When I was just a teenager, my mother and I were at a garage sale and found the most fantastic piece of art I have ever seen. We bought it for the typical garage sale price – cheap – and later found it had extraordinary value. This work of art is one of the original, authenticated Highwaymen paintings.

The Florida Highwaymen are one of my favorite groups of artists. This group of 26 African-American artists began in the early 1950’s and continued creating their art through the 1980’s. Their paintings are beautiful landscapes of Florida.

This group began under Alfred Hair, the original Florida Highwayman. His mentor in the early 1950’s was an artist by the name of A.E. “Bean” Backus. Mr. Backus taught Alfred to paint landscapes. Soon after, Alfred realized he could make money for his works of art. He encouraged his friends to begin painting as well.

The Highwaymen knew that because of the times, and the color of their skin, making a living off these paintings was going to have to require them to stand out amongst the crowd. The way they did this was by painting in their garages or backyards on very inexpensive Upson or Masonite boards. Then on the weekends, they would travel all around the area selling their art to places like hotels, offices, and the occasional individual for around $25 per painting.

The Florida Highwaymen gained their infamy in the 1990’s when “outsider art” became popular. Jim Fitch, the first journalist to write about these 26 artists, gave them the name the Florida Highwaymen because of their strategy to drive up and down I-95 to sell their artwork. Shortly after, the New York Times picked up this topic. Since then, several books have been written about the group.

Fourteen years ago, the original 26 artists were inducted into the Florida Artists Hall of Fame. Some of their paintings are being sold for up to $19,000 today. It’s my honor and privilege to have to opportunity to call one of these original 26 a friend, Al Black.