KENNY CHESNEY GETS COMFORTABLE IN KEY WEST 

Kenny Chesney’s affinity for Key West is evident in the video for his new single, ‘Carry On,’ which features Key West artist David Wegman and was filmed almost entirely at Schooner Wharf Bar. KENNY CHESNEY/TikTok

Kenny Chesney gets it.

The real Key West. Not the polished perfection of a vacation paradise. The year-round, untucked, unfiltered and irregular version. 

Key West clicked with the country music superstar when he first started kicking around town more than 20 years ago. Back then, he could have some drinks at the Conch Farm without drawing too much attention.

He even owned a home on Caroline Street — until it became an unofficial tourist attraction. But that didn’t diminish his affection. 

Chesney didn’t pick Key West; it picked him. This island has a knack for finding the people meant to be here.

Chesney’s newest single, “Carry On,” and its accompanying video proves it. 

Shot mostly at Schooner Wharf Bar, which Chesney mentions by name in the lyrics, the video also features one of those other people Key West picked — David Wegman, the longtime Key West artist and local personality. The video also shows concert clips from Chesney’s sold-out stadium shows, contrasted with footage of him effortlessly riding a bike through Old Town and strumming a guitar on the deck of a boat.

Key West may not be the same place it was when Chesney first came down, but it’s still better than anywhere else. 

“Carry On” lyrics:
She was 69, still smokin’
Serving hurricanes since the Schooner’s Wharf opened
When she poured me one, I asked the secret
She said, “Don’t ever let grass grow up underneath you”

Carry on karaoke, it don’t matter if you can’t
Carry a tune in a bucket anyways
Carry on, who cares what the naysayers say
If it’s Saturday night, get carried away
Carry on, carry on
You can’t carry nothin’ with you, and it won’t be long
‘Til it’s six carrying you home
‘Til then you gotta carry on

Well, it turns out she kissed Elvis
The story she told would make Penny Lane jealous
And she said, “Hun, my shift’s ending”
Beside a peace sign at the bottom of my ticket

Carry on karaoke, it don’t matter if you can’t
Carry a tune in a bucket anyways
Carry on, who cares what the naysayers say
If it’s Saturday night, get carried away
Carry on, carry on
You can’t carry nothin’ with you, and it won’t be long
‘Til it’s six carrying you home
‘Til then you gotta carry on
Carry on, carry on
If it feels good, do it
If it doesn’t, then don’t…
Yeah man, you gotta carry on
Yeah man, you gotta carry on
Yes ma’am, I’m gonna carry on

Mandy Miles
Mandy Miles drops stuff, breaks things and falls down more than any adult should. An award-winning writer, reporter and columnist, she's been stringing words together in Key West since 1998. "Local news is crucial," she says. "It informs and connects a community. It prompts conversation. It gets people involved, holds people accountable. The Keys Weekly takes its responsibility seriously. Our owners are raising families in Key West & Marathon. Our writers live in the communities we cover - Key West, Marathon & the Upper Keys. We respect our readers. We question our leaders. We believe in the Florida Keys community. And we like to have a good time." Mandy's married to a saintly — and handy — fishing captain, and can't imagine living anywhere else.

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