Essay - The Highwaymen’s Visions of Paradise

Gary Monroe

The Highwaymen – nameless until a few years ago – were African-Americans who, as youths, they seemed destined to pick oranges in the groves near their Ft. Pierce homes. But instead they taught themselves to paint and established a cottage industry that made Florida landscapes. From the mid fifties into the eighties they rushed out their distinctive scenics and peddled these from the backs of their cars along the east coast. The artists showered the state with an astonishing amount of their paintings, perhaps 200,000 of them. Supply met boom-time demand.

Painting was a means to make money. The speed with which they painted yielded their style; a style that was perfectly suited for the then new “pioneers” who were settling in Florida. The artists – albeit inadvertently – left a legacy about post-war Florida that contributed to shaping the Sunshine State’s image of a tropical paradise.

When, in the mid 1950s, Zanobia Jefferson, an art teacher at the all-Black Lincoln Park Academy, encouraged her student Alfred Hair to take painting lessons from A.E. Backus, the region’s prominent artist, she could have no idea what would follow. Florida’s tropical beauty provided Backus ample inspiration. His time-tested aesthetic yielded Arcadian images. Owning one of his canvases was tantamount to claiming the land. But young Alfred read the images differently; to him they provided a means to escape a bleak future and become wealthy.

Within three years of Saturday morning instruction, Alfred left the artist’s studio and gathered a few of his friends. He offered them an opportunity to rise above social expectations, the remedial inferiority to which “Negroes” were relegated. By teaching them the conventional painting formulas that he had practiced, he gave the others a way out of “Blacktown.”

Alfred reasoned that neither he nor his friends would likely be offered gallery representation, so he created a system to mass-produce their 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.

Alfred knew he would have to paint quickly and a lot if he were to realize his dream of being a millionaire by his thirty-fifth birthday. So he did; he was able to complete a board or two within an hour. Ironically, this fast painting resulted in a fresh variation of his mentor’s traditional art. Alfred’s model became the Highwaymen’s standard. Meanwhile, black self-taught artist Harold Newton sold his landscapes door to door and this gave Alfred the incentive to do the same, but in high gear. Marketing their paintings was as integral as painting. To the Highwaymen, a painting wasn’t considered finished until it was sold.

Newton followed Backus’s model, which satisfied those seeking comfort in the familiar; their seascapes may have been blustery but the waters were navigable. Their formally rendered land exists as if eternal and effortlessly, if not divinely, realized. A viewer could rest assured and behold the wonder of creation, as if overseeing the land on the seventh day. Whereas Hair’s landscapes are in a process of becoming. His windswept scenes conjure the tempest of creation. Hair and the Highwaymen explored a steamy and sultry version of Thomas Cole’s “pathless wilderness.” Their land appealed to those who saw themselves as adventurers in an exotic, untamed place.

Looking at a Highwaymen painting was especially personal; the viewer was the sole arbiter of the domain. Fast painting transformed Florida into a furtive proposition — secret and mystical. It left an impression that compelled viewers to create their own narratives (or fantasies). Sandy shorelines, balmy breezes, and gorgeous sunsets were identifiers of a tropical paradise, and the artists used such iconographic references to ignite viewers’ passions. Whether the sublime presence beckoned one to take a lustful bite of the apple or count one’s blessings at the gates of heaven, the Florida experience was transforming.

The association of Florida as heaven-on-earth has been central to the state’s identity since Spanish colonialism. Imagery this lofty compelled adventurers and artists to romanticize the state. Given its verdant terrain and dynamic weather, the environment was too unbelievable to be literally described effectively, with veracity. Without inspired interpretation the land was pitiably understated. Those familiar with the arts might dismiss Highwaymen paintings, thinking that their in-your-face colors were garish and that the less-than-grand manner treatment was unfinished or simply inferior. For others, Highwaymen landscapes were places of contentment and promise.

