Budding artist chases portrait dream

January 29, 2026
One of Daniel Cunningham’s portraits captures the quiet intensity of a young woman.
One of Daniel Cunningham’s portraits captures the quiet intensity of a young woman.
Daniel Cunningham draws inspiration from the world around him, and is determined to perfect his craft and make his mark as a portrait artist in Kingston.
Daniel Cunningham draws inspiration from the world around him, and is determined to perfect his craft and make his mark as a portrait artist in Kingston.
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After leaving his graveyard shift, Daniel Cunningham doesn't head straight home to rest.

Instead, the 24-year-old trades his bed for a sketchbook, roaming the busy streets of Half-Way Tree, St Andrew, quietly searching for a face willing to pause long enough to be drawn.

The Kingston native is an untrained portrait artist, fuelled less by formal training and more by raw passion and determination to sharpen a gift he believes can one day sustain him.

"Sometimes mi tired, yes, but mi still go same way because mi know mi want turn this into a real business and an extra income," he told THE STAR.

Portrait drawing, one of the oldest forms of visual art, demands patience, observation and a deep understanding of human features. From capturing the curve of a jaw to the subtle emotion in a person's eyes, portrait artists rely on skill honed through constant practice.

"Mi used to practise on friends, but coming out here is my way of pushing myself out of mi comfort zone, and showing people what mi can do," he said.

In a strange way, the sidewalk has become the classroom for a man who started drawing when he was in primary school.

"I would just sit down and look at things and try to draw it back," he recalled.

But high school distractions pushed the pencils aside until about two years ago.

Though rejection is frequent in Half-Way Tree, it has not shaken his resolve to turn his talent into a viable business. He describes himself proudly as an up-and-coming portrait artist, even while acknowledging that his academic journey did not follow a traditional path. He didn't get any Caribbean Secondary Education Certificate (CSEC) passes at high school, and although he did some City & Guilds exams, he did not go back for the results.

It is a chapter of his life he does not shy away from, but one he is determined to move beyond. Like many young men, he admitted that he became distracted by peer pressure and the desire to fit in.

"I was able to go to school but I was never focused. I was following the crowd and tried to be somebody cool and tried to fit in with everybody else," Cunningham said.

With maturity, his perspective has shifted, and he now sees his father's guidance in a different light.

"Him always try and encourage me and mi think him miserable, but as mi grow and see how adult life stay, mi wish me did listen and be more focused in school."

Art, however, has been a quiet constant in his life.

"I've been working since I left school selling things, construction, and now I do security services for a small company but I started drawing again and I want to become better at it."

Armed with pencils and paper, he now takes his work directly to the public, offering to do portraits in hopes of building both skill and visibility.

"Mi come pon the road and showcase my work and offer my services to draw people. Mi get mostly rejection from people weh mi try show mi work on the road. Sometimes dem a move pon rush or some just not interested."

Despite the setbacks, Cunningham sees every interaction as an opportunity to improve. Payment, he says, is secondary to practice and growth.

"I still try to do it even if I am not getting paid because that gives me practice. I want people to be able to look at a drawing and just know it's me do it."

He studies other artists closely, particularly a portrait artist from Portmore whose ability he deeply admires.

"Him so skilled, him can just see you one time and capture the features and draw. Mi still have to look at pictures and it takes time."

Looking ahead, Cunningham hopes to return to school to formalise his skills and lay the foundation for a sustainable art business.

"I know people will pay for things they love," he said of his passion for art.

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