Text by: Dr Michael Butler

Artistic creativity in the arts emerges in the most unlikely 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 southern racial hierarchy based on white supremacy and maintained by coercion and violence made the South increasingly hostile for Blacks. In the 1950s the modern Civil Rights era was in its infancy, but the battle lines were drawn. This South was contested terrain. The 1954 Brown Vs. the Board Supreme Court decision outlawed segregation in schools. The Montgomery Bus Boycott ruling outlawed segregation in public transportation. Lunch counter sit-ins in Tennessee and North Carolina opposed segregation in restaurants. Throughout the South segregation was under siege. Blacks were hopeful, but their immediate prospects for advancement were dim.

Survival was the first priority. The 2nd “Great Migration” continued North and West—any place, but here. Migrants were pushed by southern violence and the strict Jim Crow codes and pulled by job opportunities and less restrictive living arrangements. “Down Home” Blacks were determined to change their prospects by moving. The urge to migrate was compelling, however, everyone did not have that option. How could they change their fortunes while remaining in the South? Many sought opportunities by moving from rural areas to urban areas. This “migrate in place” strategy provided some relief from day labor, tenant farming and sharecropping arrangements and marginally improved their economic status.

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AL BLACK, JR., Untitled Lower Right , Oil on Board, 25 1/4 x 37 1/4 in. 1975

Blacks In The Groves

Central Florida is the heart of the orange growing industry in the United States. Orange harvesting was and still is very labor intensive. Oranges have to be picked at a precise time. This particular task even now cannot be relegated to machines. Oranges that are not ripe when picked, never ripen once they are removed from the trees. Workers, in 90+degree heat, climb 6 ft. ladders, pick the fruit, place the fruit in sacks that are emptied into carts and then off-loaded to trucks. Workers were paid by the pound: .03-.05 cents/lb. The work was only available seasonally from May to September. The other common jobs open to Blacks, day laborers and domestic service workers, were paying slightly lower wages about $20/week than they could earn in grove jobs. All available occupations were challenging. This was the fate for blacks in Central Florida during the era of segregation. Working conditions created a precarious hand to mouth existence that was nearly inescapable.

Nevertheless, Blacks in the South dreamed of a better lifestyle and desired work that was respected, stable, and that offered a chance to prosper. Stuck in the rural Jim Crow south and presented with limited social and economic choices, Blacks searched for options everywhere. Refusing to be defined by agricultural labor, low wages, and the constraints of racial segregation, they fought to expand their prospects. In Central Florida most Blacks were destined to lives of “planting, picking, and packing.” From this milieu the group that was to become the “Highwaymen” formed. Desperate to prosper, these Black Floridians used their creativity to make a living and a life, doing something else. They would create art.

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ISAAC KNIGHT, Untitled Lower Right, Oil on Board, 8 x 10 in

A Collective Based On Entrepreneurship

Artist collectives have formed to advance aesthetic considerations, engage socially, or promote a specific political agenda. However, an artist association based on entrepreneurship was unique.

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AL HAIR, Untitled Lower Right, Oil on Board, 24 x 48 in. circa 1970s

Beginnings – Harold Newton and Alfred Hair

Harold Newton

Harold Newton was the first of the Highwaymen to meet Alfred E. “Bean” Backus—a white artist. This meeting was one year before Backus was introduced to Alfred Hair. Harold Newton met “Bean” in the early 1950s. He brought work to be critiqued and received limited instruction. Backus noted that Newton had an almost photographic memory and outsized talent. Newton could look at a Backus piece, leave for a couple of hours, and return having created an almost flawless copy.

Backus influenced Newton to change the subject matter from Biblical images to Florida Landscapes. Before he returned to Florida, Newton lived in Georgia and sold Biblical images “door to door”. However, outside the Bible Belt “Velvet Jesus” was a non-starter. Floridians had little interest. When Newton changed subjects, switching to Florida landscapes, his art sold. He maintained his sales technique of selling his art directly to the public in a door-to-door fashion and this direct sales method was at the core of the Highwaymen’s entrepreneurial success.

