The Florida Highwaymen — Artistic and Entrepreneurial Success

Pigment International
5 min readJan 26, 2021


From Pigment Magazine

Creativity in the arts can emerge from the most unlikely of places. What some consider the last great American Art Movement of the 20th century emerged from southeast Florida at the hands of itinerant, self-taught African-American artists.

The movement emerged from the rural segregated Jim Crow south. Presented with limited social and economic opportunities in the 1960s, Blacks sought opportunities wherever they could. Refusing to be defined by agricultural labor, low wages and the constraints of racial segregation, they fought mightily to expand their prospects. In Florida, most Blacks were destined to have lives filled with “planting, picking, and packing,” the group of artists destined to become the Highwaymen were determined to break through this cycle and make a living doing something else — creating art.

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The unofficial leader of the group was Alfred Hair. Hair, a resident of Fort Pierce, was a good student and athlete. His art teacher, Ms. Zenobia Jefferson, recognized his artistic gifts and introduced him to his future mentor, Alfred E. Backus, a white artist. Hair enrolled in college, but left after two years. Back home, he honed his skills and won recognition for his art. It is debated how much “art” he learned from Backus, but it is certain Backus planted the idea and provided a living example that he could make a living from art. All of the artists in the collective displayed varying degrees of artistic talent at early ages, but art making was no more than an interesting hobby until they made and sold their creations.

Hair was not satisfied with accolades. His art was always a means to an end. Above all, Hair wanted to live the “good life” — money in his pocket, fast cars and an active social life. Hair was determined to make a lifethrough art. This spirit was infused throughout the group.

The market for Florida landscape paintings was a solid one. Floridians were proud of their locale and wished to see it reflected on their walls. In the 1960s, Jim Fitch, a marketer, coined the term ‘Highwaymen’ for the collective based on the fact that they sold paintings along east coast of Florida along US 1 from Fort Pierce to Daytona Beach ostensibly “out of the trunks of their cars.” This was not entirely true, but was effective.

The Highwaymen artists stuck to the established conventions of Florida landscape art. They emphasized the interface between land and water — especially rivers, streams swamps, mangroves, beaches, thickets, and lagoons. The unique flora of Florida was highlighted — Poinciana and Cypress trees, live oaks, palms, Spanish Moss and wild orchids. Fauna was not usually depicted with the exception of birds. Birds were featured in in a majority of works. Atmospherics played an outsize role in many of the depictions. Bright blue skies with the occasional puffy clouds and bright orange sunsets were a staple in a number of images. By combining these elements, the images displayed a spiritual reverence for the landscape. The Florida of the imagination was a place of idyllic, unspoiled nature that needed capturing before it “disappeared.”

Work by Florida Highwayman Al Black, Jr.

At its zenith, the Highwaymen grew to 24 men and one woman They were self-taught, but firmly familiar with the norms of landscape art. Their works usually possessed a dominant horizontal orientation. Light was used very specifically to allow the viewer to accurately discern the time of day and the season of the year. Nature was faithfully rendered in realistic colors. Florida landscapes were very volatile when changing weather was considered. Images often reflected the weather’s influence highlighting the tenuous and transitory nature of Florida’s environments. Overall, their techniques resulted in images that were emotionally evocative and compelling. Hair perfected his plan to make his living creating art. His economic model was quite different from the Backus approach. Backus had gallery representation and commissioned sales to rely upon. He made art slowly as in one piece per week. His price points were high ($200 to $500 per piece).

Conversely, the Highwaymen adopted a different economic model, employing an assembly line approach to maximize their output. They worked fast, frequently making 5–10 pieces per day. To further minimize costs, they used economical materials — Upson boards replaced Backus’s canvases and crown molding was used for framing. And, in addition to production, they were their own sales force, engaging in direct selling to their customers They priced their works, on average, at under $50. The quality of the paintings was good, and the prices were competitive in the extreme, well under the prices of comparable gallery landscapes. Collectors were offered a high-value product.

Salesmanship was an integral part of their approach. A quote attributed to Highwayman Al Black was “A painting isn’t finished until it’s sold.” Value triumphed over racial stereotypes.

Interest in acquiring works by the Highwaymen remains high today. Determining the value of individual works can be a fraught exercise. The basis of valuation depends on the individual artist. Alfred Hair, Harold Newton, Al Black, Jr., and Mary Ann Carroll (the sole female member) command higher prices. Image size is a factor, and in this case, bigger is better.

Signatures are important when authenticity is in question. Condition is a significant factor because these paintings were not made for the long haul — paint loss, flaking, foxing, water spots, dirt, etc. must be considered. We also should keep in mind that some of the earlier paintings are decades old. As always, market forces and both the local economy and general economy play roles in valuing the works. Overall, the value of the artistic output of this group of artists has held up well, and paintings which were sold below $100 are now commanding prices in the five-figure range, with especially fine exemplars going for six figures. Relatives of the original Highwaymen painted in the tradition and style of the originals. Some writers include these later artists in the lineage of the Highwaymen.

Black artists painting Florida landscapes and selling them directly to the white public in the age of segregation was an inherently transgressive act. The “artistic space,” if you will, was decidedly a white domain. Today, we speak of identity politics as a bad thing; however, historically, when Black people did anything they could not, even for a minute, forget that they were Black. The fact that the Highwaymen could compete successfully, both artistically and economically, was a testament to their ingenuity, creativity and organizational and entrepreneurial skills.

Calming, pleasant and recreating a pristine, unspoiled view of nature — the images created by the Highwaymen are treasures that fit into a wide variety of settings. They have received widespread attention, certainly in Florida, but they are appreciated by collectors across the country.

Article by Dr. Michael Butler, owner of Griot Gallery, Miami, Fl.



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