Kenny Chesney wants to be anything but complacent in his career.
On the March 24 episode of “Sunday Sitdown with Willie Geist,” Chesney spoke to Geist at New Jersey's MetLife Stadium ahead of his Sun Goes Down 2024 Tour.
While there, the pair spoke about Chesney's music career and how he's come a long way since his early days of singing for enchiladas in a college bar.
According to Variety, Chesney has sold more than 30 million albums to date and is hailed as one of the "top-selling country performers," grossing more than $1 billion from touring alone since 1995.
The "No Shoes, No Shirt, No Problems," singer explained he got into music while he was studying marketing at East Tennessee State University. During that time, his mom gifted him a guitar for Christmas.
"I was the kid in college sitting in a corner with a tip jar. I played at at a Mexican restaurant in Johnson City, Tennessee, called Chucky’s Trading Post, and I played for 15 bucks a night plus whatever I made in tips, which some nights was pretty good on the weekends," he said.
"Free enchiladas," he quipped.
After graduating, Chesney decided to move to Nashville and eventually signed his first record deal in 1993. The songs from his first five albums had gained so much traction that he released a greatest hits album in 2000.
But even after 30 years of success in the music industry, Chesney said it still feels like he's strumming for enchiladas in college even after numerous tours and albums, including his most recent release, "Born."
“I swear, man, in ways I still feel like I’m doin’ the same thing, I just got a lot more stuff around me,” he said. “You know, the interaction is still the same, but it’s just with a lot more people.”
In an effort to avoid becoming too comfortable with his status, Chesney says he constantly reminds himself of how far he's come.
"I’m terrified of being complacent, you know, and failure," he told Geist. "We always get into a stadium market on a Friday, and on a Friday after sound check, I’ll go to the very top and sit just by myself."
"I want to be grateful for what’s happened," he explained. "And just reflect on all the years that it took to get to this spot. But also it’s a way for me to emotionally and mentally measure how far it is to down here ‘cause I know what it looks like from the stage to up there, but if I’m goin’ to get close to connecting with these people I got to have their perspective."
Chesney said it's that perspective that keeps him humble.
"So if you wanna find me on a Friday night, I’m probably sittin’ up here alone thinking about what I’ve got to do the next night and just takin’ a moment to reflect and remember how grateful I am to be there," he added.