Home > Island Flava - Artist Jason Kennedy

Island Flava - Artist Jason Kennedy

For many artists, it's the beauty of their surroundings that moves them to put paint to canvas. For Jason Kennedy it's the people and culture of Cayman that are his inspiration and his muse.


Sitting Out, 2016

A fresh talent on the Caymanian art scene, Jason Kennedy, a long-term resident of the Cayman Islands, has been creating a stir with his stylised portraits of Caymanian characters.

Although he paints likenesses of individuals, his portraits are much more than mere faces: they are raw, honest snapshots of everyday life, depicted in bold brushstrokes and vibrant colours. His paintings offer glimpses of daily life as is lived, far from the island’s luxury resorts and modern office buildings. He finds inspiration in an afternoon game of dominos, a fish market vendor gutting a pile of snapper, or a man riding a much-used bicycle.


Fisherman Seated, 2015

Defining his personal style and finding his muse did not happen overnight, however. Although Kennedy spent a year studying fine art at York University, Toronto, in 1999, he switched the focus to business when, he says, he realised he didn’t know what inspired him as an artist.

It was not until he moved to Cayman in 2008 that he began to paint again. At first, he says, it was simply as a way to cover his walls with his own kind of art, rather than the "pastel colours and starfish clocks" typical of so many island condos.


3 Stars, 2016

“I wasn’t taking it too seriously. I didn’t know what I was doing with my style and I wouldn’t show those paintings to anyone now,” he laughs. It was his girlfriend and business partner, Monica Walton, who steered him away from his early cartoonish depictions, and helped him develop his current style, one that he describes  as “a mix of photorealism and impressionism.”

“It was really Monica’s idea to capture the more real side of Cayman – the human figures, the people who make the place unique,” he says. “Her cousin took us into some of the less developed areas, and we spent time with these guys playing dominoes and hanging out. That experience was the inspiration for the first painting in this style, which then spun into what I am doing now.”


Waiting by the Sea, 2014

Although he has exhibited and sold his work through local galleries and accepted various commissions – most notably the huge mural on the outside wall of the Cayman Cabana – Kennedy does not court commercial work or aspire to a full-time painting career.

He is fortunate to derive as much enjoyment from his day job – he co-founded Vagabaond Media, which creates promotional videos about the Cayman Islands – as he does from painting and with time, he has learned, he prefers not to compromise his own creative instincts by taking on commissions.

If he can simply paint what he wants to paint, and somebody else likes his work enough to spend their hard earned money on it, he says, that is all the validation he needs.

Kennedy may choose to approach his art as little more than a hobby, but he is nonetheless making a valuable contribution to the artistic legacy of the islands, and chronicling a simple, in many ways enviable, way of life that future generations may find only in paintings and photographs.

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