The Florida Highwaymen and the Art of Black Free Enterprise
The fascinating story of the black painters who painted vivid Florida landscapes and defied Jim Crow segregation.
An artistic career is rarely viewed as a viable path to social and economic mobility. But art offered a meaningful path to freedom for a group known as the “Florida Highwaymen,” a collective of black painters during Jim Crow segregation who made a living selling landscape paintings.
From the mid‐1950s to 1970, this enterprising group of black men and one woman created a portfolio of approximately 200,000 paintings. Mostly self‐taught painters who mentored and supported one another, they were often excluded from the whites‐only world of art galleries and public events.
The brushstrokes of a typical Highwaymen painting featured vivid scenes of Florida’s vibrant ecological landscape, replete with swaying palm trees, breathtaking sunsets, rich blue oceans, and vibrant red poinciana trees. They painted on cheap upson boards–which were more often used in home construction–and framed them with crown molding brushed with gold or silver paint to give them an antique finish. 1
The paintings were popular with owners of banks, motels, and laundromats looking for inexpensive art to decorate their businesses in a style that evoked life in Florida. For those traveling within the “Sunshine State” of Florida, these paintings became prized vacation souvenirs due to their affordability and the ease of transport. The Highwaymen themselves even used their work to barter for things like gas for their automobiles.
Despite the popularity of their paintings, the Highwaymen faced many barriers in Florida during the fifties, a time of racial segregation, social unrest, and often violence. The White owners who dominated the art gallery world typically ignored or purposefully excluded works by black artists. Nevertheless, the Highwaymen persevered by selling their works from their car trunks in cities like Fort Pierce and Vero Beach as well as along U.S. Route 1 off Florida’s Atlantic coast.
The Florida Highwaymen began with a man named A.E. “Beanie” Backus in 1906, a local self‐taught artist who developed beautiful artistic scenes with a palette knife. Viewed as the catalyst for Fort Pierce’s artistic scene, Backus created an open door setting for his atelier which attracted many visitors. 2
In 1954, Backus took on a man by the name of Alfred Hair as his studio assistant. Benefiting from the mentorship of Backus, Hair, along with a man named Harold Newton, helped fuel the Highwaymen artist movement. Hair rapidly built a name for himself through his artwork, driving up and down the beachfront roads of Fort Pierce with music from the legendary singer James Brown emanating from his car. 3
By the late 1950s, Hair had built a group of 26 black landscape artists in Florida. While initially taught by Backus, they evolved into a vibrant, tight‐knit community of painters who mentored and learned techniques from each other while developing their own unique styles.
Traversing the highways and thoroughfares of Central Florida’s Atlantic coast, they sold paintings for between $25.00 and $35.00 each, typically on the same day they were created. They were transported by automobile or bike in custom handmade frames, often still wet with oil paint.
The Highwaymen’s entrepreneurial success came as most blacks were limited to work in Florida’s factories, tomato fields, and citrus groves. The Highwaymen used their artistic adroitness to earn a living that wasn’t dependent on low‐wage, blue‐collar labor. These earnings provided the group and their families with an independent lifestyle beyond what they had ever thought possible.
For some, it even yielded the opportunity to purchase the ultimate status symbol: a new car. Few possessions held as much symbolism for Americans–both black and white–as the automobile, which meant the ability to easily travel, commute, and move, all actions that undermined the physical boundaries of segregation.
However, in 1970 the group lost its prodigious leader when Hair at 29 was killed in a barroom brawl. Combined with shifting public tastes and new competition from mass‐produced paintings, the Florida Highwaymen entered a period of decline.
In an article entitled “Memory, Myth, and Legend: Missing Brushstrokes,” Alfred Hare’s wife Dorothy Hair Trusdell and Highwayman Al Black offer some insights into some of the hidden dangers that Hair and the group faced as their art grew in popularity.
“Back then, we were the talk of the town, because we had more money than the average man walking around. That meant new cars, clothes, and weekends at the dog track. But with that success came attention. And the attention would prove deadly. Alfred’s success made him a target for jealousy. It looked like everything he touched turned to gold.”
It is rumored that an agricultural worker named J. L. Funderburk, who had been at the bar the evening Hair was killed, had accused him of flirting with a woman he liked. Black says that he remembers Funderburk telling the barroom, “I’ll kill every one of you painters,” before stepping outside to get the gun he used to shoot Hair.4
Despite the chilling effect that this unfortunate incident had on the collective, the legacy of the Florida Highwaymen still resonates to this day, reflected in their unique painting style and their determined effort to create economic independence and freedom during segregation. Today, their work is among the holdings of the Smithsonian Collection and the Highwaymen have been inducted into the Florida Artists Hall of Fame.
Even so, few non‐experts outside of Florida have heard of the Florida Highwaymen and their achievements. Yet, amid the backdrop of Jim Crow and racial discrimination, their work serves as a profoundly important reminder of the power of free enterprise, mutual aid, and self‐reliance.