Alfred Hair

Before the “group”, there was Alfred Hair. Hair, a resident of Fort Pierce, was a good student, artist and athlete. His art teacher, Ms. Zanobia (sic) Jefferson, recognized his artistic gifts and introduced him to future mentor Backus. Hair enrolled in college for two years, but left for financial reasons. Returning home, he continued to hone his artistic skills and over time gained recognition for his art. It is debatable how much “art” Alfred learned from Backus, but what is certain is that Backus planted the idea that you could make a living doing art and provided Hair with a living example of a “not starving” artist. Friends of Hair emulated his example and with differing degrees of talent and commitment decided to give art a try. Most of the artists in this circle of friends displayed artistic talent at early ages, but art making was no more than an interesting hobby. All that would change when they sold their work.

Alfred came to be seen as the unofficial leader of the group. There were no votes, but the artists gravitated toward him and consented implicitly to his leadership.

Unsatisfied with accolades, Alfred and his crew wanted money. Their art was always a means to an end. All wanted to live the “good life”— money in their pockets, fast cars, and active social lives. The friends were determined to reap tangible benefits from art. This was definitely not art for art’s sake.

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WILLIE DANIELS, Untitled–Florida Backwoods Sunset Lower Right, Oil on Canvas 16 x 20 in.

Regional Changes and the Art Market

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. Tourists visiting Florida wanted to have a tangible reminder of their vacation.

In this era, Florida was rapidly transforming. Disneyworld was established in central Florida in 1960s, highways were crossing in every direction, and NASA was a growing presence. Finding idyllic, unspoiled nature was becoming difficult and elusive. The tranquil settings people associated with Florida were being displaced by development. “Old Florida” resided only in memory and imagination. Both Backus and the Highwaymen tried to capture the “Florida look and feel” before it “totally disappeared.”

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AL BLACK, JR. Backwater Scene Lower Right, Oil on Masonite 20 x 24 in

Backus and The Highwaymen: A Study in Contrasts

Though Backus was a successful artist, by adopting or imitating his processes and practices, the group would be doomed to failure. Innovation and modification were the secret ingredients to their success. Some of the significant ideas that were implemented had origins beyond Al Hair. Hair however combined them to maximum benefit.

Backus encouraged the artists to use economical materials such as Upson board, instead of canvasses, and crown molding, instead of traditional frames. Backus used these materials when he was first starting.

Hair developed a painting technique where the landscape features were suggested in the images, but required the viewers to engage (“connect the dots”) and “furnish” the details. The net result was he could make art fast. To further increase speed, Hair occasionally used an assembly line approach. In his backyard “studio”, he would nail several boards to trees and work simultaneously on them. Hair’s “associates” would paint the background and horizon lines and he would fill-in what would become the completed image. Hair would also paint a single color on all his paintings at once–all the blues, all the greens, etc. This was a technique that Jacob Lawrence used for most of his series work.

To maximize his painting time and produce more work, he hired salesmen to sell the works. He kept painting while someone else was out on the road selling. The “Newton” direct sales model aligned with Hair’s technical innovations was quite different from the Backus approach. By combining several elements, Hair perfected his plan to make his living creating art.

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CHARLES “CHICO” WHEELER, Untitled–River Inlet with Boat House Lower Left, Oil on Board, 14 x 11 in.

Backus and The Highwaymen: A Contrast In Strategies

Backus Highwaymen
Themes and SubjectsFlorida Landscapes Florida Landscapes
Memory and Imagination
Memory and Imagination
VenuesGalleryDoor to Door
Store to Store
Working EnvironmentSolitaryCommunal
Material ChoicesStretched Canvas
Traditional Framing
Upson Board and Standard Sizes
Crown Molding
1 painting per day
5-10 paintings per day
ProcessSingle—One At A TimeMultiples—Several At Once

Themes and Subjects

The Highwaymen were self-taught, but firmly familiar with the look of Florida landscape art. 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. Landscapes reflected the very volatile, changing weather that Florida frequently experienced. Images highlighting the weather’s constantly evolving, tenuous and transitory nature resulted in art that was evocative and compelling.

The Highwaymen artists interpreted the Florida landscape and developed their own unique depictions of it. The interface between land and water—especially rivers, streams swamps, mangroves, beaches, thickets, and lagoons was emphasized. The unique flora of Florida—Poinciana and Cypress trees, Live Oaks, Palms, Spanish Moss and Wild Orchids was highlighted. Fauna was not usually depicted with the exception of birds that are featured in a majority of works. Few scenes had people or manmade structures.

Atmospherics were essential to the paintings. Bright blue skies with the occasional puffy clouds and bright orange sunsets, “fireskies”, were a staple in Highwaymen images. Taken together, these elements, displayed a spiritual reverence and respect for the landscape.

