Kenny Chesney Reveals His Favorite Song From His Own Catalogue—And It’s Not What You’d Think

Kenny Chesney’s favorite song from his own catalogue is a deep cut. During an interview on Bobby Bones’ podcast, The BobbyCast, Chesney ranked his top five favorite songs that he’s put out,

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Taking the top spot was “Old Blue Chair.” The song appeared on Chesney’s 2004 album, When the Sun Goes Does, and was never released as a single.

“It’s a portrait of my soul,” Chesney said of the track. “It stamped a time of my life.”

Chesney’s 2004 song “I Go Back” came in at No. 2 on his ranking, and was followed by 2003’s “There Goes My Life” and 2004’s “Anything But Mine” and No. 3 and No. 4, respectively.

Choosing a fifth track proved a challenge for Chesney. Eventually, however, he landed on “You and Tequila,” which he put out in 2010.

Chesney couldn’t help but throw some honorable mentions in there, stating, “But if I could do another five it’d be ‘Young,’ it would be ‘Summertime,’ it would be ‘Save It for a Rainy Day.’”

Kenny Chesney’s Year Ahead

Chesney’s interview came ahead of his return to the Sphere in Las Vegas. He was the first solo artist to headline the groundbreaking Las Vegas venue in 2025. Now, Chesney is set to return for 11 dates this summer.

“I wanted to get back in there and really push what was possible,” Chesney said of why he wanted to come back to the high-tech venue. “We all had ideas. We were told certain things. But what I really took away is how much fun—and different kinds of experiences people can have—no matter where they experience the show from.” 

With that learned experience in his back pocket, Chesney said he’s “working on new songs, some things we can’t do in stadiums, new visuals, new momentum to the set” for his summer concerts.

“Having watched No Shoes Nation taking it all in, we have a much better sense of how to make Sphere even more,” Chesney said. “Sphere pulled me into so many songs the fans know and love in new ways. And it deepened how I see them. The production possibilities consume you, so we had to go back to really get everything out of it.”

Photo by Erika Goldring/Getty Images for BMI