by Gary Monroe

In spite of the Highwaymen’s soaring popularity during the past few years, misinformation still exists that hampers appreciating the artists and, ostensibly, the last great-untold tale of modern Florida. The basics are these: the Highwaymen were black youths from Fort Pierce, Florida, who, during the late 1950s and early '60s, taught themselves to paint Florida scenes in the manner of A.E. Backus, an established white artist of the time. They sold their framed oils from the trunks of their cars, mainly along the state’s east coast.

Highwaymen Painting by Livingston Roberts
24 X 36 inches, oil on canvas. Livingston Roberts. Courtesy of Henry Bosma.

In September of 1998, wanting to learn more, I met with Mary Ann Carroll (the only female of the group), James Gibson and Hezekiah Baker. I was amazed by their stories. Newsletter articles about the Highwaymen didn’t jibe with what I was hearing so I embarked on finding out what happened to give rise to their 100,000 plus paintings and what it might mean. I subsequently identified and interviewed all but a few of the artists (three are deceased, some have moved away). I count twenty six Highwaymen, who are listed and discussed in my book.
Contrary to the accepted myth that claims their paintings were pieced together by uncaring hands, by bird, water and tree “specialists,” the artists, according to Roy McLendon, each “painted their own pictures.” This is corroborated by the others. And, there was never a school or movement. These artists didn’t even have studios. They worked in their backyards “like shade-tree mechanics,” offers Mary Ann. In fact, there really were no Highwaymen.... just an amorphous group of friends who found an alternative to toiling in the nearby fields and packing houses.
The Highwaymen is a moniker that Jim Fitch, a promoter who is fascinated by what he calls Florida’s Art Tradition, assigned to the group in 1994. He often came across Highwaymen paintings — in thrift stores, yard sales, and the like — and recognizedthat something special had happened. The newly bestowed name ruffled some feathers but folks seem to have accepted that it was the perfect choice to get the ball rolling. To a few people the name conjured images of stagecoach robbers while to others it was met with resistance because it wasn’t their choice. Perhaps fair claims, but Jim’s instincts catapulted interest in the story and the paintings.

Alfred Hair - Highwaymen Painting
24 X 36 inches, oil on Upson board. Alfred Hair. Courtesy Mr. & Mrs. Geoff Cook

Jim's primary concern was not the Highwaymen aesthetic, which is central to mine, but commerce. It would be naive to think about the Highwaymen solely as artists. Their modus operandi was about making money. Alfred Hair knew it wasn’t likely he’d gain the acceptance or have the success Backus enjoyed. (Hair was the only painter of the group trained by Backus.) So, instead of charging a price in accord with a Backus canvas, of say $250, he opted to charge $25 and make up for the “shortfall” with quantity. He made ten paintings in less time than it took Backus to complete a single painting. Speed yielded a new style. “Fast painting” led to the distinguishing characteristics of their art, which the Highwaymen arrived at by corrupting the classical pictorial strategies Backus so well incorporated.
Since making money, not art, was their goal, the Highwaymen needed to shower the state with their paintings. And they did! The artists often got together to paint through the night. These were good times. It wasn’t unusual for an artist to make ten, even twenty, paintings at a stretch. James Gibson told me Alfred had lifted weights to be able to paint without tiring. James challenged himself to make a hundred paintings in a twenty four hour marathon. His ubiquitous two color landscapes resulted.

Highwayman, A.E. "Bean" Backus - "Glades Glory"20 x 24 inches oil on canvas, "Glades Glory," 1970. A.E. "Bean" Backus. Painting compliments of the A.E. Backus Gallery & Museum, Ft. Pierce, Florida (C). Included here to illustrate the influence Backus had on this group of painters.