Being white, Bean had an unrestricted access to the properties that he would later paint. Bean painted the landscape he saw. The Highwaymen in contrast had limited access to those properties and often had to paint from photographs. Backus kept a book of images to show clients for their commissions. Frequently the Highwaymen artists drew inspiration from those scenes.

Other artists who painted Florida landscapes in the styles similar to Backus and the Highwaymen were collectively known as the Indian River School.

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CHARLES “CHICO” WHEELER, Untitled–Florida Night Indian River Lower Left, Oil on Board, 20 x 28 in.


Backus had gallery representation and could rely on commissioned sales. Waiting lists, months long, were his norm. People knew him as the Dean of Florida Landscape Artists and actively sought him for commissioned works. In the age of segregation, Black artists were not allowed to exhibit in galleries.

Until their resurgence in the 1990s, the Highwaymen were barely known. With time, their images were actively sought, but with few exceptions a particular artist was not important to the clients. In most cases, the authorship was minimally important to the artist. Images were what sold. Some would sign their name to the others’ works and that was generally accepted. What ultimately mattered to them was getting paid.

Backus’s studio and gallery sales sharply contrasted with Hair and friends who did not know their clients by name (at first) in most instances. Frequently visiting lawyers’ offices, doctors’ offices, motels, and restaurants, they engaged the proprietors directly with their sales pitch. Businesses, however, looked forward to the artist coming by especially on return visits and subsequently developed client relationships.

Sales Strategy

The sales force Hair hired to directly sell to customers was an integral part of their strategy. A quote attributed to Al Black was “A painting isn’t finished until it’s sold.”

As with image making, some were gifted artists. Likewise with sales, some were gifted salesmen. Al Black Jr., a former typewriter salesman was a master salesman. Al could sell ice to an Eskimo. As the lead salesperson, Al would load up his trunk with 10—20 paintings, venture into towns and stops along A1A and US1 visiting businesses, and always come back with his trunk empty. This was a very bold, brave undertaking in the time of Jim Crow. Black movement was severely scrutinized and constrained especially when Blacks appeared in what was perceived to be white spaces.

Besides being a master salesman, Al Black was a master in putting white people at ease. He knew just how to approach them in an unctuous, non-threatening manner.

Later Al became an artist in his own right. During transport, the art would sometimes be damaged. Determined to not hold up a sale, Al frequently painted over the damage to sell the works. Ultimately by observation, imitation, and practice. Al painted.

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TRACY NEWTON, Untitled–Stormy Ocean Scene with Palms, Lower Right, Oil on Board, 12 x 24 in.


Backus priced his art in the multi-hundred dollar range and for the times those price points were high ($200 to $500 per piece). Because of his celebrity, Backus’s work could command such high prices.

Less well known, the Highwaymen commanded much lower prices. By pricing all of their works under $50, they filled a market niche with art that the public perceived as a good value. Good quality, high value, and competitive prices were a combination that led to impulse buying on the part of the customer and led to prosperity for the artists.


Backus painted in a naturalistic style that limited the speed of his production. Committed to capturing nature in a realistic manner required him to focus on fine details. This was a slow process allowing him, on average, to complete one piece per day.

Because of his clients-in-waiting and the prices he could command, speed was not a problem. He lived by all accounts frugally and was financially secure if not rich.

For the Highwaymen this was not acceptable. They wanted big, fast money. Constrained by price, elected to do volume. Volume could not be generated without speed. They worked fast frequently making 5-10+ pieces per day. This was possible by modifying their techniques, work specialization, and creating multiple works simultaneously.

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AL BLACK, JR. Untitled (Indian River Inlet Scene at Sunset with Docked Boat) Lower Right, Oil On Board, 16 x 20 in.

Choice of Materials

To minimize costs they used economical materials—Upson boards and crown molding. The boards also came in sizes where they could be cut with minimal wastage. This generated one of the most popular sizes for their paintings—24 X 36 inches.

The crown molding provided some protection for the art, because it allowed the paintings to stack easily in the car trunks, giving space to art that was frequently shipped out before the paint was dry and at increased risk for gouging or smudging.

In addition, the customers liked the framing because the art would be ready to hang.

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AL BLACK, JR. Untitled (Indian River Inlet with Fishing Boat), Oil on Board, 18 x 24 in.

