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Florida Highwaymen capture unspoiled views

From the 1950s-1980s, a group of African-American visual artists, aka the Florida Highwaymen, created original art and peddled it along the highways.

Why the Florida Highwaymen are important

Florida highwaymen, Sam Newton

Florida highwaymen, Sam Newton (b. 1948) oil painting on board. Sunny beach scene with lush green palm trees and a brown picket in the sand leading into the bright blue water. Signed lower right. Board: 24” x 18”, frame: 27” x 21”. Up for bids Dec. 15 at Manor Auctions; starting bid $300. Photo courtesy Manor Auctions, Tallahassee, Florida.

Until at least the 1970s, gallery exhibitions by African-American visual artists were virtually unknown outside a slender handful of the nation’s largest cities. But that didn’t prevent black artists from producing and selling work. One of the most outstanding examples of entrepreneurial creativity came from a group of two dozen African-American landscape artists dubbed the Florida Highwaymen. They produced prolifically – over 200,000 works by one estimate – from the 1950s through the 1980s. They didn’t call themselves by any name during their peak years but were given the Florida Highwaymen moniker by journalists in the 1990s who brought them to wider attention.

The Highwaymen were loosely organized if organized at all. Some claim that Alfred Hair (1941-1970) was their leader. Likely he was less leader than mentor to some of the artists in the group. Hair was one of the only Highwaymen with some formal training, having been instructed and encouraged by a local white artist, A.E. Backus. Hair encouraged his friends and colleagues to seek a living by selling their art despite the barriers of color and class that kept their work out of galleries until years after his death.

Luscious art from inexpensive materials

The Highwaymen – and there was one woman among them, Mary Ann Carroll (1940-present) – often went door-to-door in their hometown of Fort Pierce, Florida, selling art to home owners and businesses the way others sold encyclopedias or brushes in those days. Some Highwaymen ventured out of town and sold paintings from the trunks of their cars along the state highways – a practice that later earned the group its name.

Of necessity, they painted on inexpensive materials, especially Upson and construction boards. For studios, they used their own backyards and garages when they weren’t painting plein air. Their subject matter was usually the lusciously muggy Florida landscape, still largely unspoiled by suburban sprawl and painted in vivid sunset hues.

Helping one another

Livingston Roberts (American, 1941-2004), oil on board

Livingston Roberts (American, 1941-2004), oil on board, lush green Florida water landscape at dusk. Pink sky with sun reflecting off the water. Birds fishing. Signed L. Roberts lower right; wood frame. Board: 30 x 24”, frame: 26” x 32”. Up for bids Dec. 15 at Manor Auctions; starting bid $600. Photo courtesy Manor Auctions, Tallahassee, Florida.

Curtis Arnett, born in 1950 and one of the youngest of the Highwaymen, became interested in art at an early age, sketching favorite comic book characters and dabbling in watercolor. When Alfred Hair visited his school to demonstrate art-making using oil paints, Arnett switched his medium to paint, at first scavenging left over paint cans from construction sites and painting on boards.

After stumbling upon the studio of Backus, who gave the young Arnett paint in tubes, a palette knife and a few brushes, he sought guidance from other artists including Highwayman Hezekiah Baker (1940-2007) who became his mentor.

Concentrating like the other Highwaymen on imagery from the Florida landscape, he favored cypress trees and swamps. Arnett began peddling his work on the Florida highways, stopping at local businesses offering a deal to all comers. He sold them for whatever he could, $10, $25, whatever the market would bear. 

Florida Highwaymen art values

Since those days, the value of his paintings has risen. At auction, his works range from $1,200-$2,000.

James Gibson (1938-2017) Highwaymen painting

James Gibson (1938-2017) Highwaymen painting of a Florida woods scene with yellow sunrise. Thick palette work on canvas. Signed lower right. Sight: 30” x 24”; frame 34” x 28”. On Dec. 1, this painting sold for $1,600 against an estimate of $1,000-$1,500 at Vero Beach Auction, Vero Beach, Florida.Photo courtesy Vero Beach Auction, Vero Beach, Florida.

All of the 26 Highwaymen are listed in sales index data bases where auction results for their works are recorded. In the past two years results for all of them have been favorable, with an average price range from $500 to several thousand dollars per work.

Mary Ann Carroll, known as the first lady of the Highwaymen, was one of the few of the group who had a car back in the 1960s and would sometimes bring several of the artists with her on road trips to sell their works. Fellow Highwayman Harold Newton (1934-1994) showed Carroll, already interested in drawing at an early age, how to mix oil paints when she was 16, which brought out the urge to paint. Afterward she began painting day and night to perfect her skill. In early years she earned as much as $75 per painting. Nowadays at auction, her works can fetch $2,500-$4,000.

Carroll has been honored elsewhere than in galleries and auction houses. In 2011 she was invited to Washington D.C. where she presented one of her paintings to First Lady Michelle Obama at a Congressional Club luncheon.

Robert Butler wildlife

Not all Highwaymen painted trees. Robert Butler (1943-2014) developed a style atypical of the Highwaymen. More prone to depicting the wildlife than the plant life of Florida, many of his paintings feature deer, wolves, wild hogs and turkeys, perhaps influenced by his interest in hunting rabbits and deer when he was a child. In 1970 his work was exhibited at the Polk Museum in Lakeland, Florida which gained him exposure as an artist; clients followed. After spending decades on the road peddling his work his reputation grew further; he turned to printmaking and he eventually opened his own gallery in Lakeland.

What the future holds

Some of the Highwaymen continued to paint into the 21st century and interest continues to rise.

Earlier this year, several record sales were listed. Hair’s landscape painting had a pre-sale estimate of $3,000-$5,000 at the July sale at Burchard Galleries in St. Petersburg, Florida. Titled Landscape Painting With Poinciana and 3 Black Figures, the 24” x 48” oil on Upson board hit the hammer at $23,000.

Burchard also featured four of Newton’s works at the gallery’s April 22, 2018 auction. A street scene with a mother walking her child sold for $24,000; another oil, Scene With Figure in Courtyard fetched $34,000; a third work, Street Scene With Multiple Figures climbed to $46,000 before the hammer fell. The fourth work, a coastal view with palm trees sold for $2,900.

Learn more about the Florida Highwaymen

Several books have been written on the Highwaymen as a group with one devoted to Mary Ann Carroll plus two memoirs coauthored by Robert Butler. The Highwaymen’s story of rising above adversity to triumph is worthy of a Hollywood screenplay and at one point, a movie was on the way. A trailer to a picture based on the lives of several of the artists, called The Highwaymen [], has been online for the past several years. Alas, the project appears to be stalled in development.

The Highwaymen - a Stars North film from Stars North Films on Vimeo.

Recently I stumbled across a landscape painting featuring the distinctive bright red Poinciana tree signed N. Wright. Checking the name in the database, the artist Norman Edward Wright is listed as Second Generation Florida Highwaymen, a title which suggests the story continues. is a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for sites to earn advertising fees by advertising and linking to and affiliated websites.