MUSIC CITY MINUTE

Kenny Chesney is a legend, yet he retains strong feelings over industry slight | Music City Minute

Jan 30, 2026, 11:43 AM

Kenny Chesney has sold millions of records, rocked millions of faces at stadiums around the world and is a member of the Country Music Hall of Fame. You would think with all that success a big star like Chesney wouldn’t get hung up on little things such as songs that didn’t make it to No. 1 status. However, the Tennessee native recently confessed there is one song he believes didn’t get a fair shake, and it’s stuck in his craw since 2003. Two major records dominated radio airplay that summer, Chesney’s, “No Shirt, No Shoes, No Problems” and “5 O’Clock Somewhere” from Alan Jackson and Jimmy Buffett, which sat in the No. 1 position for eight straight weeks. Although he considered both icons good friends, Chesney’s disappointment over his song only peaking at No. 2 is palpable. Revealing the innerworkings of the music business, he explained how both songs were released from the same label, but Jackson and Buffett’s song was so “hot” there was no room for the label to maneuver his song on the charts. That said, the “Pirate King of Country Music” puts a little extra into performances of “No Shoes, No Shirt, No Problems,” essentially, giving the song the love and attention it didn’t receive from the industry.
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