Though bound by their distinct artistic style, the Highwaymen are a diverse group of people.

For some, like Ft. Pierce resident James Gibson, painting was – and still is – a sole source of income.

“I just wanted to make an honest living,” he says.

2 men and painting

Photo by Karen Laughter
James Gibson (left) and Roy McClendon are among
the Florida Highwayman who were elected to the
Florida Artists Hall of Fame in March 2004.

Gibson’s interest in art began at an early age. In grade school, he would sketch Western comic books and sell them to the other students for 5 or 10 cents a piece – a profit he used for ice cream money.

He sold his first painting to a dentist in Ft. Pierce for $20. Gibson, then a student at Tennessee State in Nashville, was home for the summer. A week later, he returned to the same dentist and sold two more, for $25 and $30.

“I was a real artist then,” he says with a laugh. “After I sold that third painting, I didn’t want to go back to college.”

And he didn’t need to. That was 1959. For the next 30 years he hit the road, driving from Miami to Jacksonville and everywhere in between, selling his paintings for about $30.

“We wore our shoes out and tore up cars,” Gibson says. Sometimes he didn’t have enough gas in his car and money in his pocket to make the return trip, so he would count on selling a painting to make it back home.

“I always believed I could sell a painting,” he says. Mary Anne Carroll, the only female of the group, was similar to Gibson in her reliance on painting for income. A mother of seven whose husband left when her youngest was five years old, Carroll took to the highway because the flexible schedule allowed her to spend time with her children.

As “a woman surviving in a man’s world,” Carroll faced unique challenges. Fortunately, she says, “I could fight as well as I could paint.”

Sometimes she would travel with fellow Highwaymen to sell her paintings; other times, she would venture alone into cities and towns that were not always accepting of black people.“It was a challenge because I either had to be brave or be afraid.”

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