Folk Art

Essay - The Highwaymen: Fast Times, Fast Painting

Gary Monroe

The Highwaymen were black youths from Fort Pierce who, during the late 1950s and early 60s, taught themselves to paint Florida scenes that served as picture-windows overlooking an idealized landscape, a place where dreams would come true. They sold their framed oils from the trunks of their cars, mainly along the state’s East Coast. A fertile market existed for affordable and original art about Florida as families established themselves during the post-war boom.

The Highwaymen’s story was little more than a rumor when, in 1998, I met with Mary Ann Carroll, James Gibson, and Hezekiah Baker. The few existing accounts about the Highwaymen didn’t jibe with what these artists were telling me. For example, contrary to the accepted myth that claimed their paintings were pieced together by uncaring hands, by bird, water and tree “specialists” each contributing to the production of a single painting, each artist painted their own pictures. 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.

The unfolding story was intriguing, ready-made and ripe for the telling. It needed only a sympathetic intermediary, and, as a native Floridian and an image-maker myself, I fit the bill. Although their story needed no embellishment, I continued to encounter misinformation about the group’s artistic practices. So I embarked on finding out what happened to give rise to their prodigious output of paintings and what it might mean.

The Highwaymen, during their day, were a loose and nameless association of twenty-five men and one woman who seemed more likely to toil in the citrus fields near to where they grew up than to become the visual artists of their time and place; the ones to, albeit inadvertently, leave a testimonial in the form of perhaps 200,000 oil paintings that would be the marker for the tropical version of the American dream.

Their story begins in the late 1950s, when Alfred Hair took painting lessons from A. E. Backus, a prominent white regionalist. Florida’s tropical beauty provided Backus ample inspiration; his time-tested aesthetic yielded paradisiacal images. Owning a Backus’ canvas was tantamount to claiming the land. But young Alfred read the images differently; to him they provided another kind of inspiration – a means to escape a bleak future and become wealthy.

As he graduated from high school, Alfred left the artist’s studio and gathered a few of his friends. He offered them – figuratively, as no one could have predicted what would follow – an opportunity to rise above social expectations, the remedial inferiority to which African Americans were relegated. By teaching them the conventional painting formulas that he had learned, he gave the others a way out of “Blacktown.” Their enterprise went strong for twenty-five years, until the culture shifted and tastes changed.

The Highwaymen moniker was assigned to the group in 1995, shortly after the paintings came to light in thrift stores, yard sales, and flea markets. People recognized that something special had happened. Early admirers of the Highwaymen were primarily concerned not with their aesthetic, which is central to my interest, but with commerce. Indeed the painters’ modus operandi was about making money. The paradox of the story is the compatibility, if not the mutual dependence, of art and commerce. Money was not a corrupting influence in this story.

Alfred devised a system to mass-produce paintings and thereby be able to sell them relatively cheaply. This involved working on multiple boards – developing certain areas in phases – to minimize labor and material, and hence maximum profits. Each artist was able to complete a group of paintings during their customary nightlong painting fests. He and his cohort developed a fresh form of landscape painting by shedding the established modes in favor of mass production.

The quickness with which the core group painted altered the classical pictorial strategies that Backus, like other academic artists, incorporated. The Highwaymen arrived at their connotational style by necessity – time meant money. Hair’s fast painting led to the distinguishing characteristics of the Highwaymen’s art. Their facile process yielded images that seem to be lingering memories from having glanced at an expanse of land through the side window of a vacation bound car. Florida-in-passing looked sketchy, half realized and ripe for people to lend their own meanings.

Instead of charging a price in accord with a Backus canvas, of say   two-hundred-and-fifty dollars, Hair opted to charge twenty-five dollars for one of his own paintings and make ten paintings in less time than it took Backus to complete a single painting, and hence earn the same money. One might fairly reason that the Highwaymen’s haste would have resulted in inferior paintings. Ironically though, the speed – their painting in the moment – freed these artists, letting them paint responsively, and, like a wellspring, their intuitions flow.

Harold Newton, the story’s other progenitor, painted in the manner of Backus, rivaling the esteemed artist, in fact. Newton painted with more contemplation and greater formal resolve than the others. But he still painted fast – applying paint wet-on-wet with deft skill bordering on magical – and he sold his paintings on the streets. Newton was the polar opposite of Hair and the prototype for him. He epitomized the artists’ ideal, making glowing, exemplary images that seemed to form themselves effortlessly.

