VIDEO: Kenny Chesney Talks New Memoir and Performs ‘You and Tequila’ Live in Stern Show Debut

Don’t let Kenny Chesney’s unofficial slogan — “no shoes, no shirt, no problems” — fool you. The easygoing, beach and boat-loving country superstar is one of the hardest-working artists in the business.

Joining the Stern Show for the very first time on Tuesday morning, Kenny told Howard all about his upbringing, musical influences, and historic career — which he chronicles in fascinating detail in his brand-new bestseller, “Heart Life Music.” He also spoke about balancing his laidback lifestyle with his deep passion for singing, songwriting, and performing for his fans. “I spend probably less money on performing than any act in history,” the recent Country Music Hall of Fame inductee told Howard with a laugh, explaining how even when he plays at a renowned venue like the Sphere in Las Vegas he doesn’t need much beyond a cowboy hat, a pair of steamed jeans, and his guitar. “I can be ready to go on stage in about four minutes to walk up and go and play.”

Making it look effortless can be hard work, however. Chesney invested considerable time and effort into learning the guitar and gaining confidence as a performer back when he was studying at East Tennessee State University. He told Howard he’d take just about any gig he could get, whether that meant performing during dinner service at a nearby Mexican restaurant or playing for tips at a bar full of drunk customers with a penchant for Jimmy Buffett covers.

As Kenny explained it, writing his own tunes proved a bit trickier. “The first song I ever wrote — I was in college and ironically enough I was taking a persuasion class … and I was trying to persuade [a girl] all semester to pay attention to me” he told Howard. “I was out of jokes, and I was out of East Tennessee charm — whatever I had — so I had nothing. So, I said, ‘I’m going to write her a song and see what happens.’”

What happened is that girl began sitting on the other side of the classroom. “Knowing what I know now about the music business and me being in it for 32 years, it was my first taste of real rejection,” Kenny admitted with a laugh.

A Pirate Jams With James Taylor and Jimmy Buffett’s Ashes

Kenny went into detail Tuesday morning about his close friendship with the late, great Mayor of Margaritaville, Jimmy Buffett. Chesney vividly recalls celebrating Buffett’s life and legacy at the 2024 Rock and Roll Hall of Fame Induction Ceremony, where he paid tribute to the “Come Monday” crooner alongside James Taylor and longtime Buffett bandmate Mac McAnally.

“It was one of those moments where I was going, ‘Wow, I never thought I’d be sitting right here,”  Kenny said before revealing that there was one other special guest in attendance that night: Jimmy himself.

“Mac comes up to me and he goes, ‘Look at this,’ and it was a small urn,” Chesney said, explaining McAnally had kept Jimmy’s ashes in his coat pocket during their performance. “So even after he passed, Jimmy found a way to join the party.”

Joe Walsh’s Advice for Dealing With Unruly Crowds

Sharing the stage with so many different rock legends has been one of the highlights of Kenny’s career, but even then things can go very wrong. The “Don’t Blink” singer told Howard he was getting ready to perform with Eagles icon Joe Walsh one time in Pittsburgh when a rowdy fan accosted him.

“I was playing the Steelers’ football stadium, and I thought it was cool to come up in the middle of the stadium [and] walk through the crowd to the stage. But the security got way ahead of me, and all of a sudden I’m by myself on the way to the stage,” Chesney recalled. “And I see this guy … and he buckles down and picks me up with his arms, right at my knees, and holds me up. And I just snapped, and I hit him right in the mouth.”

Kenny eventually made his way onstage and delivered a rousing performance, but the incident was on his mind the whole show. Backstage later, he asked Walsh what he might’ve done if someone in the crowd had grabbed him. “He goes, ‘I would’ve asked him to take me to the stage.’” Kenny recalled with a laugh.

Working With Grace Potter on ‘You and Tequila’

In addition to an epic, career-spanning interview with one of country music’s biggest stars, Stern Show listeners were also treated to live in-studio rendition of one of Chesney’s most beloved hits, “You and Tequila.”

Kenny collaborated with recording artist Grace Potter on the Grammy-nominated 2011 track. “I love Grace. She had a different audience. I had built this core-country audience, and she was like this hippie jam band girl,” Chesney told Howard before praising her talent and contributions to the track.

Listen to Kenny perform “You and Tequila” live in the Stern Show studio (below).

Kenny Chesney’s memoir “Heart Life Music” is available now. Catch more of Kenny on No Shoes Radio on SiriusXM channel 59.