Florida Highwaymen Art

The Florida Highwaymen were a loosely affiliated group of mostly self-taught Black painters originating in the Ft. Pierce, Florida area on the state’s Atlantic coast 70 miles north of West Palm Beach. The 25 men and one woman considered the original Highwaymen painters began painting in the segregated 1950s as a preferable income earning opportunity to manual labor in the state’s citrus groves. The popularity of Florida Highwaymen art waned in the 1980s, although a few among the group continued painting well into the 2000s.

Like the Impressionists of Paris a century before, the Florida Highwaymen captured the look and feel of their surroundings in a unique, instantly recognizable style heavy on artistic flair and vivid coloring previously unseen. Their enormous collective body of work has come to define both a time – the mid to late 20th century – and a place – rural Florida – just as the Impressionists did a modernizing Paris.

How many Florida Highwaymen were there?

There are 26 artists recognized as original Florida Highwaymen. Among the group was one woman, Mary Ann Carroll. The Florida Highwaymen were never formally organized by rules, dues, membership or a business plan. What connected them was their subject matter, painting style, race, location, business model and era.

Alfred Hair was the first member of the Highwaymen. He, along with Harold Newton, are the Highwaymen’s most well recognized members. Their paintings are the most expensive of all the Highwaymen.

The 26 original Florida Highwaymen artists were elected into the Florida Artists Hall of Fame in 2004.

How many original Florida Highwaymen are still alive?

Only a handful of the original Florida Highwaymen are still alive and all are elderly. R.A. “Roy” McLendon can still be found painting almost every day from 11 AM – 3 PM at his studio/gallery inside Vintage Vero in downtown Vero Beach. He welcomes visitors.

Al Black recently completed a mural project in Gainesville.

A second generation of Highwaymen painters does exist, including Alfred Hair’s son, Kelvin.

List of Florida Highwaymen

Alfred Hair, "Untitled (Beach Scene with Palms." Oil on board, 24 x 36 inches. COURTESY OF THE LIGHTLE COLLECTION. (C) DORETHA HAIR TRUESDELL. PHOTOGRAPHY BY TARIQ GIBRAN
Alfred Hair, “Untitled (Beach Scene with Palms.” Oil on board, 24 x 36 inches. COURTESY OF THE LIGHTLE COLLECTION. (C) DORETHA HAIR TRUESDELL. PHOTOGRAPHY BY TARIQ GIBRAN

These artists are recognized as the original 26 Florida Highwaymen. Their birth dates are followed, when applicable, by the year in which they died.

Why were these artists called the Highwaymen?

The Florida Highwaymen artists were so named for the way in which they sold their art. Forbidden access to Florida’s museums and art galleries due to their race in Jim Crow Florida, The Highwaymen traveled widely around the state selling their paintings from the trunks of their car. They were especially prominent selling along Florida’s Route 1 which went from the Florida Keys in the South all the way to the Georgia state line in the North.

They’d sell paintings along roadsides.

They’d go door-to-door in neighborhoods.

They’d cold call doctors’, lawyers’ and dentists’ offices. During the 1960s and 70s, countless professional offices and hotels housed Highwaymen paintings – purchased on the cheap – as decoration.

“There were so many of these paintings along Atlantic coastal Florida, and beyond, that the imagery, I believe, seeped into viewers’ sub-consciousness and the American psyche, giving the idea of mythic Florida,” Florida Highwaymen scholar and collector Gary Monroe once told me. “Paintings hung in homes and in offices (came) to be so omnipresent… they cast their spells, they became part of the collective experience of the American dream.”

Remember, this period in Florida, the late-50s through 1980, was a period of explosive population growth for the state fueled by the space industry in Cape Canaveral, surging tourism (Walt Disney World opened in 1971), and development with Florida being an increasingly popular haven for northern retirees. All the newcomers needed something “Florida-y” to put on their walls. In the days before Michael’s and Home Goods, that meant original paintings.

Something inexpensive, colorful, easy to appreciate.

Enter the Florida Highwaymen.

What did the Florida Highwaymen paint?

