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Kenny Chesney: The Superstar I Never Saw Coming | Once Around The Country episode artwork

EPISODE · Sep 16, 2026 · 16 MIN

Kenny Chesney: The Superstar I Never Saw Coming | Once Around The Country

from Here's What We Know · host Gary Scott Thomas

Send us Fan Mail Our host, Gary Scott Thomas, has spent nearly 50 years in radio, and during that time he has met plenty of artists who went on to become stars. But there was one he never saw coming: Kenny Chesney. This week on Once Around the Country, Gary walks through Kenny's full journey, from a self-produced demo album sold out of the trunk of his car in Johnson City clubs to a publishing deal at the Opryland Music Group to a first record deal that ended when the label shut down to the persistence that finally landed him a deal with BNA Records. Gary also shares a personal memory from a moment in a program director's office, when a young and slightly discouraged Kenny Chesney needed a laugh and a little belief from the people around him. Years later, when Kenny had become a superstar, he returned the favor by being the first big guest on KRTY’s new streaming radio station. This is a story about Kenny Chesney, hard work, humility, timing, and what happens when someone keeps going even when the path ahead isn't obvious. In This Episode: Kenny Chesney's childhood in Luttrell, Tennessee, and his athletic beginnings Attending Gibbs High School, the same school that later produced Morgan Wallen Discovering bluegrass music at East Tennessee State Meeting Alison Krauss while both were still students Selling over a thousand self-produced albums with no promotion Moving to Nashville and playing the Bluebird Cafe and the Turf Signing his first record deal on Capricorn Records in 1994 The label closing and what came next Signing with BNA Records in 1995 and his first top ten hits The moment Gary and his radio partner Julie helped Kenny push through self-doubt Kenny agreeing to help launch the radio station's move to streaming What Kenny Chesney is really like, according to someone who has known him for decades This episode is sponsored by: Bison Junk Removal Mike Counsil Plumbing & Rooter (Use code “Gary” to get $89 off any service!) License #: 679261 Bio: Kenny Chesney is one of country music’s biggest stars, but his story started far from the stadiums. A Tennessee native and former college baseball and football player, Chesney discovered bluegrass at East Tennessee State before moving to Nashville and building his career one club, song, and fan at a time. Known for hits like “How Forever Feels,” “She Thinks My Tractor’s Sexy,” and “That’s Why I’m Here,” Chesney’s career is a story of hard work, persistence, and knowing when to change course. Instagram: https://www.instagram.com/kennychesney/ Tags: Kenny Chesney, Kenny Chesney story, Kenny Chesney career, Kenny Chesney biography, Kenny Chesney early career, Kenny Chesney Nashville, Kenny Chesney country music, Tim McGraw, Gary Scott Thomas, country music stories, country music history, country music radio, Nashville music, Here’s What We Know, Once Around the Country, Kenny Chesney superstar, Kenny Chesney rise to fame Connect with Gary: Gary's Website Follow Gary on Instagram Gary's Tiktok Gary's Facebook Watch the episodes on YouTube Advertise on the Podcast Thank you for listening. Let us know what you think about this episode. Leave us a review!

Episode metadata supplied by the publisher feed · Published Sep 16, 2026

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Send us Fan Mail Our host, Gary Scott Thomas, has spent nearly 50 years in radio, and during that time he has met plenty of artists who went on to become stars. But there was one he never saw coming: Kenny Chesney. This week on Once Around the Country, Gary walks through Kenny's full journey, from a self-produced demo album sold out of the trunk of his car in Johnson City clubs to a publishing deal at the Opryland Music Group to a first record deal that ended when the label shut down to the p...

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Kenny Chesney: The Superstar I Never Saw Coming | Once Around The Country

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