Working Environment

The loosely affiliated group was more like its Black Cultural counterpart—a quilting bee. Bees were occasions where seamstresses would get together and make “squares” that they would collectively assemble to make a quilt. That atmosphere was like a social event rather than a work assignment. The artists first and foremost were a circle of friends with social gatherings that resulted sometimes in working together, going to Jai Alai or the dog tracks, or “holding court” in their local bar.

Unfortunately their social life led to tragedy. Getting into a bar fight, Al Hair was shot and killed at the age of 29. This almost killed the group before they would become the Highwaymen. Activity slowed down and sales dropped. The artists continued to paint, but it was not the same without Alfred.

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ISAAC KNIGHT, Untitled–Yellow Fire Sky, Lower Right, Oil on Canvas, 24 x 30 in.

The Name—Highwaymen

In the 1960s, Jim Fitch, a marketer, art investor and gallery owner, coined the term Highwaymen for the collective based on the fact that they sold paintings on the east coast of Florida along US 1 and A1A from Fort Pierce to Daytona Beach and south to Miami ostensibly “out of the trunks of their cars.” This was not entirely true, but it was effective marketing. The artists were not initially sold on the name, because of its prior association with highway robbers and bandits. Some artists wanted to be considered as individuals rather than a member of any group. However, this name sparked a resurgence, renaissance, and renewed the public’s interest in their art. Though uncomfortable, the artists realized the name’s value had given them a second life. They swallowed hard.

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AL BLACK, JR. Untitled, Lower Right, Oil on Board, 24 x 36 in.

The Highwaymen Market Today

The interest in acquiring works by the Highwaymen remains high. Ultimately the group grew to 25 men and one woman. 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., Willie Daniels, James Gibson, Roy McLendon, Sam Newton, Livingston Roberts and Mary Ann Carroll (the sole female member) command higher prices, because they are considered the “Core 9” and instrumental to the “movement”.

Some Highwaymen possessed superior technical skills that are displayed in many of their works and as a result some see these works as more valuable.

Image size is a factor and in this case bigger is better. Signatures are important when authenticity is in question.

Condition may be a significant factor because these paintings were not made for the long haul—paint loss, flaking, foxing, water spots, dirt, etc. should be considered. Many of the original frames are damaged, but collectors try and keep them. We also should keep in mind that some of the earlier paintings are decades old.

As always market forces, both the local and the general economy play roles. Overall the value of the artistic output of this group of artist has held up well. Paintings that were sold below $100 are commanding prices in the four and five figure range with especially fine exemplars going for six figures.

Estimates suggest that the Highwaymen completed over a 100,000 paintings. How many of those numbers that exist today is speculative. By pricing and construction, the paintings were essentially disposable.

Relatives of the original Highwaymen paint in the tradition and style of the original group. The Original members mentored most of these associates. Some writers include these later artists in the lineage of the Highwaymen based on their kinship and association. This second generation are adhering closely to their legacy are stimulating interest.

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AL HAIR, Untitled–Indian River Scene with Palm Trees On Verso, Oil on Board, 24 x 36 in.

Interracial Collaboration Across the Tracks

Avenue D was the center of commercial activity and the heart of the Black community in “Colored Town” in Fort Pierce. Avenue C, a few blocks away separated by railroad tracks, was a white neighborhood. When it came to Black and white interaction, that short distance would be unbridgeable. The exception was the home of “Bean” Backus. His Avenue C home was a combination salon, school, and studio. Bean welcomed any and all no matter their race. His home was the nexus of good conversation, good music and discussions about the topics of the day. He taught, guided, and encouraged any would be art students. Frequently he provided space for artists to paint under his observant and watchful eye where those artists were rewarded with gentle supportive critiques. His support for the artists extended to materials and supplies, loans, etc. Bean’s place, on occasion, would turn into a supper club with food and drink freely available.

The support, guidance, and friendship of Alfred E. Backus cannot be overstated. Backus a true altruist and mentor to many, especially in the arts community, who has to be given credit for the flowering of the Highwaymen. Fostering and teaching along the way and providing a safe space for Black artists to interact with whites, take lessons, etc. cannot be overemphasized.

Black artists painting Florida landscapes and selling them directly to the white public in the age of segregation was an inherently transgressive act. Black artists interacting with whites was also a transgressive act. “Artistic Space” was one that was decidedly white. We speak of identity politics as a bad thing, however, 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.

