Fellow singer songwriter and friend Jimmy Buffet with Kenny Chesney. (Photo courtesy of Kenny Chesney)
When Kenny Chesney headlines the Miami Book Fair, he isn’t just bringing his music — he’s bringing stories that span a lifetime. He’ll be joined at the Evenings With by friend and longtime collaborator Holly Gleason, who co-authored the book and has worked closely with Chesney through the years,
Country singer Kenny Chesney speaks of Key West, one of his most creative places for songwriting in his new book “Heart Life Music.” He'll be at the Miami Book Fair as one of the headliners at the opening on Sunday, Nov. 16. (Photo courtesy of Kenny Chesney, Harper Collins)
The Miami Book Fair opens on Sunday, Nov. 16 and runs through Sunday, Nov 23.
She explained how they wrote the book.
“We went to all the places in Kenny’s life that are really important, and we would be there four to six days … do two, three to four hour sessions every day.”
Key West emerged as a creative haven. “We wrote probably a third of this book in Key West,” Chesney said. “I wanted to write this book in all the places that inspired me along the way. It was fun, it was authentic, and I’m glad we did that.” The island’s creative spirit captivated him: “I was always drawn to the creative side of it. I loved Hemingway. I loved the lore of that … I’ve always felt very creative when I was there.”
The book is about more than music. It’s about the moments — and the friends — that shaped Chesney’s life. “Holly’s been with me almost every step of my journey, and there was no one, I mean, no one more qualified to write it,” Chesney said. “Nobody could have written this book, other than Holly.”
So, what can Miami Book Fair attendees expect from Chesney and Gleason’s session? “If you want to sit and have a beer with Kenny Chesney … that’s what this is going to be. This is going to be new friends and old friends on a bar stool,” Gleason promised. “There’s nothing about it that’s not authentic,” added Chesney. “We’ll give everybody in the audience more of us.”
Kenny Chesney and Holly Gleason in Key West where they spent time writing Chesney's book, which features the country singer-songwriter's musings about spending time in the Conch Republic. (Photo courtesy of Kenny Chesney)
For Chesney, authenticity is everything — both on stage and off. “Music and sports bring people together like no other thing … but I think now more than ever, people are craving authenticity,” he said. “There’s not a disingenuous chapter or a paragraph in this book.”
Alongside her collaboration with Chesney, Gleason has Miami roots—she attened University of Miami and worked at the Miami Herald while in college.
Gleason shared that her journey took her from Cleveland, Ohio, to South Florida, where she played golf for St. Andrew’s and eventually attended UM.
It wasn’t long before she was leaving her mark on local music journalism: “I started trying to write for the Miami Herald probably August or September of my sophomore year. And I think it took to about October… the entertainment editor… couldn’t find anyone to write country… Somebody said, ‘that kid knows country music,’ and he’s like, ‘You’re kidding me, right?’” Gleason’s tenacity led her to cover everything from country acts to iconic artists like Dolly Parton and Neil Young, and a longstanding friendship with Chesney that has her returning to Miami with the book she helped to co-write.
Gleason was the inspiration for the book’s title, said Chesney.
“At the end of every one of Holly’s emails for the last 20-something years, her email would say “heart, life, music” and we had conversations about what that meant – that you take what's in your heart and you live, you live your life authentically by what's in your heart. And luckily for me, I had music to connect all those dots, because music was in my heart.”
Kenny Chesney says his book "Heart Life Music" isn't a memoir but a coming together of everything he's done up until now. (Photo by Danny Clinch)
- WHAT: “An Evening With Kenny Chesney and Holly Gleason
- WHEN: 7:30 p.m., Sunday, Nov. 16, at MDC Wolfson Campus, Chapman Conference Center-3210; 300 N.E. Second Ave., Bldg. 3, Miami.
- HOW MUCH: $35, $22.66 for “Friends of the Fair.” Prices include a copy of the book.
- INFORMATION: miamibookfair.com