Florida Highwaymen Paintings

Have you ever heard of the Florida Highwaymen Artists? Chances are that if you have ever lived in Florida, then you either know about the Highwaymen painters or seen one of their paintings. If you aren’t from Florida you may be missing out on an interesting group of gifted painters.

The Florida Highwaymen were a loosely affilitated group of blacks, all but one were men, who specialized in painting colorful landscapes of Florida. The landscape paintings were popular for a few reasons: they were inexpensive, appealed to tourists and looked good in the new homes of the growing Florida market.  

The Florida highwaymen sold their paintings along the highways of Florida, hence their name. These artists knew that they could not compete with pricing their art in the realm of other known artists at the time. Instead, they believed that they could actually make more money buy selling a lot of paintings at low prices, rather than selling one painting at an expensive price. They figured that they could make up the difference by selling in quantities. It was not unusual for the artists to paint 5 or 10 pieces a day. The art was often sold out of the trunks of their vehicles.  Many times the artwork was still wet, as it did not have enough time to properly dry.

To help keep costs down, the Highwaymen Paintings were not painted on traditional artist canvas. Instead, the paintings were created on the back of building materials. A wallboard masonite type product called Upson board, was used in place of the canvas. The paintings were secured in Picture frames that were created from crown molding. It was a lot cheaper to create the frame from the molding rather than use a store bought or gallery frame. 

There were approximately 26 people in this loosely knit group of artists. Some of the artists didn’t even know each other because some had left the group while newer artists joined later. These paintings were created and sold mostly during the 1950s, 60s and 70s. Some of the original Highwaymen Artists still paint today.  There’s even Second Generation Highwaymen and also Highwaymen Styles Artists of every background and race who have carried on the tradition. You can still purchase Florida Highwaymen paintings in Florida and they can be purchased at galleries, yard sales and websites.  The thing that people loved about the artwork is that it was affordable and appealed to the new homeowners and tourists alike.  Who couldn’t afford $10.00 or $25.00 for an original piece of art?  It was attainable for all and it looked great on the wall.

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