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FREDDIE GIBSON, Untitled–Florida River Scene with Palms, Lower Right, Oil on Board, 35 1/2 x 19 1/2 in.


In the 1990s, and beyond, in large measure the group became know as the highwaymen. The public took a second look at their artistic production and discerned that they were true artists that had a unique vision of the vanishing ideal of Florida landscape. In 1993, the original Highwaymen and Highwaywoman were inducted into the Florida Artists Hall of Fame. The works commanded exponentially higher prices and were included in many celebrity collections including Michelle and Barack Obama.

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SAM NEWTON, Untitled, Lower Right, Oil on Board, 25 x 36 in. circa 1970s


Many of the artists are still painting and own galleries. Some achieved college degrees and became educators. Some trained a second generation of Highwaymen. Several became pastors.

Some went to jail, but still painted and persevered. Al Black deserves special mention. During his prison stint he painted the only known murals by a Highwayman.

Calming, pleasant and recreating a pristine, unspoiled view of nature, these images are treasures that fit into a wide variety of settings and are welcomed into the homes and businesses of Florida and throughout the world.

The Florida Highwaymen’s story of artistic and entrepreneurial innovation is a quintessential American story of achieving success by making a way out of no way.

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CHARLES “CHICO” WHEELER, Untitled–Sunset Scene, Lower Right, Oil on Board, 18 x 24 in.

A Note About Titles and Dates

The Highwaymen did not title many of their works nor date them. They did not live with their paintings long enough to title them in most instances. Catherine M. Enns in her book, The Journey of the Florida Highwaymen, developed a classification scheme to address the lack of titles by classifying their works by subject matter. She has 13 categories:

  1. Royal Poinciana
  2. Ocean Shore
  3. Breaking Waves
  4. Fireskies
  5. Indian Diver
  6. St. Lucie and Inland Rivers
  7. Back Country
  8. Back Country Pines
  9. Rivers of Grass
  10. People
  11. Stormy Weather
  12. Moonlight On the Water
  13. Orange Groves and Rarities

The plates in her book are grouped into these categories and she provides numerous examples.

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ROBERT L. LEWIS, Untitled (Two Birds), Lower Left Verso signed on Verso Robert L. Lewis. Oil on Board, 4 1/2 x 6 1/2 in.



  1. Enns, Catherine M., The Journey of the Highwaymen, New York, NY,: Harry N. Abrams Publishers, 2009
  2. Butler, Robert and Munoz, Dr. Sheila R., Highwaymen—An Untold Truth—44th Anniversary 2nd Edition, CreateSpace Independent Publishing, 2012
  3. Monroe, Gary, The Highwaymen Murals—Al Black’s Concrete Dreams, Gainesville, FL: University of Florida Press, 2009
  4. Monroe, Gary, Harold Newton—The Original Highwayman, Gainesville, Fl : University Press of Florida, 2007
  5. Monroe, Gary, The Highwaymen—Florida’s African—American Landscape Painters, Gainesville, Fl : University Press of Florida, 2001


  1. Alfred Hair and the Florida Highwaymen—Landscape Artists, Florida Department of State
  2. Fitch, Jim, The Highwaymen, Antiques & Art Around Florida, Winter/Spring 1995
  3. Lyden, Jackie, Florida’s Highwaymen Painted Idealized Landscapes in Jim Crow South, NPR—WLRN 91.3, All Things Considered, August 10, 2013
  4. Bucknell, Alice, How Florida’s Black “Highwaymen” Painters Made a Living in the Jim Crow South, Artsy.net, Feb 15, 2018
  5. Lyden, Jackie, The Landscape Art Legacy of Florida’s Highwaymen, NPR—WLRN 91.3, All Things Considered, September 19, 2012
  6. Authentic Florida, The Highwaymen: Florida’s African American Artists Who Defied the Odds, February 5, 2018
  7. The Florida Bookshelf, Florida Highwaymen: A History. October 16, 2014
  8. Angell, L. L., Painter Is Adding to Highwaymen Legacy, Vero Beach Newsweekly, August 19, 2015
  9. Monroe, Gary, The Highwaymen Phenomenon, Antiques & Art Around Florida, Summer Fall 2001
  10. Hurd, Gordon K., Alfred Hair: 1942–1970, Overlooked—New York Times, 2019
  11. Florida’s First Highway Men, Gadsden Arts Center, 2017