[Essay] The Art of the Highwaymen: From the Woodsby Family Collection

The Florida Highwaymen occupy an unusual and fascinating space in the history of art. When one mentions “the art of the Highwaymen” to many Floridians, their ears perk up and their eyes brighten, with a glowing and knowing fondness for homegrown art. When you mention “the art of the Highwaymen” to non-Floridians, most look at you with little or no recognition of what you are talking about.

What accounts for this discrepancy? Why have the Highwaymen — along with their stories and their paintings  — garnered widespread fame and renown in Florida but not in the larger canon of popular art history? This original exhibition, showcasing nearly 70 works drawn entirely from the private collection of the Woodsby family (and never before shown in the space of a museum) aims to explore the complex phenomenon of the Highwaymen and to situate them rightfully as pioneers of modern art.

Indeed, starting in the 1950s, a period when America was still in the throes of segregation, the Highwaymen defied all odds. A prodigious group of African-American artists who plied their trade painting Florida’s landscapes and sold their work from the trunks of their cars, the Highwaymen discovered success in simplicity. With landscapes that read now like a land remembered, laced with nostalgia, the Highwaymen found a niche to call their own, producing an estimated 200,000 works that have become beloved features of local homes, hotels, restaurants, and museum collections today.

The Woodsby Family Collection &  “Johnnie’s Hideaway”

Ron Woodsby began collecting Highwaymen landscapes with a very specific purpose in mind:  as he envisioned the atmosphere for his family’s now-iconic Johnnie’s Hideaway restaurant in Orlando, he sought to evoke vintage Florida, all the way from the light fixtures to the paintings on the walls. How better to create the aura — and picture — of a beloved Florida of the not-too-distant past than by decorating the restaurant with the mid-century art of the Highwaymen? As Ron explains, “I was looking for something other than fish but Floridian.” What started as a business-minded venture nearly 20 years ago — when Ron began searching for Highwaymen work at auctions — turned quickly into a family passion, however. Since then, members of the Woodsby family have become veritable experts in the history and lore of the Highwaymen, and their collection has grown to nearly 270 paintings. 

Important to the Woodsbys’ collection is the uniqueness of the paintings they have purchased. While many collectors seek Highwaymen landscapes that read timelessly as landscapes alone — without figures, wildlife, boats, or houses that might date the works to a specific era — and with signature features like “fast grass” (quickly painted grass in the paintings’ foregrounds), the Woodsbys have alternately preferred paintings that are grounded in and indicative of the period in which they were produced. Thus, while all of the works in the collection still contain the staple aspects of Highwaymen landscapes, the Woodsbys’ collecting focus turned toward works with those more rare, lesser-seen features, like dirt roads, laundry lines, or even an alligator. Moreover, the family has sought examples that are made clearly by the hand of a singular artist with individual talents, despite the shared general subject matter and overall manner of the Highwaymen group as a whole. As the collection grew, Ron explains, “The goal was unusual Highwaymen paintings with unique qualities to each artist, not the universal roadside collectible aspects. We wanted to find Highwaymen works that typified the best work of each artist and with recognizable aspects of the past Florida landscape, a time that was captured by them that doesn’t exist anymore.” 

The Origins of the Highwaymen:  Harold Newton and Alfred Hair 

No history of the Highwaymen can begin without acknowledging the key influence of Fort Pierce artist and teacher A.E. “Beanie” Backus (1906-90). In the years immediately following the Second World War, Backus’ Old Studio was a font for artistic conversation and education, as much as it was a commercial gallery, and his success producing and selling scenes of Florida’s iconic landscapes propelled other artists to follow closely in his footsteps. While Backus himself and the majority of his clientele were white, young Black artists like Harold Newton and Alfred Hair discovered in Backus a welcoming mentor in whose paintings they could find inspiration, a style they could emulate, and a marketability upon which they could expand.  

With Backus’ guidance and manner of painting providing a jumping-off point, Newton (1934-94) and Hair (1941-70) were among the first artists to mimic his style and subject manner, albeit often with swifter manufacture and cheaper materials (such as Upson boards). That they were African-African artists working toward careers as painters in the South adds to the enormity of their enterprise — however historically overlooked. Considered widely as the founding members of the group that has come to be known as the Florida Highwaymen, Newton and Hair tapped into a clever twist on Backus’ landscapes:  they would create and sell their landscapes far from the traditional studio and gallery settings, setting the stage for fellow mid-century Black artists to find receptive audiences for their works up and down Florida’s major and minor roadways, at souvenir stands, and door to door. 

