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Holiday records tend to reveal an artist at their most unguarded.
When Kenny Chesney released All I Want For Christmas Is a Real Good Tan in 2003, the album balanced beachside escapism with something far more intimate - a reverence for family and a change in tradition that would quietly culminate in his rendition of 'Silent Night'.
Having spent much of his time when not on tour on his beloved havens of St. John and St. Barts in the beautiful US Virgin Islands, Chesney was never going to craft a traditional-sounding Christmas album, whether that be of a choral nature or classic big band jazz service.
In true Kenny style, All I Want For Christmas is A Real Good Tan is rooted in the steel-pan percussion, bright brass and lackadaisical guitar of the islands, giving a standard like 'Jingle Bells' a truly unique take, complete with a fresh verse from the man himself; "There's nothing like St. Croix / With the palm trees swaying slow / Or being there on an open dock / When the New Year comes and goes".
Beyond the desire for a sunny escape from the cold that permeates the album, there’s a quieter story. On his rendition of the Christmas traditional, ‘Silent Night’, Chesney invited his mother and aunt into the studio, creating a family moment that still resonates nearly two decades later.
In his book, HEART*LIFE*MUSIC, Chesney candidly reflects on the time around the release of the Christmas album, when his career was truly taking off following the release of his massive album, No Shoes, No Shirt, No Problems, and after ten years of working at his craft.
"There was a moment in 2003 or 2004 when I'd come home for the holidays. Every year, it's the same. Cedar Ford Baptist church, then my grandmother's house to eat her peanut butter fudge, all those vegetables she'd slow-cooked, the biscuits, ham. My Aunt Missy, by then, had learned how to do the chicken and dumplings".
"Everything felt like always, and we were us. We'd laugh at all the same jokes, tease each other. Nothing hurtful, just enough to show you were loved," Chesney continues.
"Mom, though, looked at me with concern. She was happy for me, proud. But No Shoes [No Shirt, No Problems] went from chasing-a-dream busy to warp speed. Finally, she pulled me aside and said, 'I feel like I can't reach you anymore'”.
"I knew what she meant. I was gone, mentally as much as physically. I gave her a hug, acknowledging what she said, but I couldn't change it. Nothing was going to slow down; I knew that".
The admission from Kenny is one of many moments in the book of poignant admission and an example of his drive and desire to succeed. Once you've heard the story, it makes the Christmas recording of 'Silent Night' with his family sound and feel all the more special.
While unmistakable in its melody, Kenny's version of 'Silent Night', with its playful classical guitar and Kenny's calm trill echoing across the track like a snowflake in the wind, is perhaps both the most moving moment on the album and what could be deemed the most traditional.
When Kenny's mother and Aunt join him in harmony for the outro, it's clear talent runs in the family - all three voices joined in gracious and peaceful melody for a beautifully stirring rendition.
Kenny's Mother, Karen, and his Aunt - her twin sister - Sharon, would be credited as the Grigsby Twins on the album liner notes, a nod to both their maiden names and the stage name that they carried across venues in East Tennessee.
In a wonderfully unique and nostalgic newsletter dedicated to the society of Grigsby's and the lore around the family name, entitled The National Grigsby Family Society Grigsby Gazette, published in 2003, there is a fascinating piece centred around Kenny and his Grigsby heritage, sharing how they would celebrate the Christmas holidays that year.
"Like many Sundays, Chesney’s mother, Karen, and her twin sister, Sharon, join the numerous aunts, uncles and cousins who share funny stories in the living room as they eat pot roast, potatoes, green beans, corn, deviled eggs, red velvet cake and banana pudding," the newsletter reads.
“I’m on a diet basically all year, but when it’s Christmas time, I come up here and eat chocolate pie and peanut butter candy,” Chesney says, in conversation with Beverly Keel for American Profile, which is featured in the mailer.
“The Grigsby Twins is what they were known as back when they were kids, singing around East Tennessee. My grandfather would haul them all over to sing for folks, wherever he could put them up. And now it’s my turn to drag them all over and make them sing.”
While we're sure success was never a consideration for Chesney when nestling in the studio with his family for the festive recording, it sure paid off nonetheless. The album was a major success, certifying as platinum in sales in the United States and enjoying entries across Billboard's all-genre and country charts.
The album's October 2023 release was so highly anticipated that queues at Minneapolis' Mall of America, beginning three days before the release, were long enough to prompt the installation of heating units and porta-potties for those waiting.
"I don't know that anything I'll ever do around the holidays will have that kind of response", Kenny reflected 11 years later, upon the release of his song, 'Christmas In Blue Chair Bay'.
"But I do know that my family really loves Christmas - and I was in the mood, especially with the time I've been spending in Barbados with my rum, to try and distill how slow and sweet the holidays in the islands are when we can get there."
Ultimately, All I Want for Christmas Is a Real Good Tan was more than just a holiday album - it’s a window into Kenny Chesney’s world: sun-soaked escapes, family traditions, and the quiet moments that shape a life.
By blending island rhythms with heartfelt storytelling and inviting his family into the studio, Chesney crafted a record that is both unmistakably his own and universally resonant.
It’s a celebration of warmth, togetherness, and the small, fleeting moments that make the holidays memorable - a reminder that, for all his fame and success, Chesney’s greatest music often comes from the heart, and from home.
For more on Kenny Chesney, see below:
