Alfred Hair, from the Ft. Pierce area, began painting Florida landscapes in the late fifties. In 1955, at age 14, he went under the tutelage of local landscape artist A. E. “Beanie” Backus, as did other young artists. These artists developed their unique techniques, creating depictions of Florida’s sunsets, waterscapes, marshes, and inlets with raw beauty and charm. Through the leadership and creativity of Alfred Hair, the artists shunned traditional methods, and painted quick, brisk images of Florida’s tropical beauty in bright colors, often painting on wood, masonite, or a roofing material called Upson board.
Three years later in 1958, Hair left Backus to strike out on his own. Hair and the other Highwaymen sold their creations from the trunks of their cars along Florida’s east coast for as little as twenty dollars each, showering the state with approximately 200,000 paintings. On August 9, 1970, Hair was killed in a local juke joint during an argument over a woman.