The revelation comes on Page 180.
There are plenty of epiphanies throughout “Heart Life Music,” Kenny Chesney’s New York Times bestselling autobiography written with acclaimed author Holly Gleason, who skillfully erects the emotional framework that the country music superstar builds the story of his life upon.
But this one feels especially resonant — definitive, even — Chesney identifying the true creative north star of his salt-of-the-earth songbook, thick with callused hands and hearts alike.
“I’d learned real life — real, real life — trumps everything else,” he writes. “People want to hear their lives, especially the seemingly difficult patches, delivered with empathy, even a happy ending they can’t see.”
This is where Chesney comes in, to bring those lives to real, real life in song.
“Heart Life Music” chronicles Chesney’s journey to this realization — and plenty more — enabling him to get to the point where his words, his lyrics “fall on the page the way they want, not the way they should be.” (There’s another breakthrough on Page 272).
With Chesney resuming his Sphere residency on Friday, here are five takeaways from “Heart Life Music” that help explain how he went from rural Tennessee to Vegas headliner.
Stars in his eyes
Small towns have a way of catalyzing big dreams — all that open space has to be filled in with something — imagination and yearning often taking the place of skyscrapers and bustling city streets.
Raised in the blink-and-you’ll-miss-it rural outpost of Luttrell, Tennessee (population 1,064, as of 2023), Chesney would lie in his yard as a kid, gazing up at the night sky.
“Staring into it, I felt a peace, but also a curiosity rumbling that’s never stopped,” he writes. “That’s where this dream started or at least the idea of dreaming. Being a child who didn’t have much to draw on — growing up in a rural town … I was dreaming to dream.”
In those days, the dream wasn’t to make music — that’d come later.
But the emotional, creative, intellectual and eventually physical wanderlust that would power Chesney’s music in the years to come can all be traced back to a young boy’s stargazing.
“I only knew the roads I was used to going down, to school, to church,” Chesney remembers. “But the stars made me wonder. I sensed those roads went places I’d like to see.
“It’s not that you want to leave,” he elaborates. “It’s that you want to know.”
Early lesson in songwriting
As an undergrad studying marketing at East Tennessee State University by day, singing at local joint Chucky Trading Company for tip money by night, one the first things Chesney always did when visiting home from college was stop by his mother’s beauty saloon, Styles Inc.
He’d sit there, reading through every issue of Cosmopolitan magazine, soaking up his surroundings the way Mom’s fingers soaked up shampoo.
“Part of being a songwriter is to listen, read, hear all the stories, watch the people and make something out of it,” Chesney explains. “Styles Inc. was real life, people and stories in a place where the filters were off and women were telling it like it was to each other.”
Years later, when Chesney would truly come into his own as an artist — because he’d learned how to infuse his songs with real life, these people and their stories.
Styles Inc. was where all that began, in earnest.
“Songs are everywhere,” Chesney notes, “if you listen for them.”
The road to stardom
After notching a slew of young-love-indebted chart-toppers early in his career — “She’s Got It All,” “Me and You,” “When I Close My Eyes” — Chesney had established himself as a successful, steadily working musician by the late ’90s.
While plenty of country music fans may have known Chesney’s songs back then, they didn’t really know him — and, really, neither did he.
“I was one more of many,” Chesney realized of his place on the Nashville hit-making assembly line.
His 1999 novelty hit “She Thinks My Tractor’s Sexy” began to change that, breaking him free from the pack a bit, though Chesney still longed for a more authentic expression of who was.
Around this time, Chesney began regularly visiting the Caribbean, simultaneously losing and finding himself among the bar workers and boaters, waitresses and West Indian natives.
“It opened my mind to many different kinds of people, ways of life and living, thinking and experiencing the world,” he says. “The more people I met, the more I realized: I need to write songs for all of them. … It was there I learned to be as you are.”
This realization directly informed Chesney’s next record, 2002’s sun-kissed blockbuster “No Shoes, No Shirt, No Problems,” a turning point in his career.
Swift realization
In 2003, Chesney was ready to hit the road in support of “No Shoes.”
The album’s fourth single “Big Star” — about a young singer chasing her dreams of becoming a star and all the obstacles in her path — quickly became a fan favorite, an anthem of aspiration and empowerment.
“Raised around women, I loved the idea of a young girl turning into a superstar,” Chesney says. “It wasn’t a boys’ club, or shouldn’t be.”
With that hit in mind, Chesney thought he’d booked the perfect opener for the tour, the embodiment of “Big Star”: a then-13-year-old Taylor Swift.
“She may’ve been young, but she was a good songwriter, had that fearless look in her eye that said, ‘World, here I come,’” Chesney recalls. “She was everything the song was about.”
But one of the tour’s beer company sponsors nixed Swift as a support act because she was under the legal drinking age.
Chesney had to drop her from the bill, but he still cut Swift a check for all the lost dates.
“She said it was the most money she’d ever seen,” Chesney remembers, “used it to pay off her bus and give her band bonuses.”
“Would she get another summer tour?” he wondered at the time. Maybe one or two …
One final revelation
“He’s a box of fireworks going off all at once.”
So Kenny Chesney says of his longtime buddy/adrenal-gland-incarnate Sammy Hagar.
A couple of decades back, Hagar invited Chesney down to his Cabo Wabo compound to play his 57th birthday party.
Chesney ended up jamming on stage for nearly four hours.
After the show, Chesney remembers sitting alone in the quiet with a guitar, working on an idea that had just come to him.
He began writing what would become “Beer in Mexico,” a song about finding yourself at a crossroads in life, not knowing which direction to take.
Then Chesney had another revelation.
“Who said I had to figure out all the answers?” he remembers thinking. “What reason was there to decide when or how I was going to grow up?”
And so he just kept playing.
“That’s how you write songs that matter,” he explains. “You live them.”
Contact Jason Bracelin at [email protected] or 702-383-0476. Follow @jasonbracelin76 on Instagram.