Highwaymen History

History of the Florida Highwaymen

In the segregated world of 1950s Florida, not many opportunities were available for African American artists. Unable to show their work in galleries, which were typically “whites only” venues for both customers and artists, Black artists had few options for marketing and selling their work. The group of artists who came to be known as the Florida Highwaymen painters found themselves creating opportunities where there were few, and in the process created a new style of art – and a new style of selling art – that earned these artists a place in history.

Alfred Hair Painting Miami Herald 1962
Alfred Hair finishing a landscape painting, Miami Herald, Dec 19, 1962

Today’s Highwaymen experts, most notably the director of Florida’s Museum of Art and Culture, Jim Fitch, and author and professor, Gary Moore, name Alfred Hair and Harold Newton as the artists who served as the driving force behind the collective effort that defined the Highwaymen. Both talented artists in their own rights, it was a successful local white painter, A.E. “Bean” Backus, who encouraged and mentored Hair and Newton in their work. Under Backus’ guidance, Newton moved away from the portraits and religious scenes he had painted and sold within his community in Gifford, Fla., and began focusing on landscapes. It was Zanobia Jefferson, an art teacher at Lincoln Park Academy in Fort Pierce, Fla. who played an influential role in the lives of several of the Highwaymen painters, who introduced Hair to Backus in the early 50s. Under Backus’ formal training (Hair was the only Highwaymen painter to receive formal training from Backus, although Backus informally mentored several of the young painters), Hair also began to focus on painting landscapes.

Both Newton, working in Gifford, and Hair, working in Fort Pierce, knew there was a market for their works and took it upon themselves to find it. Hair began striking out on his own to sell his work from the trunk of his car (possibly following Newton’s lead of taking his work out on the road, but this remains unclear), heading up and down the east coast of Florida and stopping in at professional and medical offices, banks, and other businesses to show and sell his work. He quickly was selling as many as 50 paintings a week and earning a considerable amount of money for the time – enough to buy himself a Cadillac. To keep up with demand, Hair began working in what he called his “fast style” of painting, working on his paintings in an almost assembly-line fashion with 20 to 30 canvases propped up around his home and yard, methodically and quickly moving from one to the next as he filled in foreground, mid-ground, and background, skies, waterways, and vibrant landscapes for each unique work.  

Florida Highwaymen Alfred Hair painting, ca. 1965, Smithsonian
Orange Sky, Breaking Surf, 3 Birds by Alfred Hair (1941 – 1970), ca. 1965, Smithsonian Museum

“He had the game plan, the vision and the business sense to monetize his creative talents,” notes Marshall Adams, executive director of the Backus Museum and Gallery told Indian River Magazine. “Undoubtedly, he could have painted slower, but he decided to streamline many aspects of Backus’ paintings. His critical review was whether people bought them or not.”

Word soon spread of Hair’s enterprise and an ever-growing circle of friends and family joined him, some assisting him with his paintings, others painting on their own, and still others devoting themselves to building frames for the artists and taking on the role of salesmen.  

Florida Highwaymen Al Black paints several paintings outside
Highwaymen artist Al Black works outside on several landscape paintings

“It was like spontaneous combustion,” Gary Monroe told the New York Times in 2019. “Alfred encouraged and welcomed all who had an inkling or expressed an interest in painting. There was no organization, no rules, dues or business plan — just like-minded 20-somethings coming together.”

Florida Highwaymen artist Harold Newton painting in his backyard
Harold Newton painting in his backyard in Florida

Meanwhile in Gifford, Newton was experiencing a similar level of success. Following Backus’ advice to focus on landscape painting, Newton, like Hair, had quickly realized there was demand for his romantic Florida landscape paintings and began selling them on the road, door-to-door to medical and legal offices, retail stores, banks, and any other venue in the market for of-the-moment Florida décor. Newton has been credited with creating the modus operandi of what became known as the Highwaymen movement, but it is unclear whether he or Hair first began selling their paintings from their cars or if perhaps it was an idea the two materialized together as they worked under Backus’ mentorship. Unlike Hair, however, Newton was a slow and exacting painter and kept his production to a staid (for a Highwaymen painter) four paintings a day. As Gary Moore put it in a 2007 blog post for Art and Antiques Around Florida, “The bottom-line concerning Harold Newton’s productivity was the one offered by his brother, Lemuel Newton, who told me, ‘There’s got to be a lot of ‘em.’”

Florida Highwaymen brothers Harold and Lemuel Newton
Highwaymen brothers Harold and Lemuel Newton

The groups of artists working in Fort Pierce and Gifford continued to grow, and decades later Gary Moore would identify 26 of them (25 men and one woman) as key members of the group Jim Fitch had dubbed “The Highwaymen Painters” in the mid-1990s:

List of Florida Highwaymen:

Florida Highwaymen Harold Newton Smithsonian Painting
Rough Surf Crashing Ashore by Harold Newton (1934 – 1994), ca. 1970, Smithsonian Museum

The Florida Highwaymen painters painted consistently from the mid-1950s until the early 1970s when tastes began to change and the market for colorful Florida landscapes waned. The murder of Alfred Hair in 1970 had also left the Fort Pierce painters without his leadership and talent, and they eventually moved on to new careers, or continued to paint on their own. It would be nearly thirty years before Jim Fitch and Gary Moore’s enthusiasm for these Floridian landscapes would revive interest in the Highwaymen and their work.

Highwaymen Willie Reagan, Lemuel Newton, Rodney Demps and Mary Ann Carroll show off their paintings

The Highwaymen style of painting was indeed a version of Backus’ lauded landscapes but filtered through their own perceptions and experience of the natural world around them.  Gary Moore calls their work “A version of the American Dream with a tropical twist,” and describes them as intuitive painters and brilliant colorists who were, for the most part, working from observation and without academic training. “They left a visual legacy of modern Florida,” Moore says. “It’s their paintings that captured midcentury Florida – with eloquence and insight.”

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