Chesney chatted with co-author Holly Gleason for 90 minutes
Kenny Chesney’s new book Heart Life Music takes fans on a timeline of his life, beginning with church, family, school, and sports. He grew up wanting to play baseball for the Boston Red Sox until he saw Conway Twitty take the stage near his hometown in East Tennessee one Thanksgiving when he was eight. Shortly thereafter, his inspiration grew when he witnessed a performance by Alabama. He quickly abandoned his dream of becoming an athlete for a career as a performer, and never looked back.
The country superstar, who was recently inducted into the Country Music Hall of Fame, brought some of the stories to the Saban Theatre in Beverly Hills on Friday night (Nov 7th) for the final stop of his sold-out book tour. He and co-author and award-winning journalist, Holly Gleason, chatted for 90 minutes as the audience willingly put their phones away and lived in the moment. The book talk was a freewheeling trip through the soul-searching process of how Chesney has become one of the biggest superstars in country music.
He discussed his time as a member of the East Tennessee State University (ETSU) Bluegrass Program in Johnson City. He was also part of the renowned Bluegrass, Old-Time and Country Music Studies Program, the only one of its type in the country. Chesney has credited the program and its founder, Jack Tottle, with inspiring his musical career and teaching him the discipline of writing and performing.
Chesney also recounted being rejected by a female classmate while in college. He had a crush on a girl who sat beside him in a Persuasion class. He spent about six months trying to convince her to go out with him when he decided to write a song for her—the first song he ever wrote. He recorded it on a cassette tape and slid it to her, but when he returned to class the following week, she sat “as far back in the corner of the room as she could sit,” signaling that she wasn’t interested. It marked the “first taste of rejection in the music business, and as a songwriter,” which inspired him to move to Nashville after graduation in 1991.
As most aspiring musicians do, Chesney took on various jobs while pursuing his career. In 1992, he received his first songwriter’s contract with Acuff-Rose, a legendary and highly respected music publishing company co-founded by Roy Acuff and Fred Rose, who published many of Hank Williams’s iconic songs. Chesney credits spending time in his lowly Nashville apartment for writing “The Tin Man,” inspired by a viewing of The Wizard of Oz, which helped him land the publishing deal that paid him $150 per week. A year later, he signed his first recording contract with Capricorn Records and released In My Wildest Dreams in 1994. The label shuttered its Nashville country division, and Chesney signed with Sony Music Nashville’s BNA Records, where he released All I Need To Know in 1995, launching his ascent to superstardom.
A poignant moment of the evening came when Chesney discussed releasing an 18-song Greatest Hits record in 2000, which led him to rethink his career. Despite having hits throughout the 90s, he says no one knew who he was. During a two-year hiatus, he focused on writing what would become some of his signature songs, like “No Shoes, No Shirt, No Problems,” “I Go Back,” and “Young,” to name a few.
However, it was nearly a decade later that he decided to step away. In 2010, he discovered the song “The Boys Of Fall,” which was written by Casey Beathard and Dave Turnball. Beathard had a personal connection to the song’s theme, as his son, C.J. Beathard (who later played quarterback in the NFL), was playing high school football when the song was written. Chesney was immediately drawn to the song because it perfectly captured his own experience growing up and playing football. He prepped footage for a music video but was inspired to expand it into a full-length documentary with ESPN.
The 90-minute film featured interviews with numerous legendary football players and coaches, including Peyton Manning, Joe Namath, Brett Favre, John Madden, Sean Payton, and others, all reflecting on their high school football experiences. The core message is how the hard work, humility, teamwork, and discipline learned on the football field shape players—especially those who don’t go on to play professionally—into the people they become.
Chesney said he thought about quitting the music industry at the time, but the song and documentary “saved my creative life.”
The discussion was filmed for a future virtual event designed to give all of No Shoes Nation a chance to experience it.