The painters were “transparent,” not wanting to draw attention to themselves as they traversed the state offering their wares for sale. This wasn’t primarily because they generally (almost always) did business without having occupational licenses. Rather the focus had to remain on the interests of the viewers: The gestural nature of the images only conveyed a sense of place. Removed from its context, the landscape’s significance was rendered mysterious, ephemeral and up for grabs – just like Florida itself at that time.

The transitory nature of their imagery offered an intimacy that would have been lost to a more formal treatment. The inability of the image to confirm narrative left a void that compelled each viewer to interpret the land pictured for him or her self. Viewers were co-authors, “finishing” the pictures in their own minds. And given the paintings’ varied symbols, sublime beauty, and willing collaborators, ascribing meaning was irresistible. So powerful was the draw that buyers personalized generic scenes with confidence. The river bend was inevitably the spot where this bass was caught or that place on the St. Johns where….

Since making money, not art, was their goal, the Highwaymen needed to shower the state with paintings. And they did. It wasn’t unusual for an artist to make ten, even twenty, paintings at a stretch. The Highwaymen’s hybrid landscapes each took as little time as half an hour to complete; seldom did they spend much more than an hour on a painting.

Highwaymen Al Black observed, “Alfred could paint as good as he wanted and as fast as he wanted.” He preferred his production mode. Alfred was driven, determined to be a millionaire by his thirty-fifth birthday. He had to paint fast and paint a lot! To the Highwaymen, a painting wasn’t finished until it was sold. No painting was sold dry. With “wads of dough” in their pockets, everything was going better than planned.

Alfred Hair may have acquired the wealth he desired. Cash rolled in and he, and other painters, sported the high life. But just shy of being thirty-years-old and on top of the world, Alfred took a bullet in an argument, which barely involved him, that escalated over a woman while cavorting in a juke joint. He died later that night at the Ft. Pierce Memorial Hospital. He succeeded in forming the unlikely atelier that was responsible for the creation of Florida’s visual legacy.

The artists prevailed during the 70s. Shop owners and professionals were among their best customers. They approached people in their offices to take advantage of multiple sales. Calculating the daily pay of a middle-class worker set prices. The paintings weren’t necessarily cheap, but at twenty-five dollars they were affordable, and, to many, irresistible. Curtis Arnett points out, “People waited for us to come by.” They unfailingly showed up on paydays.

The Highwaymen’s customers were people who didn’t generally purchase art; people that, from all accounts, didn’t know much about art but knew what they liked. And the Highwaymen’s paintings were perfectly suited for them. The Highwaymen arrived at the archetypes of the landscape by stripping bare the artifice that distinguished traditional landscape painting; the approach that objectified the land, yielding it foreign to the people who flocked to Florida then. The artists’ imagery was as fanciful as it was realistic; enticing enough to sanctify the consumers’ beliefs. The images engaged people to look at the Sunshine State as Paradise attainable.

Maybe the Highwaymen’s picture-window paintings didn’t celebrate unspoiled nature as much as they reflected the consumers’ aspirations. Their paintings were made for folks wanting assurance, not those desiring high art. In that their heyday coincided with the settling of contemporary Florida, these paintings commemorated the homesteading of the region and the state. By extension, the paintings acknowledged the broader ethos that established Florida as Eden. Now, after decades of dormancy, having served their purpose as banners proclaiming one’s arrival, the paintings have been dusted off, reconsidered and commoditized.

The resurgent popularity of Highwaymen paintings is, in part, a reprieve from our technologically driven and often alienating society: The ancient wilderness is viewed with increased enthusiasm as the land gets bulldozed out of existence. The presence of the land so painted transcends change and all it brings – fast-food restaurants, strip malls, traffic jams, and the threat of terror.

The slower times that the paintings suggest may offer stability as we face our uncertain post-World Trade Center future. Or perhaps these paintings provide solace because at the heart of the images are disenfranchised blacks who had suffered through "Jim Crow" Florida and escaped their own bleak destinies. There’s satisfaction seeing the oppressed prevail. Nevertheless, there is more to these paintings than meets the eye.

This article first appeared in the Spring 2003 issue of the American Folk Art Museum's "Folk Art" magazine and was adapted by the author for inclusion in the Florida Humanities Council's "Forum" magazine a year later.

Back to Essays



Back to The Highwaymen