Defining an Aesthetic:  The Style(s) of the Highwaymen

What makes a Highwaymen painting a Highwaymen painting? While we can locate individual traits importantly among the work of each Highwaymen artist, the group’s landscapes share some overarching aesthetic, thematic, and material characteristics. If you look at the paintings on display in this exhibition, you will immediately note some recurring aesthetic elements:  “fire skies” (brilliant renditions of the sunset in dynamic reds, yellows, and oranges), “fast grass” (painted rapidly with a palette knife), and “hallelujah clouds” (so emblematic of Florida’s landscapes). Thematically, too, the Highwaymen’s landscapes focus on Florida’s natural beauty, its beaches, marshes, palm trees, and native flora and fauna. This subject matter spoke broadly — and appealingly — to tourists and native Floridians alike.

Harder to notice at a glance but no less essential to our understanding of the Highwayman, affordable materials were a necessity; painting out-of-doors on construction materials such as Upson boards — along with more traditional materials like paint brushes, palette knives, and oil paints — allowed the artists to maximize their products and their profits. Interestingly, because it takes paint longer to dry on the hard surface of an Upson board, as opposed to, say, on a canvas, Highwaymen paintings were often still wet while being sold. As a result, you may notice remnants of paint removed unintentionally from the edges of some of the works in this show, rubbed off when framed soon after completion (frequently in crown-molding, another inexpensive and accessible material).

“High” Art vs. “Low” Art:  More Than Souvenirs

While it may be tempting, given their history, to write off the Highwaymen’s paintings as inexpensive “roadside” trinkets or to study them principally for their nostalgia-driven aesthetic appeal, it is important also to re-examine the Highwaymen beyond the confines of Florida lore to note how they fit both within and without the history of art as it has been written. The Highwaymen do not appear as standards of art history textbooks; one will be hard-pressed to find any mention of their contributions, but their backstory and artistic production fall into a long art historical lineage of landscape painting, popular, affordable, accessible art, and art-business savvy.  

At the same time, we must ask ourselves:  why have we not cemented in that history the remarkable achievements of African-American artists who created a whole art movement of their own? To be certain, being a Black artist at any time, let alone in the middle of a still-segregated 20th-century America, offered little hope for respect or success. The art world has not been a welcoming place for minority artists, but, despite all, the Highwayman discovered a niche area of consumer interest, as artists have done over the ages. Painting en plein air (out-of-doors) is long associated with Western art history, particularly the 19th century scenes that put the enormously celebrated French and American Impressionists and Hudson River Landscape painters on the map — and in the world’s collective imagination as exemplars of “high art.” In contrast, the Highwaymen’s explorations of Florida’s idyllic ecosystems are far less widely known or universally praised, a consequence perhaps of their roadside manufacture and sale (equating them with “low art”), their being produced far outside the centers of the art world (in the Jim Crow-era South, rather than in Paris and New York), or because of the backgrounds of the artists themselves.

The Highwaymen in 2022

The story of the Highwaymen is a story grounded deeply in its era, but how we look at that story can transform in eye-opening ways when revisited through the lens of the 21st century. From their landscapes themselves — which read now as snapshots of a more pure Florida past, memorials to sites and ecosystems mostly unmarred by human touch and construction — to their overcoming limitations of race, the Highwaymen can be seen anew in the broader context of art, political, and social history.  In fact, it may be the multi-layered nature of any conversation about or re-consideration of the Highwaymen that accounts for the group’s lasting and widespread appeal.  

Each new generation that discovers the Highwaymen, whether in a grandparent’s art collection or in an academic museum exhibition like this, finds something in the backstory — resilience, challenging perceptions of race, self-taught artistry — or in the landscapes themselves — familiar Florida terrain or postcard-like remembrances of youthful road-trips — that resonates with their own lives. To be certain, the Highwaymen continue to fascinate for their unique and under-appreciated place in the history of art as much as for their eliciting a sense of shared, almost kinship-like pride in visitors and collectors for their unapologetically and authentically Floridian art. 

By by H. Alexander Rich, Ph.D., Executive Director and Chief Curator

Rodin: Contemplation and Dreams will be on view February 12 through May 22, 2022 in The Dorothy Jenkins Gallery and Gallery II.