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NBC Insider The Tonight Show Starring Jimmy Fallon

Kenny Chesney Looks So Handsome Without His Cowboy Hat On (PIC)

Now here's something you don't see every day!

By Chris Phelan
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Country music legend Kenny Chesney doesn't go anywhere without his trademark cowboy hat — right?

How to Watch

Watch The Tonight Show Starring Jimmy Fallon on NBC weeknights at 11:35/10:35c and next day on Peacock

There's no better way to get into the perfect holiday weekend mood than drooling over a rare photo of the star without his cowboy hat on — and we have a throwback 2015 shot to prove it. Feast your eyes on Chesney attending the opening of a clothing store in Santa Monica, California, sans hat, but still unequivocally handsome.

Looking effortlessly dressed down and casually fashionable, Chesney looks like a completely different person without his iconic cowboy hat. He's almost unrecognizable!

Talk about a handsome blast from the past. And based on how Chesney looked during his January 16 appearance on TODAY to announce his upcoming Las Vegas Sphere residency beginning in May, it's clear that he's aging like fine wine.

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Kenny Chesney smiles in a white t-shirt.

"I'm excited for our audience to come to Vegas, and I'm excited to go," he explained to Craig Melvin and Carson Daly. "I've never done a residency, but this is such a unique thing that it made me really want to do it."

It sounds like 2025 will be a big year for the "American Kids" singer!

Kenny Chesney tells a hilarious Taylor Swift story on The Tonight Show

During Chesney's January 16 appearance on The Tonight Show Starring Jimmy Fallon — sporting his trademark cowboy hat, of course —  he told a true story of how he once booked a young Taylor Swift to open for him on a summer tour when she was 17 years old. Unfortunately, it was an offer that Chesney ultimately had to rescind! (Check out the embedded video above for the full interview.)

"We booked Taylor to go out on the road with us — this was several years ago, obviously — but that summer, my tour was sponsored by a beer company and they came to us right before the tour started and said we can't have a minor on the tour," Chesney recalled. "Which made sense, but I had to call Taylor personally and tell her she couldn't go on tour with me — which now seems absurd, right?" 

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Kenny Chesney speaks with Jimmy Fallon on The Tonight Show Starring Jimmy Fallon Episode 2080.

Chesney told Jimmy Fallon that he ultimately broke the bad news to the future megastar.

"So I called her, told her she couldn't go on the road, but I said, 'Look, I feel terrible,' because she was gonna lose some money," he continued. "And I gave her a specific amount of money, it was quite a bit of money, because I wanted to make it up to her. And later that year, we were both nominated for CMA Entertainer of the Year — that's how hot she was."

It was then that Chesney realized what he had to do!

"Well, she won, so backstage, I went up to her and gave her a big hug," he revealed. "I said, 'Congratulations, but give me my money back.'"

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