Kenny Chesney is used to selling out stadiums and performing to huge crowds, but that doesn’t mean he’s always comfortable in the spotlight.
During a new appearance on Rob Lowe’s Literally! With Rob Lowe podcast, Chesney admits that certain social situations kind of freak him out — especially when he has to address a crowd of people with his speaking, not singing, voice.
“Have you ever been in a situation where you’re in a group of, like, 20 or 25 [people] before a meal and someone randomly asks you to say the prayer?” Chesney asked Lowe during that conversation.
Read More: Kenny Chesney is Pulling Out Deep Tracks For His 2026 The Sphere Residency
“That’s so much anxiety,” the singer continues. “I crumble.”
Why Does Kenny Chesney Get Nervous Before Speaking Engagements?
The subject came up while the two stars were discussing Chesney’s recently-released memoir, Heart Life Music, and the fact that he followed the project’s release with a book tour.
“It was really hard for me at first,” Chesney said.
“I’m used to singing to 60,000 people, but you ask me to speak to 600, it’s a completely different thing,” he continued. “But I’m getting better at it.”
Chesney also recorded the audiobook of Heart Life Music himself, though he says he still finds the sound of his speaking voice a little strange to hear back.
Jason Kempin, Getty Images
Smaller speaking engagements aren’t the only unfamiliar territory Chesney’s been tackling recently. He also said that it was an adjustment for him to figure out how to perform at the one-of-a-kind venue The Sphere during his Las Vegas residency.
Kenny Chesney Forgot the Words to His Songs During His First Night at The Sphere
The Sphere is renowned for unique production capabilities. Though Chesney’s used to lights and other special effects flashing on stage behind him, he admits it took some time to adjust to just how immersive production is at The Sphere.
In fact, the first night of the residency, he forgot the words to some of his own songs.
“I was completely lost in the middle of my own song,” Chesney told Lowe with a laugh. “…I admitted it to the audience, and I’m like, ‘Help me, I’m lost because I’m looking at all this stuff.’ It was kind of a bonding moment in a way.”
Chesney will return to The Sphere for a new run of shows in 2026.
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