You want to hear the most full-circle of full-circle moments?
Kenny Chesney has quite the connection to country newcomer, Greylan James. The two go way back — way further than any of us probably ever imagined.
Kenny Chesney’s Mom Cut Greylan James’ Hair as a Kid – Now He’s His Tour Opener [WATCH]
During a recent appearance on Katie & Company, Chesney revealed that James actually got haircuts from his mom when he was a little kid.
And we’re not talking about when James was 12 or 13. Chesney says he was about 6 years old.
“We have an East Tennessee connection. He grew up in East Tennessee. So when he was a child, my mother cut his hair,” Chesney said.
Yeah, that’s pretty darn crazy.
Kenny Chesney’s Mom Used To Cut Hair
Chesney’s mom worked in a beauty shop for years, and James’ parents would bring him in to get his hair cut.
“My mom worked cutting hair for a very long time. And Greylan’s parents would bring him in and let my mom cut his hair,” Chesney explained.
Chesney even has a picture of himself with James from when he was a kid.
He says the two were at some kind of musical event in Knoxville when James’ dad approached him and asked if he’d take a picture with his son.
“And I went, sure. And he goes, ‘He’s learning how to play guitar,’ now that person is going to be on stage with us next summer,” Chesney recalled.
That’s one heck of a full-circle moment.
Chesney called it one of those “spiritual kismet moments” and said the story is a reminder that people can be connected in ways they don’t even realize.
READ MORE: Why Kenny Chesney is One of Country Music’s Most Important Modern Artists
What Is a Spiritual Kismet Moment?
Let’s break down Chesney’s use of this mostly unused phrase. A spiritual kismet moment is a moment that feels like fate or destiny brought something together.
Basically, there’s no way this could have been planned, but somehow it all came together.
“Look, we’re all connected in ways we have no idea how,” Chesney said. “But I believe that. I believe we’re all connected.”
It’s pretty wild to think that a little kid sitting in a beauty shop getting a haircut from Chesney’s mom would eventually grow up to be an artist opening for Chesney.
Sometimes this stuff really does come full circle.
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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