Man and the Sea. Those two characters in that book remind me of the relationship I had with my grandfather. It was an important one. I've been asked many times, on many different occasions, if there was one person you'd want to sit and have a beer with, living or dead, who would it be? And it would probably be Ernest Hemingway. He's traveled, he's met all these wonderful characters, he's written about them, he's loved, he's lost love, he's lived with regret, he's lived with depression, he's lived with so much stuff. Why wouldn't you want to have a beer and pick his brain... on a good day? And he loved life.
When I saw the title on a Guy Clark record, I was curious. I wonder what that means, wonder what he's talking about? And I listened to it, and it's a celebration of how he kind of walked between the raindrops. I do that a lot. I've spent a lot of time on my boat down in the Keys and over in Bimini and the Bahamas, and those are all places where he hung out. I haven't been to Cuba yet. But when I heard this song, it just took me to those places. It took me to a state of mind. I love that part of the song where it says, "Sail away, sail away, three sheets to the wind/live hard, die hard, this one's for him." Because I do, I live a pretty fast life. Even though I'm very healthy and regimented in my diet and everything, we live hard. We don't live as hard as the guys on Deadliest Catch, now they live hard. But we're in a different place every day, we're a lot like modern day pirates. So I get what that line is. It's not about being drunk at all. It's about being pedal to the metal. When I heard that line, it about killed me. I felt this odd kinship to that song.
I don't know what I'd ask Hemingway if I had a beer with him. We'd have to have whiskey, I guess."