From his debut album In My Wildest Dreams in 1994 to his 2024 project Born, Kenny Chesney has put out a lot of music over the course of his career.
It would be nearly impossible to narrow his massive catalog down to just five favorites – even for him.
Kenny Chesney’s Favorite Song From His Catalog
During a visit with Bobby Bones, Chesney took on the challenge of selecting his top five songs. And even though it was like choosing a favorite child, he did it.
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“Number one, probably it would be ‘Old Blue Chair,'” he reveals. “Just because it’s a portrait of my soul. It stamped a time of my life.”
“Old Blue Chair” appeared on his 2004 album When the Sun Goes Down. Chesney was more than a decade into his career, releasing seven albums prior to that one.
The song speaks to Chesney’s life on the road, chasing his dreams of music. Most of his days are viewed through the windshield of a tour bus, but he longs for the view from that old blue chair with nothing but the sand and the waves around him.
“I’ve read a lot of books / Wrote a few songs / Looked at my life where it’s going and where it’s gone / I’ve seen the world through a bus windshield, but nothing compares / To the way I see it / To the way I see it / To the way I see it when I sit in that old blue chair,” he sings in the chorus.
The chair represents peace in the midst of a busy life.
Kenny Chesney Chooses His Top Five Kenny Chesney Songs
“Number two, as a songwriter slash artist would be ‘I Go Back,'” he continues. “Number three would probably be ‘There Goes My Life.’ Number four would probably be ‘Anything But Mine.'”
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Choosing a fifth song made him pause for a second. He threw out some options like “Young” and “Summertime” before Bones reminded him that he has mentioned “You and Tequila” as a top five contender before.
He concedes to that suggestion making “You and Tequila” his number five pick.
Chesney’s storied career has landed him in the Country Music Hall of Fame and these songs prove why he belongs there.
25 Best Kenny Chesney Songs That Prove He’s Country Music Hall of Fame Worthy
What truly separates Chesney — a 2025 Country Music Hall of Fame inductee — from other artists is his third act. Six of the 25 songs on this list of Kenny Chesney’s best were released after 2010. It’s there he took some of his biggest risks, rewarding fans with some of the greatest lyrical moments and sounds of the 21st century.
We ranked the Top 25 Kenny Chesney songs using chart data, streaming and airplay numbers and staff/reader opinion. The year listed alongside the title is the year it was released as a radio single. The No. 1 song on this list exemplifies the best of what the Tennessee native is capable of.
Gallery Credit: Billy Dukes
