Being an artist is rarely seen as a ticket to prosperity and social mobility. But for Florida’s historical “Highwaymen”—a group of around two dozen black painters who made a living selling their landscape paintings out of car trunks in the Jim Crow South—art was something of a pathway to freedom.
From the 1950s through the ’70s, the Highwaymen produced over 200,000 paintings of Florida’s diverse ecology—vivid scenes depicting fiery red sunsets over aquamarine bays or the scraggy, Spanish moss-covered banyan trees stretching over the state’s backwater regions. Hawking their work straight from their car trunks, the group sold paintings to day-tripping tourists along U.S. Route 1 on Florida’s Atlantic Coast and to (predominantly white) business owners in the banks, motels, and laundromats of their native Fort Pierce, even as galleries turned them away.
The paintings originally went for $25 or $30 each, and were typically sold on the same day they were made, transported in bundles by car or bike in handmade frames and often still glistening with wet oil paint. Today, paintings by the Highwaymen are included in the Smithsonian Collection; they can clear $10,000 at auction or in private sales; and originals by the group’s most prominent figures, Al Black, Alfred Hair, and Harold Newton—who is estimated to have made over 30,000 paintings alone—are coveted by a diverse fan base that includes the Obamas and Steven Spielberg.
This little-known history begins with a man named A.E. “Beanie” Backus, the godfather of the Highwaymen. Backus was born into the racially segregated city of Fort Pierce in 1906, when the town’s black and white neighborhoods were divided along train tracks. A largely self-taught artist, Backus created dramatic landscapes with a palette knife, combining what he’d learned at summer art classes at Parsons in New York City with his encyclopedic knowledge of Florida’s wildlife and his love of its epic thunderstorms. Considered the catalyst of Fort Pierce’s landscape movement, Backus kept his studio open to all, and took on a local student, Alfred Hair, as a studio assistant in 1954.
Hair soon graduated from making frames to learning the tools of the trade and developed his own approach to Florida landscape painting: quickly rendered and dramatically lit scenes with infinite skies. Hair made a name for himself painting dozens of artworks a day and driving the beachfront strip of Fort Pierce in search of customers, while blasting music by James Brown. (He worked at that pace up until his tragic death by gunfire at age 29, in 1970.)
The seeds of the Highwaymen had been sewn, with many more schoolboys and girls making the pilgrimage to Backus’s studio to develop their own artistic careers. Author Gary Monroe, who has written about the Highwaymen, describes a key group of nine painters emerging from a generous headcount of 26 loose “members.” Those central figures included Harold Newton, James Gibson, Livingston Roberts, Roy McLendon, and Mary Ann Carroll—each with their own unique artistic style and business approach.
The group functioned something like a social club. They’d get together at the local dog track with the money they made each day for an evening of hard-earned recreation and story-swapping. But contrary to popular belief, the artists were fiercely independent during business hours. Save for Harold Newton and Livingston Roberts, who could often be seen painting together along U.S. 1, each Highwayman stuck to his or her own part of the Fort Pierce, Clifford, and Vero Beach areas.
With persistence, charm, and boundless entrepreneurialism, this band of outsiders tapped into the growing art market of post-war America, overcoming the cultural barriers facing minorities within the Jim Crow-era South. “People would look beyond the race politics of the South when buying my father’s paintings,” explains Kay McLendon, who is currently helping her father Roy prepare for an upcoming exhibition “Blazing the Trail: Vintage Paintings by the Original Highwaymen” at the A.E. Backus Museum in Fort Pierce. “They’d sometimes ask him to leave the painting and come back in two weeks, but they would always pay him. There was trust there; the art really bonded people.”
Like many other Highwaymen, McLendon had a large family to take care of—including 8 children—and he used his passion for painting as a means to sustain them. Back then, $25 or $30 was more than he earned in a week as a construction worker. Selling a handful of paintings each week enabled the men and their families to enjoy a more prosperous lifestyle than they ever thought possible. Some even achieved the ultimate status symbol: a car. “One time, Roy came back home in a pink Cadillac; my mom told him to take it right back,” laughs Kay McLendon. “But you know, he was making good money if he was able to come home in a pink Cadillac.”
Nowadays, the legacy of the Highwaymen is kept alive by a slew of collectors, curators, writers, and historians, who continue to be captivated by their story. “From the highway to the national museum, the story of the Highwaymen is an essentially untold piece of the American Dream,” says collector-curator Roger Lightle, who owns over 400 original Highwaymen artworks and continues to curate, lecture, and exhibit their work internationally. “These Florida backwater scenes are a reflection of the artists themselves. They are their paintings.”