Kenny Chesney Shares His Ultimate Playlist From His Memoir ‘Heart Life Music’ — And the Stories Only He Can Tell: Exclusive

This song opened every door for me. Written as a broke kid on a couch in a funky apartment, watching “The Wizard of Oz” and thinking about how they all got what they wanted. But the poor Tin Man, he didn’t realize how much that heart could hurt.

This was the lightning that blew my mind! On a Thanksgiving night, in a blacked out arena, Conway Twitty spoke those words, one spotlight hit him – and the place came completely unravelled. I didn’t know what it was, but I wanted to find out.

They felt about their small town, the same way we did about ours. Randy, Teddy, Jeff and Mark looked like us, dressed like us, but they were rock stars. Landing in a field for a massive concert 10 miles down the road from our house? That told every one of us, people who came from where we did could be as big as the Stones, because in a lot of ways, they were.

Songs hold your life, time stamp moments. All the songs in here – and there were so many we could’ve done instead – were touchtones for my friends David and Tim, Lance and Matt Wilson who lived next door. Everyone has those songs, and everyone should hold them close.

This song was one summer, living on a houseboat with David Farmer out at the lake. But the truth is we used to sit in the Farmers’ basement listening to Fly Like An Eagle and Greatest Hits over and over again. 

In a lot of ways, this was the big breakthrough song. It was a multiple-week No. 1. It had a pretty big deal — for the time – video. I always loved the fact it may be the only song in the world that name checks both Jimmy Buffett and Richard Petty.

There are so many great Tom Petty songs. “Don’t Come Around Here No More,” “Southern Accents,” too. But there is something about the way that guitar part creeps up on you, then wraps around… We did this at so many Keg shows, and whether we were in the South, New England or wherever, it kills equally.

This is the one that changed everything. I’d been trying to decide how to make my music more personal, more true – especially to everyone I knew who grew up like me. We pushed all those melodic Van Halen guitars into this tightly written song that was my life, and suddenly everybody else saw their life, too.

Uncle Kracker came to our Neyland Stadium show, and I was fired up. I loved the melody of the song and the way it moved. I actually played him “When the Sun Goes Down” on the bus that afternoon. When he told me, “That’s fresh,” I decided to make the song a duet.

If there is a song that captures my soul when I am truly still, truly at ease, this is the song. Every word of it is true, and I still have that blue wicker rocker. It’s seen a lot of miles, but man, the thoughts I’ve had sitting there. And it’s also a picture of my truest songwriter self.

Everything they did blew all of our minds in junior and senior high school. But this was so in your face, so hilarious in how wide open it was. “I brought my pencil, now give me something to write on…” at that age is ultimate Beavis and Butt-Head stuff.

Written at Sammy Hagar’s pool, after playing what I’m told is still the longest set in the history of Sammy’s birthday parties. Sweaty, played out and thrilled to be part of something like this, I took note that Sammy turning 57 wasn’t slowing down any! That’s part of what sparked the song: all the expectations do [x] or y, or what; but who said so? And so, I decided to just put all that on hold and enjoy the sun coming up.

Kracker rolled in 100% Detroit cool, and helped us turn what was clearly a hit into an anthem. I don’t know that we saw it coming, but I did know hanging at the studio that day, this was somebody who was going to be my friend for a long time.

I’d asked Willie to record “Lucky Ole Sun” with me, because I loved Stardust so much. I’d listen to it driving home after getting in from a string of shows. He liked it enough to ask Buddy Cannon and I to produce what became Moment of Forever.

Guy Clark wrote this — about stress relief, if you will. Willie knew just what it was talking about, and we got to sing it together. Talk about a peak moment. 

Dean Dillon, Mark Tamburino and I wrote this down in the islands when I was wore out – and realized looking out at the clouds over the ocean, as exhausted as I was, I had so much to be grateful for. Willie cut it first. But when I asked Dave Matthews, who’d had his own “Gravedigger” on that Willie album, he remembered the song and said, “Yes.” I love that Dave Matthews got to have a No. 1 country hit alongside everything else he did!

