Florida Highwaymen

Back in the 1960s, it was not uncommon to see people hawking paintings at the side of the road in tourist destinations. That’s a way of life that has, for the most part, died out, but Bobbi Heath and I did run into a car-trunk art gallery in Round Pond last year.

From the 1950s into the 1980s, twenty-six African-American painters from the Fort Pierce, FL area created and sold an enormous body of work from the trunks of their cars. Estimates range up to 200,000 pieces. They hawked their paintings on roadsides, thereby earning themselves the belated sobriquet, “the Florida Highwaymen.” All of this was under the radar of the art establishment, of course.

The Highwaymen were selling to newly-arrived Floridians and tourists, so they painted iconic scenes of Florida: beaches, palm trees, billowing clouds, and mossy live oaks. This not only made monetary sense; it was a safe subject for black painters in the Deep South. As most of the painters came from the Indian River region, rural Florida was imprinted in their memories.

The Highwaymen were not plein air painters, rather, they gathered together in carports, shaded yards or sheds and churned these scenes out from memory. It is unlikely that any of them had much art education, but the founders operated loosely under the mentorship of A.E. Backus, a Florida landscape painter with a genius for fostering young artists.

Harold Newton was painting religious scenes when he met Backus. Backus encouraged him to take up landscape painting instead. Newton did, and began selling his paintings door-to-door, creating the model that his peers would eventually follow. Newton worked in the traditional way, creating his own compositions and marketing them.

Meanwhile, another young man with radically different ideas had been introduced to Backus. Alfred Hair was a mercurial, charismatic teenager who quickly drew others into his orbit. His goal was never to make great art, but to make as much money, as fast, as he could. He set up an assembly line in a back lot, tacked a sample painting to a tree, and recruiting other young artists to paint. Artistic expression was never his first consideration; he and his painters were working to survive.

What were the options for the Florida Highwaymen in a Jim Crow state? Migrant farm labor was their expected path. Instead, the Highwaymen painters chose the risks and rewards of entrepreneurism.

Unfortunately, Hair’s character was his undoing; he was shot to death in a popular local bar at the age of twenty-nine. Without his leadership, his group slowly fell apart. 

The Highwaymen’s palette seems bizarrely bright to us today, but it was fashionable in mid-century, when inexpensive art flooded the country for the first time. They used oil-based paints on Upson-board, an inexpensive pressed-paper sheeting product that is thick and relatively spongy. The finished work was framed using crown moulding spray-painted silver or gold. Their goal was fast, inexpensive production. They sold the resulting art on A1A and US 1 from Daytona Beach to Miami.

As the state population boomed, some of the Highwaymen moved inland. New Floridians were eager to decorate with art that looked like their new paradise. And the Highwaymen’s paintings were very reasonable: around $25 for a nice big canvas. That’s about $215 in today’s money.