The Florida Highwaymen used vivid and bright colors in their paintings to display the beautiful untouched Florida landscape art. They painted wind-bent palm trees, serene sunsets, churning oceans and bright red Poinciana trees. This art looked great on the walls of businesses and homes.
One of the original Florida Highwayman, Alfred Hair, was introduced to a prominent white artist named A. E. "Bean" Backus in the mid 1950s. Under the direction of Mr. Backus, Alfred was encouraged to paint landscapes and realized that he could make a living doing it. Alfred encouraged several of his friends to begin painting as well, and soon the Florida Highwaymen became a sort of social group.
The Highwaymen artists knew they could make a living painting, but they knew they had to be different. Mr. Backus was a prominent white artist and could sell his paintings for hundreds of dollars in galleries and shows; no gallery would show the work of unknown, self-taught African-Americans. Instead they painted from their garages and back yards on inexpensive Upson board and then on the weekends they would travel and sell their paintings to hotels, offices, businesses and individuals who appreciated the artwork for around $25 a piece.
In the 1980s the Florida Highwaymen unofficially disbanded after consumer tastes changed. But because of a recent surge in demand for their work several of the original highwaymen have come back to painting.
In the early 1990s an interest in "outsider art" or art which is created by artists who are outside mainstream society, developed in the art world and in 1995 an article was written for a journal by Jim Fitch who coined the group the "Highwaymen" because of their tactics of traveling I-95 and A1A to sell their artwork. Not long after this the New York Times wrote a review of a documentary about the Florida Highwaymen and two books on the group have been published since then, causing the value of Florida Highwaymen art to skyrocket.
In 2004, the 26 original Florida Highwaymen were inducted into the Florida Artists Hall of Fame.
The Highwaymen are credited for encouraging the beginning of the "Indian River School" and "Backus" art movements and have many followers, but these 26 individuals are the only true "Highwaymen."
In the early 1950s through the 1980s a group of twenty-six African-American artists painted beautiful landscapes that displayed the serene, undeveloped Florida landscape of their time. Today these artists are known as the "Florida Highwaymen" and because of the tranquil scenes and history involved, their original paintings are highly demanded by collectors and enthusiasts.