No Regrets and the Meaning Behind Kenny Chesney’s 2020 Ballad “Knowing You”

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Love comes and goes, and the memories of past relationships, romantic or not, have a way of creeping back into consciousness. Kenny Chesney mourns such a loss in his 2020 hit “Knowing You.”

Released on Chesney’s 19th album, Here and Now, the country ballad moves through the remembrance, gratefulness, and celebration of someone who left an indelible impact on his life and is no longer around.

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Knowin’ you, you probably got your toes in the sand
At a bar on a beach in the sun somewhere
Knowin’ you, you got something cold in your hand
Chattin’ up a stranger without a care
Knowin’ you, you’re still wild and free
And knowin’ you, you’re probably way over me


But God, we were so alive
I was a kid on a carnival ride
Holdin’ my breath ’til the moment
When you were gonna leave me too soon
But I’d do it all over
‘Cause damn, it was good knowin’ you

“This song doesn’t have to be a lover who’s gone or even a friend whose dream took them in another direction,” said Chesney of the song. “It can be someone who’s passed away, just staring into the sunset, knowing they’re living that best part of life in heaven, maybe even looking down on you and smiling.”

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Throughout the lyrics, the narrator reminisces about the smallest details about the person they still miss, along with the hope that they will one day return.

Knowin’ you was a free fall from a hundred thousand feet
When you don’t even care where you land
And knowin’ you was the kind of rush that you feel
When you finally get to sit in with the band
And knowin’ you, you’re still a tumbleweed
I only wish that you would tumble back to me

Knowin’ you, you’re still a tumbleweed
I only wish that you would tumble back to me

Written by Adam James, Brett James, and Kat Higgins, “Knowing You” captured a classic country feel that Chesney said he hadn’t heard for a long time.

[RELATED: 3 Songs You Didn’t Know Kenny Chesney Wrote for Other Artists]

“It was such a classic kind of country song you don’t hear anymore, and it was so pure,” said Chesney. “And then, the idea you’re wishing the best for the other person, kind of smiling, knowing just what they’re doing and thinking, ‘Yeah, go enjoy the moment,’ is something the best people in our lives make us feel.”

In the music video, directed by Shaun Silva and filmed in Gloucester, Massachusetts, and St. Croix, Virgin Islands, Chesney is seen grieving over someone he lost.

“As I’ve said over and over lately, the people who come into your life and then are gone, it’s for any number of reasons,” said Chesney. “But beyond missing them, you have the opportunity to recognize what they brought to your life and be thankful.”

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Chesney added, “For me, this song with that tempo, and the way the guys played it, brought back so much of the innocent hopefulness of country music, and it suggested so many people. It was one of those songs I knew we had to do.”

“Knowing You” hit No. 1 on the Mediabase country chart. It also peaked at No. 2 on the Billboard Country Airplay chart and No. 10 on the Hot Country Songs chart, while Here and Now shot to No. 1 on the 200 and Country charts.

Photo: Jason Kempin/Getty Images

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