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The Kenny Chesney You Don’t Know

… with Kenny Chesney, we all win.

Kenny Chesney performs onstage
(Photo by Christopher Polk/Getty Images for dcp)

Kenny Chesney is a vibe. He is more than a singer, songwriter, and performer. Kenny Chesney has created a lifestyle. And yet, there is so much more to know about the author of Heart. Life. Music. 

If you have ever attended one of Chesney’s stadium shows, you know the tone is set in the parking lot hours before the gates open. In Philadelphia, cars, trucks, buses, and RVs start lining up for the lots surrounding the stadium as early as 3 am. And once inside, it’s a community of love. Heart. Life. Music.

Chesney Sings What He Knows

Kenny Chesney is the Great and Powerful Wizard of Oz of country music, and I had the chance to talk to Heart. Life. Music. co-author Holly Gleason (see conversation below), who gave me a glimpse behind the curtain. She told me those in the industry who read the book agree that this book is less of a memoir and more of a guide. Heart. Life. Music. takes you through Chesney’s journey, step-by-step, on how he became the mega-star he is today.

To hear Gleason tell it, Chesney grew up in rural Tennessee and writes what he knows. 

"Scared to live, scared to die

We ain't perfect but we try"

Get Along

He spends his time in his safe space, the islands (reminiscent of Myrtle Beach vacations with his mom), surrounded by hard-working people - his kind of people. Chesney stays true to that formula, true to himself, and it’s what makes his music so relatable.   

"Sister's got a boyfriend Daddy doesn't like

Now he's sittin' out back, 3030 in his lap

In the blue bug zapper light"

American Kids

Chesney is also incredibly grateful for those who show up. You can see it in his body language on stage, never bringing attention to himself, but pushing out the love from his heart.

Kenny Chesney peforms live at Kenny Chesney's Flora-Bama-Jama, a free beachplay for 40,000 on the Florida/Alabama line, behind the historic Flora-Bama on August 16, 2014 in Orange Beach, Alabama.Rick Diamond/Getty Images for Kenny Chesney

Chesney is a Champion of Women

It’s no secret that Kenny Chesney is a lover of women, but he is also a champion of women. He writes about them, sings about them, and lifts them up through his lyrics and actions. 

So she sings tonight
To twenty-thousand plus
And the young girls scream out loud
"Man, that could be us"

Big Star

Megan Moroney and Kelsea Ballerini each toured with Chesney and remain his close friends. They both paid tribute to him at his induction into the Country Music Hall of Fame, and the love in the photos proves their mutual respect and admiration. Heart. Life. Music. 

I am a strong proponent of “you get what you give,” and Kenny Chesney is proof of that. The best part is, with Kenny Chesney, we all win.

Andie Summers has been the morning show host on XTU for the past 25 years. She is a two-time CMA Major Market Personality of the Year winner and two-time Gracie Award recipient from the Alliance for Women in Media. As a content creator for XTU, Andie enjoys sharing parenting and travel tips, and loves helping you shop online with Must Haves.