The Journey of the Highwaymen

 by Catherine M. Enns, Abrams

Al Black’s Concrete Dreams

 by Gary Monroe, University Press of Florida

The Highwaymen: Florida’s Outsider Artists


Striving young African Americans in 1950s Jim Crow Florida, which is not exactly flowering with opportunities, decide to become self-trained artists. Since galleries are white only, they hawk their stuff themselves. And against the odds, they make it work. Now two lavishly illustrated new books and an hour-long documentary reveal the surprising twists and turns on their road to success. The Indian River Folk Art School, as the Highwaymen are formally called, ironically starts with a white painter, A.E. Backus, who loves his native state’s vanishing flora and fauna and Claude Monet’s art. He trains a young black man named Alfred Hair, who organizes the Highwaymen. Working assembly line fashion, they learn to create art cheaply. Then they sell it door-to-door and from car trunks along roads like U.S. 1, where motorists gawk, pull over and buy. For a decade they make money and somewhere between 100,000 and 200,000 landscapes, most suffused with brilliant, quasiCaribbean colors. Painted on inexpensive materials like Masonite, the paintings are often stacked to dry so quickly that some bear faint imprints of others. The whole operation is classic American do-it-yourself bootstrapping. Take Al Black: He starts in the biz as an ace salesman and learns to paint from retouching landscapes loaded into his car when wet. Imprisoned on drug charges after the Highwaymen’s glory days, he paints 100 murals for the Department of Corrections. Finally, in 2004, the Highwaymen are “rediscovered” and inducted into the Florida Artists Hall of Fame. Today the survivors are painting and marketing almost as aggressively as in their heyday.


Originally published in the December 2009 issue of American History. To subscribe, click here.