The western mountains offered a different experience than could be conjured by the wilds of Florida. Palm trees don’t carry the same metaphoric weight as jagged peaks and fruited plains. But Florida’s primeval topography puts heaven at one’s feet; close to the earth. One could say that a person walks in a state of rapture in Florida. It became perceived as the place to rejuvenate body and soul, a mythic land to experience God’s creation. In a humbler sense, Florida attracted sportsmen (who quickly depleted much of the wildlife) and “invalids” seeking improved health.

Nineteenth century illustrated travelogues lured northerners to the subtropics. The flora and fauna must have appeared as visions from the decks of steamers traveling on the St. Johns River, when the waterways provided the primary means for transportation in Florida. Then came the railroads, which skirted the coasts. Flagler’s and Plant’s grand hotels sprouted at key locales (or, one might say, the hotels prompted the locations becoming prime gathering spots). Advertising tracts continued to draw people to the still-new state.

Pictures proved to be worth the proverbial thousand words, “legitimizing” the descriptive texts that they generally accompanied. Framed hand-tinted photographs showing the virgin territory became souvenirs at the turn of the twentieth century, and they appeared without advertising verbiage. Florida imagery was associated with prosperity from the twenties land boom on, but the signifiers became increasingly pedestrian as middle-class families were able to afford vacations. Visuals were more tantalizing than concrete language for convincing people that they could have better lives in the Sunshine State. Regardless of the subjects represented, the photographs’ soft dreamy hues cast a spell all their own.

Early airbrushed postcards offered a broader array of imagery than had the souvenir photographs. Those pictures were geared for the wealthy, reflecting their social activities amidst the new resorts in the still-wild land. The linen postcards of the forties cataloged the state’s growth, but maintained, of course, a charming presence. Romantic Florida appeared less idealized; the subjects were more ordinary. The wish you were here message that reached the folks back home, via popular 50s-70s glossy postcards, was less a kind sentiment than a tease. Pictures of bathing beauties and oversized thermometers displaying the perfect temperature spoke mockingly of privilege…. Kitsch was knocking at the back door.

Florida’s dependence on tourism and agriculture grew, and image making became fundamental to the industries marketing efforts. Even hurricanes couldn’t dampen people’s spirits. Promoters simply upped the ante, creating an increasingly fantastic place as they vied for tourists and built more hotels. Imagery drove the economy.

Mayor Leonard Haber likely believed his claim that “Miami Beach are the two most recognizable words in the English language.” On the causeway into that island-city, a sign greets visitors with the message “Welcome to America’s Playground.” Jackie Gleason renewed the state’s flagship city’s image by nationally broadcasting from there, claiming it as “the fun and sun capital of the world.” But Tallahassee’s tourism officials epitomized the meaning of the state with the promotional poster featuring a woman’s back: “Florida: The rules are different here.” (The poster was recalled soon after it reached its markets.)

Florida also attracted people in need of jobs and those who preferred not to pay state income taxes or contribute tax dollars to benefit education. The state became “the last resort” for elderly citizens, many of whom lived on fixed-incomes. But it’s mostly remembered as a vacation destination, its beaches providing tourists with a brief escape. A place to fanaticize, if not the Fantasy Island as advertised over the years. Many of the people who moved to Florida, who did not become too disillusioned or who remained there in ecstasy, recognized, in Highwaymen paintings, the vicarious pleasures that brought them to the state. In either case, the imagery improved the prospects for those who called Florida home.

The Highwaymen, like tourism boosters, capitalized on the sensational land. Like early photographs, their paintings gave proof to hardly-believable verbal descriptions, even while the state was yielding to developers’ bulldozers. Perhaps the resurgent interest in the Highwaymen results from the “better times” that the paintings elicit. A vacation remembered. But in spite of any hardships a sojourner might have encountered, including mosquitoes, sunburn, illness and storms, when any angst resided, the memories would become as fond as postcard views. Reality is seldom remembered but dreamed.

Back to Essays

Note that the essays are copyrighted by law. Do not copy whole or in part without written consent, except up to 200 words with citation per fair-usage. Feel welcome to email with comments, questions, and stories about the Highwaymen through the Contact Page.