
Photo by Stephen Clarke
Artist Jason Kennedy was born in Canada’s Northwest Territories, raised in a small mining town, and spent his formative years “bouncing around” the Great White North.
However, his work is refreshingly in tune with his Caribbean subject matters.
His work portrays an intimate knowledge of, and insight into, the Caribbean region, its day-to-day bustle, and its vibrant soul away from the touristy scenes that are only one layer of a multi-faceted onion.

Artistic journey
Jason swapped snow for sand in 2008 when he uprooted his life in Canada and travelled south to Cayman.
“I knew pretty quickly that I’d want to spend a lot of time here,” he says. And that he did, rediscovering a passion for painting and firmly entrenching himself in Cayman’s creative scene ever since.
His artistic talents had taken root long before, but his journey had taken a few diversions.
“I’ve been drawing for as long as I can remember,” says Jason. “Some of my earliest memories are drawing creatures on paper that I would tape together so I could make extra-large sketches. I was obsessed with monsters, like every kid in the early 80s. In high school, kids would pay me to draw their cover art for literature projects.”
Jason left high school and enrolled in a visual arts course at York University in Toronto.
“But I was a really distracted 18-year-old, so after the first year I didn’t return,” he says. “I recall it being a mutual decision.”
Years of working sales jobs followed, but Jason rediscovered a passion for painting when he moved to Cayman.
“I’ve been lucky enough to turn my hobbies into my career,” says Jason, who, as well as painting, runs The Retina Group, a media company focusing mainly on content creation for businesses in Cayman and the wider Caribbean.

Method
Jason captures his subject matters on camera, before committing them to canvas.
“All of my paintings are from photos,” he explains. “Sometimes a painting will consist of three or four photos, because one image of fish looked better than the other, while one face image was better. So, I often have a few photos in front of me that will make up one final portrait.”
When it comes to media, Jason favours oils and turpentine but admits the small confines of his studio sometimes leave him “accidentally buzzed” when using these substances.
“Acrylics work quicker, and I’ve recently started infusing drops of sea water from Seven Mile Beach into the colours,” he says. “I love the idea that a bit of Cayman lives in the painting.”
And he’s not the only one. Jason has amassed many fans, and purchasers of his art are a mix of Cayman residents and overseas buyers – bodybuilder and actor Lou Ferrigno being one of them.
“Residents in Cayman always feel a sense of pride about owning locally made artwork,” explains Jason.
“The community here has an unwavering support for artists. I’ve also shipped a lot of paintings to the US. I think people see the artwork while on vacation and, because they don’t live here, they want to take home something that will constantly remind them of the connection they made to the island.”
On-island, Jason’s works can be often be seen at The Ritz-Carlton, Grand Cayman, Pure Art and Kennedy Gallery (“Not mine, just a nice coincidence,” he says).

Driving factor
Unsurprisingly, his inspiration is drawn from the Caribbean.
“My subject matter is quite obviously Caribbean, and, specifically, people of the islands. So, in a place like this, inspiration is everywhere,” he says.
“I get inspired by people I see in Cayman or in travels. During my last trip to Jamaica, I was blown away by the lagoons and hills in Port Antonio and the fisherman there. So, at the moment, I’m pretty hungry to put some paint on a canvas.”
But don’t expect to see Kennedy commissions adorning walls of every condo or private home, he prefers to work to the beat of his own drum, and whenever inspiration strikes.
“Painting happens when I feel inspired, which is great because there are never any deadlines or pressure to execute,” he says. “It’s done on my own watch, without
any direction.
“I’ve been fortunate enough to have people appreciate the work that I create. I’ve found that when I’m inspired, I want to paint. And when I want to paint, I do my best work, because I’m excited about finishing a piece that moved me.”

Originally published in InsideOut magazine, Issue 37, Spring Summer 2020.
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