Florida’s Highwaymen Defied Jim Crow Law With Their Art

Although they were shut out of Florida’s museums and galleries in the 1950s, 26 Black painters captured Florida’s tropical landscapes and managed to make a living—and a name for themselves—off their art.

Florida’s Highwaymen Defied Jim Crow Law With Their Art

“After the Storm” was created by Harold Newton, one of the founding members of the Highwaymen.

Courtesy of the Lightle Collection

When you think of Florida, what comes to mind? Just the mention of the state might conjure images of palm trees on sandy beaches and fronds rustling in a gentle breeze. Seagulls, sailboats, and sunsets the color of ripe citrus. Rust-red poinciana trees that wouldn’t look out of place in a fairy tale. It’s a quintessential tropical paradise that really only exists in the imagination—and in the paintings of Florida’s legendary Highwaymen.

The Florida Highwaymen were a group of 26 Black landscape painters who lived and worked in and around Fort Pierce, a coastal town 136 miles north of Miami. They weren’t a formal association, but rather, a circle of friends and acquaintances who inspired one another and were united in their mission to make and sell art. They almost never worked observationally (that is, they didn’t paint reality), instead composing their pieces from memory to capture the dreamy, tropical essence of the state. Between the 1950s and 1970s, the Highwaymen—which eventually included one woman, Mary Ann Carroll—produced more than 200,000 paintings, most of which weren’t dated, titled, or formally inventoried in any way.

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‘Spanish Bayonets’ by A.E. ‘Bean’ Backus. He’s credited with both influencing and helping the Highwaymen.

Courtesy of the A.E. Backus Museum

Their story begins in 1955, when 21-year-old Harold Newton, then specializing in religious art, visited regionalist painter A.E. “Bean” Backus at his home studio in Fort Pierce. Backus encouraged Newton to stop painting scenes from the Bible and instead focus on what was around him: Florida. Newton, who was almost instantly taken with Backus’s artistic style, made the switch. At that time—nearly a decade before the Civil Rights Act of 1964 and the Voting Rights Act of 1965—Black Americans living in the Jim Crow South were barred from displaying their art in museums and galleries. So, Newton began selling landscapes on his bicycle along Highway 1, a busy stretch of road packed with businesses like motels, realty agencies, law firms, and doctors’ offices.

Newton continued to paint and sell, peddling his paintings and inspiring a few other local artists with his technique. But it wasn’t until the early 1960s that what is now the signature Highwaymen style took off. In 1958, Backus took another painter under his wing: the prodigiously talented 14-year-old Alfred Hair, introduced to Backus by one of Hair’s high school teachers. For three years, Backus mentored Hair, who went on to pioneer the fast and resourceful techniques that became a hallmark of the Highwaymen’s art.

To keep costs down, Hair used Upson board, an inexpensive construction material similar to drywall, instead of canvas. He would then frame his pictures with crown molding, also to cut costs. And instead of working on just one painting at a time, Hair would work on dozens, even inventing a makeshift, assembly line–style easel in the process. He would work so fast, in fact, that the paintings he sold were often still wet.

Newton and Hair, who became friends, made a big impression on other local Black painters, who saw their success and were inspired to pick up their own paintbrushes. Hair’s fast-painting techniques helped artists produce large volumes of art quickly, while Newton inspired them to sell paintings out of the trunks of their cars—hence, the Highwaymen.

But, of course, the Highwaymen needed an audience—and it came in the form of a staggering population boom. Prior to World War II, Florida’s population hovered around 1.8 million residents (a bit less than that of Arkansas). By 1960, that number had doubled due to combination of factors, including state-wide real estate speculation targeting northern retirees, NASA employees relocating to Cape Canaveral to aid in the Space Race, and, naturally, tourism.

These were the days before mass-reproduced art, and those millions of new Florida residents needed something to hang over the couch. A newcomer could buy a 48-inch-wide picture of a blissful sunset, perfect for the living room, from a Highwayman for $20, or about $182 by today’s standards. Since they were so inexpensive, the Highwaymen’s art made it into many hotels around the state, and tourists often bought a painting or two to take back home with them.

However, navigating Jim Crow laws as a Black artist in Florida—which doled out some of the toughest punishments on record in the country—was no walk in the park. Luckily, the Highwaymen had a little help from Hair’s mentor, Backus, who was well-established in the art world (and also happened to be white). As the Highwaymen grew in numbers, Backus—a native of Fort Pierce who studied at the Parsons School of Design in New York City—advocated for the painters, often offering them constructive criticism, buying them art supplies whenever they needed it, and letting them sleep at his studio if they needed a place to stay.