Harold Newton (1934-1994), Beach Scene, undated. Oil on canvas. Vickers Collection Harn Museum
Harold Newton (1934-1994), Beach Scene, undated. Oil on canvas. Vickers Collection Harn Museum

Florida Highwaymen art shows a mid-century, rural Florida before the shopping centers, interstates, land giant communities and developers took over. They painted sunsets on beaches. Palm trees swaying in the wind. Their iconic, red poinciana tree.

Only on extremely rare occasions would a recognizable figure appear in a Highwaymen painting. As a result, those paintings have a higher value.

How did the Florida Highwaymen paint?

The Highwaymen painted with oils, applying paint “wet-on-wet,” not letting under layers dry before working over them. They did not utilize underdrawings or photographs to conjure the images captured. In fact, they didn’t paint en plein air, they worked at home from memory and imagination. 

While the Highwaymen were mostly self-taught, they received a helping hand from Florida’s premiere regionalist at the time, A.E. Backus, who provided them with some introductory pointers.

Again, due to the limitations American society placed on African Americans during the Highwaymen’s heyday, they were forced to improvise with materials. They used commonly available house paint acquired from hardware stores as opposed to the fine art oil paint sold specifically to artists. Instead of canvas, they used Upson board, a cheap building material popular at the time they could often source second-hand from construction sites for free.

The combination of the two gives Florida Highwaymen art its unique “look” – a heated up, sunburnt, Technicolor fantasy befitting the Sunshine State. There is no mistaking a Highwaymen painting.

Also critical to understanding the Highwaymen is understanding how they painted: FAST!

The Highwaymen were feeding their families through their artwork and couldn’t labor over paintings for days or weeks. They needed to sell paintings, and in order to sell paintings, they needed to paint paintings. Lots of them.

It wasn’t unusual for a Highwaymen painter to paint 20 paintings in a single day. Alfred Hair could paint 50 in a day.

Do the math: 26 painters working for 20-plus years producing that many paintings every day. Estimates place the number of original Florida Highwaymen paintings somewhere around 200,000! That’s just during their peak years from the mid-50s through mid-70s. Considering work from the original members who continue painting today and that number might double.

Florida Highwaymen art wasn’t small either. While the paintings couldn’t be so large as to not fit in the trunk of a car – remember how they were sold – Highwaymen paintings are generally in the 24 to 30-inch range, aligned horizontally, perfect for display over a couch or receptionist’s desk.

Thanks to the Orlando International Airport, there are now digital reproductions of Highwaymen paintings on view there 20-feet tall in Terminal C.

How much are Highwaymen paintings worth?

Harold Newton Untitled [ Early river scene with herons ] n.d. Oil on Upson board 25 ¾ x 20 ¾ in. Courtesy of the Asselstine Collection © Harold Newton Photography by Tariq Gibran
Harold Newton Untitled [Early river scene with herons ] n.d. Oil on Upson board 25 ¾ x 20 ¾ in. Courtesy of the Asselstine Collection © Harold Newton Photography by Tariq Gibran

Florida Highwaymen art originally sold for as little as $20. Theirs was a volume business. The Highwaymen weren’t selling to wealthy collectors, they were selling to new homeowners, retirees and small business owners. The Highwaymen weren’t trying to get rich, they were trying to get by.

It wasn’t until the later 1990s when Highwaymen paintings became considered a valued piece of Florida history and worthy of collection and display as fine art. Until then, the paintings were often acquired via yard sale for less than $50.

With some 200,000 original Highwaymen paintings having been produced, their value is not driven up by scarcity. Surely tens of thousands of the paintings have not survived, but they still don’t experience high demand from museums or public collections, they’re largely the domain of specifically interested private collectors.

An early, large, original oil painting in good condition from an original Highwayman artist painted during the peak years of the 1950s, 60s and 70s can now sell for well over $10,000. Paintings fitting that description by Alfred Hair or Harold Newton can exceed $100,000 in some instances.

On the flip side, small paintings completed after the 1980s can be purchased for about $1,000 from reputable dealers.

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