Being an artist is rarely seen as a ticket to prosperity and social mobility. But for Florida’s historical “Highwaymen”—a group of around two dozen black painters who made a living selling their landscape paintings out of car trunks in the Jim Crow South—art was something of a pathway to freedom.

From the 1950s through the ’70s, the Highwaymen produced over 200,000 paintings of Florida’s diverse ecology—vivid scenes depicting fiery red sunsets over aquamarine bays or the scraggy, Spanish moss-covered banyan trees stretching over the state’s backwater regions. Hawking their work straight from their car trunks, the group sold paintings to day-tripping tourists along U.S. Route 1 on Florida’s Atlantic Coast and to (predominantly white) business owners in the banks, motels, and laundromats of their native Fort Pierce, even as galleries turned them away.

The paintings originally went for $25 or $30 each, and were typically sold on the same day they were made, transported in bundles by car or bike in handmade frames and often still glistening with wet oil paint. Today, paintings by the Highwaymen are included in the Smithsonian Collection; they can clear $10,000 at auction or in private sales; and originals by the group’s most prominent figures, Al Black, Alfred Hair, and Harold Newton—who is estimated to have made over 30,000 paintings alone—are coveted by a diverse fan base that includes the Obamas and Steven Spielberg.