Kenny Chesney Is Still “Pissed” That This Song Never Hit No. 1

January 30, 2026 12:45 pm

Since releasing his 1994 debut album In My Wildest Dreams, Kenny Chesney has gained a following thanks to his mix of sincere love songs (“You Had Me From Hello”) and easy-breezy feel-good beach fare (“When the Sun Goes Down”).

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Releasing 20 albums across three decades, country music’s eight-time Entertainer of the Year has sent a whopping 33 songs to the top of the charts. However, during a recent appearance on Netflix’s Bobby Bones Presents: The BobbyCast, Chesney, 57, was more focused on the ones that got away.

“I’ve had more No. 2 records than probably any act in the world,” said the 12-time Country Music Association Award winner, adding that “probably 14 or 15 songs” have fallen just shy of the top spot.

This Kenny Chesney Hit Was Derailed by a Couple of Legends

As proof, he pointed to his 2003 hit “No Shoes, No Shirt, No Problems.” Off his sixth studio album of the same name, the song is everything that makes Kenny Chesney great. And yet, it spent eight straight weeks at No. 2 on the Hot Country Songs chart—unable to overcome the hurdle that was Alan Jackson and Jimmy Buffett’s “It’s Five O’Clock Somewhere.”

“Same label. Pissed me off,” Chesney said. “But that record was so hot they couldn’t maneuver it, you know what I mean?”

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It is quite unfortunate timing for two infectious songs about foregoing your daily responsibilities in favor of drinking at a tropical location to hit the charts simultaneously. While Chesney has the full force of No Shoes Nation behind him, Jimmy Buffett quite literally invented the “gulf and western” sound.

Country singer Kane Brown hopped onto social media to express solidarity. “Wowwwwwww fun fact ida been pissed to [sic],” wrote the “I Can Feel it” crooner. “Couldn’t tell it wasn’t a number 1 tho still massive hit.”

Country Star Adds More Shows To Historic Vegas Residency

Last year, Kenny Chesney made history as the first country artist (and solo act) to headline the iconic Sphere in Las Vegas. He will return to the stage for a second round this June. And due to popular demand, the “I Go Back” crooner recently announced six additional dates for July.

“This show has kept us inspired. Five nights turned into something bigger, and it only felt right to keep going,” Chesney wrote on social media. “If we’re going to do it, let’s make it count, so we’re adding SIX additional dates.”