A total fantasy. I asked just because it was something I really wanted to do – for no reason other than how much I loved the way Willie sang it. He agreed, which is why Willie is Willie.

A friend had given me one of Grace’s independent CDs, and it was in a stack of stuff to listen to when I was on the boat all by myself. I put it on, and this song came rolling out of the speakers into the vastness of the night. I knew nothing about her, the Nocturnals – except her voice pulled me all the way in. I was transfixed. Who’d guess a few years later she’d become one of my favorite duet partners?

From that first line – When I feel that chill, smell that fresh cut grass – it is everything that high school football is about. Not only for the players, the coaches, the cheerleaders, students and parents, but the entire community. It’s important stuff, and I can’t stress that enough. It’s one of those songs I didn’t cut for me, but for anyone – and that’s just about everyone – who’s ever been in those stands in the fall, rooting for their school’s team.

A friend gave me their advance CD of Guy Clark’s album, and I saw this title. I immediately wanted to cut it – unheard – because it says so much. But then listening to the songcraft, the way he evokes so much of who Hemingway was? Sail away, sail away, three sheets to the wind/ Win some, lose some, this one’s for him… That is perfection.

There is something about how memories can make you crazy, drive you to places seeking something sometimes even more than the person. This was something so in the moment of that feeling, it haunted me – and Grace Potter was the perfect ghost for the job.

The Wailers have a very special code of living and how they treat people. It’s one of the things about the islands: people there have to depend on each other, they find ways to come together. This song was something they’d had started, and asked me to finish for a project that didn’t happen; when Songs for the Saints started coming together, it was the perfect tribute to everyone in the USVI who was creating a recovery and healing the community down there.

So many things had happened to me on the island, but people were starting to leave, to want to go back to the mainland to raise families. I realized things were changing, and a chapter of my life was coming to an end. I had the words, but couldn’t find the melody. Keith Gattis knew, maybe better than I did, all the emotions I was feeling and put it in the music.

Shane McAnally played this for me on the plane home from a writing trip. It was so fresh and true to everything the people in No Shoes Nation absolutely are, I said, “I’ll cut it when we land this plane.” Only another act had it on hold. I would never steal someone’s song, so I told Shane, “I’ll give them thirty days. If it takes that long to decide, they don’t know what this is.” But I did…

Moby was my first bus. A used white Silver Eagle that the bank lent me $250,000 when  I had nothing going on, and it stayed with me out on the road through all of it.  Over a million miles, it saw everything…. I remember telling Tom Douglas, “It’s a good thing Moby can’t talk,” and this song was born. And every word is absolutely true.

This one: absolute magic. It came to me in the middle of the night from Matraca Berg, who’d been drinking red wine with friends. And I knew how special it was, that it needed something special… I was looking for a voice. The person who’d given me the Grace Potter CD said, “Get Grace.” Suddenly, everything fell together: the song, the magic, one of the greatest friendships of my life.

This goes all the way back to Jimmy’s life in Key West, a free spirit in this place where it was all about writing, creativity and killing time among all kinds of characters, which is why I’d always loved it. When I was doing Songs for the Saints, it just felt like it needed to be on there. I ran into Jimmy in Malibu, started telling him about it – and even before I could ask, he told me he’d love to sing on it with me.

If there’s ever been a song that people need, this may be it. No matter what’s going on, you get a choice about how you’re going to respond to people. To me, this is the best way to do it, bring people together instead of getting caught up in what you don’t agree on. 

Like “Get Along,” this one goes right to the heart of how crazy this world is. When we play it live, people just throw everything they have into it. It’s a letting go/catharsis for everyone. It started as a conversation with Shane McAnally, venting over all of it – and it turned into this song that it feels like everyone is feeling.

When I first started spending time in the islands, Mindy Smith’s One Moment More had just come out. This song knocked me over. I would play it over and over on my boat and just let her voice float out over the water and into the night. It was everything.

This song stopped me in my tracks when I heard it. Talk about a study in the human condition, just that place and time. I had to do a lot of living to be able to sing this…

If there’s ever been a call to live in the moment, this is it. A total celebration of being completely alive, right where you are right now.