Thompson Square have been making country music for more than two decades, and in that time, they’ve developed a love/hate relationship with Country Music Hall of Famer Kenny Chesney.
The “Are You Gonna Kiss Me or Not” duo were guests on Taste of Country Nights, and we asked for a few words on Chesney, who’s being formally inducted into the CMHOF later this year.
Boy, did they deliver.
“I kinda don’t like Kenny Chesney, and I’ll tell ya why,” Keifer Thompson began.
“When I moved to town in 1996, I found this song called ‘When I Close My Eyes.’ It hadn’t been cut yet. We were gonna get this [record] deal, this song was gonna be the first single,” he recalls.
He remembers arriving to Nashville in a 1989 Chevy Blazer with a U-Haul attached to the back, ready to record “When I Close My Eyes.” They were excited.
He needed a regular job first, to have some change in his pocket.
“I go to a Western store called Nashville Cowboy, took the wanted sign out [of the window] and said, ‘I ain’t leaving ’till I got a job.’ She said, ‘Alright, you’re hired.'”
Things were going well, until …
“A couple of days later, I’m vacuuming the floor, it’s closing time, and I hear, (singing) ‘When I close my eyes,’ and I’m just like, ‘You’ve gotta be freaking kidding me!'”
At this point in time, Chesney had released eight singles, and three had cracked the Top 10 on the Billboard Hot Country Songs chart. He was quickly becoming a reliable hitmaker.
Thompson couldn’t help it — once he realized it was Chesney’s voice on the song he’d been dreaming of cutting, he decided Kenny Chesney wasn’t his favorite person. It’s a friendly love/hate vibe that exists to this day, nearly 30 years later.
“When I Close My Eyes” was Chesney’s ninth single, and it made it all the way to No. 2.
Keifer Thompson’s opinion on the soon-to-be Hall of Famer is all in good fun, of course. He admires Chesney for the path he’s carved for others.
“He’s just been a constant through the decades, not changing anything,” he observes, noting how Chesney has stayed true to who he is and keeps his brand in line.
His wife and duo partner Shawna Thompson chimed in, as well, saying: “Talk about picking great songs and knowing who you are as an artist, doesn’t get any better than that.”
See? It’s all love.
Chesney, June Carter Cash and producer Tony Brown are the newest inductees into the Country Music Hall of Fame, class of 2025. They’ll be formally enshrined in a Medallion Ceremony in October.
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
PICTURES: See Inside Kenny Chesney’s Spectacular $11.5 Million Tennessee Estate
Kenny Chesney has sold his 4-bedroom, 9-bathroom, 12,599-square-foot hilltop estate in Tennessee for $11.5 million, and pictures show an opulent Mediterranean villa that is lavish even by the standards of other celebrity mansions.
Gallery Credit: Sterling Whitaker