“This was a time during Jim Crow where African American individuals were expected not to go in the front door,” says J. Marshall Adams, executive director of the A.E. Backus Museum and Gallery. “They were expected to go in through the back door. Backus was completely different. He expected [everyone] to come to his front door.”

The Highwaymen operated successfully throughout Florida well into the 1970s, but interest soon began to wane. In 1970, Hair was murdered in a barroom brawl. Known for his big personality and even bigger ambitions (he believed his art could make him a millionaire), Hair had been a key figure in the movement, and his untimely death shocked the Fort Pierce community and had a chilling effect on the group. Some of the Highwaymen even went on hiatus to mourn his passing. Then, in the ’80s, the state’s cities expanded and modern art took over. Art deco, sleek cars, and linen jackets à la Miami Vice reigned. Idyllic pictures of sandy beach sunsets were cast aside.

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The Highwaymen’s art can still be found in everyday places in Florida, such as the Ocean Grill in Vero Beach.

Photo by Chadd Scott

The Highwaymen never really recovered, but many kept painting. Newton enjoyed many years of artistic success until he died at age 59 from complications of a stroke. Caroll, the only woman of the group, lived in obscurity for most of her life but was recognized for her work at Michelle Obama’s First Lady’s Luncheon in 2011, where she presented one of her tableaus to the former First Lady.

However, you can still find evidence of the group’s legacy from places like the historic, seaside Ocean Grill in Vero Beach, where Highwaymen art hangs on the walls, to the permanent collection of the Smithsonian’s National Museum of African American History and Culture or Florida’s Artists Hall of Fame. And there is at least one original Highwayman who’s still creating art.

The legend lives on

Most days between 11 a.m. and 3 p.m., you can find R.A. “Roy” McLendon hunched over a canvas in his small, air-conditioned studio and gallery in the Vintage Vero building in downtown Vero Beach, Florida. His hands may shake, but his eyes are still “pretty good,” especially after he had his cataracts removed, he says. McLendon is one of the last living original Florida Highwaymen.

McLendon was born in 1932 in Georgia and grew up in a family of migrant farm workers with 13 siblings. In 1946 the McLendons moved to Delray Beach, Florida, and made a living picking beans for a dollar a day. As a child, McLendon loved drawing and would often use a stick to sketch pictures in the sand. “I used to draw on the ground when I was little and wait until my brothers came home from school and show it to them,” he says.

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Roy McLendon is one of the last remaining original Highwaymen. He still tries to paint every day.

Photo by Chadd Scott

When he was 18, McLendon decided to strike out on his own and relocated to Miami for a while before finally settling in Gifford, a small community near Fort Pierce. In 1955, he met Newton, and like other Highwaymen, was inspired to try his hand at selling his art to supplement his income. McLendon is best known as the “storyteller” of the group because his compositions often also include people, rather than just pure landscape.

These days, whenever McClendon makes a public appearance at a museum or show, it’s almost a certainty that his friend and fan Roger Lightle drove him there.

“I look at [Roy], I look at his paintings. They are a reflection of who he is,” says Lightle, an avid collector of Highwaymen art. He has amassed an encyclopedic knowledge of the group and a collection of about 500 Highwaymen paintings, which he displays at his Vero Beach home and gallery. “I can kind of understand who he is based on the painting itself.”

McLendon, however, has no use for conversations about legacy and reflects on his past works with an air of pure pragmatism. To him, the most important painting is the one currently on his easel. “All I did was paint and sell,” he says. “I don’t even have any paintings of mine in my home. I always had a job working [in construction] because I had a family—I’d work and paint. It was tough. I had to do what I had to do—I just love to paint.”

While McLendon might not think about his legacy, his artistic impact is living on through his sons, Roy Jr. and Ray, both painters who focus on Florida’s landscapes, just like their father. Ray has a studio and gallery of his own two blocks from his father’s, Florida Highwaymen Landscape Art Gallery. Roy Jr. can sometimes be found displaying his work at festivals and shows throughout the state. And though they might not sell art out of the trunks of their cars, Roy Jr. and Ray are keeping the memory (and legacy) of the Highwaymen alive through their paintings—candy-colored Florida skies and all.

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