What sets the Highwaymen apart is not just their artistic talent, but also the unique circumstances under which they worked. In an era of segregation and limited opportunities for African Americans, these artists found a way to make a living by selling their artwork directly to the public. They traveled along highways, hence the name “Highwaymen,” selling their paintings from the trunks of their cars or along the side of the road. This entrepreneurial spirit allowed them to bypass the traditional gallery system and connect directly with buyers.

While the Highwaymen initially faced challenges due to racial discrimination and the lack of recognition from the mainstream art world, their work eventually gained widespread acclaim. Today, their paintings are highly sought after by collectors and enthusiasts alike, and they are recognized as an important part of Florida’s cultural heritage.