Kenny Chesney Looks Back on Some of His First Gigs Playing for Tips and Free Enchiladas in Johnson City, Tennessee

Today, Kenny Chesney is one of the biggest names in country music. He has sold millions of albums and packs stadiums across the nation. More than that, his fans love the music he releases. He dropped his latest album on Friday (March 22) and, less than a week later, some of the album’s tracks already boast over a million streams. That wasn’t always the case, though. Chesney had humble beginnings in East Tennessee.

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Recently, Chesney appeared on Sunday Sitdown with Willy Geist. During the conversation, he told the Today Show correspondent about some of his first gigs and how little things have actually changed for him over the years.

[Kenny Chesney Sun Goes Down Tour 2024: Get Tickets]

Kenny Chesney Performed for Free Enchiladas

Chesney came to Nashville in the early ‘90s and worked as a songwriter until he landed a record deal. After that, he notched several No. 1 hits and released a greatest hits album. However, he didn’t reach his current level of fame until he came into his own with No Shoes, No Shirt, No Problem. Before all of that, he was just a small-town college kid who played where he could for free food and tips.

Chesney found his love of music while studying marketing at East Tennessee State University. His mother bought him a guitar for Christmas, and he started playing it, and never looked back. “I was the kid in college sitting in the corner with a tip jar,” he recalled.

[RELATED: Kenny Chesney Reveals How He Uses Mindfulness and Gratitude to Avoid Complacency]

“I played at a Mexican restaurant in Johnson City, Tennessee called Chucky’s Trading Post,” he recalled. “I played for 15 bucks a night plus whatever I made in tips. Some nights it was pretty good, on the weekends. Free enchiladas. That’s pretty good when you’re in college,” he added.

He has come a long way since those early days. However, he says things haven’t changed that much. “In many ways, I still feel like I’m doing the same thing. I’ve just got a lot more stuff around me. The interaction is still the same, it’s just with a lot more people,” he explained.

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