To maximize profits, the artists painted on inexpensive Upson boards, a roofer’s sheeting product. The quarter-inch 4' x 8' sheets were easily cut into waste-free sizes, typically four 2' x 3' pieces (the Highwaymen’s signature size) with the remaining piece cut in some combination of 2' x 3', 12 ”x 24” and 18” x 24” or left as is, 2' x 4'. The boards were shellacked, painted on, and sold before the oils had time to dry.
Since the artists rushed, flaws were not unusual. I saw a Mary Ann Carroll seascape on which (presumably) her bright yellow fingerprint floated in an equally bright blue sky. Nor is it unusual to see smudged paintings. Highwaymen frames were constructed from crown molding that was designed as door, window and floorboard trim. At nine cents a foot it was more practical than buying frame molding strips. The standard sizes facilitated stacking the paintings for transport but occasionally paintings would bump and smudge. Al Black, who entered the Highwaymen as a salesman, says that he “learnt [to paint] by fixing them.” A painting wasn’t finished until it was sold.
Al Black said “Alfred could paint as good as he wanted and as fast as he wanted.” He preferred his production mode. The artists played a kind of game in which money was the way to keep score. Alfred wanted to be a millionaire by his thirty fifth birthday and having a Cadillac was his interim goal. All those painters who wanted the status-symbol car had them. So they had to paint fast and paint a lot! With “wads of dough” in their pockets, everything was going better than planned. But, in 1970, Alfred was murdered. He was twenty nine years old. We originally were told he took a stray bullet in a barroom brawl. In fact, he was shot at close range over a woman. He left six children and a cottage industry which defined a time and place.
Business remained brisk. The artists prevailed during the '70s, selling their paintings "door to door and store to store." Shop owners and professionals were their best customers. There were lots of empty walls to fill. Prices were set by calculating the daily pay of a blue-collar worker. The larger paintings, at $25 or $35, weren’t necessarily cheap, but they were affordable, and, to many, irresistible. Curtis Arnett points out, “People waited for us to come by.”
The Highwaymen’s facile process yielded images that seem to be lingering memories from having glanced at an expanse of land through the window of a vacation bound car. In this way, to sojourners, Florida-in-passing looked sketchy, half realized — ripe for people to lend their own meanings. The transitory nature of Highwaymen imagery yielded an intimacy that would be lost to a more formal treatment.

24 X 36 inches, oil on masonite. H. Newton. Courtesy Tyson Trading Co.

The images by artists of the Hudson River School, that a century before gave rise to the tradition of landscape painting in America, carried near-religious significance. Such imagery sanctifies one’s beliefs: Backus addressed the congregation while the Highwaymen looked for converts, so to speak. Backus had the knack, with his pink cotton candy clouds and brilliant juxtapositions of color, to make those of us who are so susceptible weak in the knees. Highwaymen paintings appealed to people who didn’t ordinarily buy art. Their images engaged people who looked to the Sunshine State as the place to realize the American Dream.
Perhaps their picture-window paintings didn’t celebrate unspoiled nature as much as they reflected the consumers’ values and aspirations. In that the heyday of the Highwaymen coincided with the settling of contemporary Florida, these paintings commemorated the homesteading of the region and, by extension, the state. Now, having served their purpose, as banners proclaiming one’s arrival, the paintings have been dusted off, reconsidered and commodified. In Florida today, there is a near-feeding frenzy over acquiring Highwaymen paintings, and, like the potato chip commercial suggests, it seems that nobody can have just one.
The resurgent popularity of Highwaymen paintings is, I believe, in part, a reprieve from our technologically driven and often alienating society. Even “art snobs” have found virtue in what some detractors have called “motel art.” I find the pejorative referent uplifting; the paintings “document” wondrously the culture that gave rise to them. One needn’t be apologetic. A non traditional sensibility may be required to appreciate Highwaymen paintings, but, after all, aren’t fresh eyes necessary for artists to make relevant observations?

24 X 36 inches, oil on Upson board. M.A. Carrol. Courtesy Mr. & Mrs. Tim Jacobs

Some collectors have amassed hundreds of paintings and intelligible collections. One cites being compelled by a “been there, seen that” feeling. The sentiment about capturing real Florida is commonly expressed. I hear reports about enthusiastic first-time buyers as well; each excited by the proposition of connecting with a Highwaymen image. Highwayman Willie Reagan told me the old days were fun and profitable.... it looks like they are still.
The unspoiled landscape the pictures represent and slower times they suggest may provide solace as we wipe mildew from the furniture, tolerate increasing traffic on the roads and rude soccer parents on the sidelines. Or perhaps acquiring a painting provides solace because at the heart of the images are disenfranchised blacks who had suffered through "Jim Crow" Florida and escaped their own bleak destinies. Nevertheless, there is more to the paintings than meets the eye.


THE HIGHWAYMEN: Florida's African-American Landscape Painters by Gary Monroe.

This book sets the facts straight and will add legitimacy to the already popular works of this unique group of artists. Published by the University Press of Florida.

About the author:
About the author:
Gary Monroe authored the primary Highwaymen books. These, as well as his other books about Florida art and culture may be viewed on his Website, along with his photography, at

Antiques & Art Around Florida
The Best Antiques Guide Magazine in the U.S.!

[Top of Page | Editorial Articles | Home]