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Alfred Hair painting on upsom board

The Early Years (1950s to 1970s)

The early years of the Highwaymen story are varied and complex. When the artists became known as “The Highwaymen” in the mid-1990s, they were depicted as a relatively cohesive group of 26 individuals (25 men and one woman), and their history has been told as one basic story. But no one story accurately characterizes the early years of this group of ambitious artists, and in order to understand the Highwaymen well, some knowledge about the time and place in which they were educated, painted, and sold their work is needed. Much of what follows may blur fact and legend, as the story continues to be told and retold. As with most legends, some lies, or exaggerations, tend to creep in.

In the 1950s, Fort Pierce was a segregated town, like most places in the southern United States. World War II was over and everyone, black and white, wanted a part of the American Dream. According to historian, Gary Mormino, Florida’s greatest export at the time was that it was a place where optimism prevailed. The Sunshine State was a land of perpetual hope, and the black youth of Fort Pierce felt it as strongly as anyone else. Many of their parents had migrated from other states, knowing that Fort Pierce had jobs for farmworkers. As so many of the future Highwaymen knew, it was a time when work could be found if you wanted it. Students and young adults, male and female, would often hop a bus to pick fruits and vegetables to earn money. But working the fields was hard labor and, like anyone else, the young adults who became the Highwaymen were looking for better opportunities.

The segregated African American area of Fort Pierce centered around Avenue D, a thriving commercial district where blacks owned businesses and everyone took care of each other. Residents had small gardens and they could always fish or hunt for food. Although times could be tough, a living could be eked out of the land, the neighborhood, the coastal waterfront and the surrounding agricultural businesses.

155944955Most people say the Highwaymen’s landscape painting started with Alfred Hair who, in the late 1950s and early 60s took art classes from A. E. “Beanie” Backus, a white landscape painter who welcomed students and visitors of any color to his studio. Hair was good looking and friendly; he had a charismatic personality and an entrepreneurial spirit. He saw that Backus was earning a good living from his Florida landscape paintings, and he also knew that a black man in the segregated South had little chance of following in Bean’s footsteps—at least not with gallery representation and artworks with hefty prices. So he took another route: he decided to make a lot of paintings by creating them quickly and selling them inexpensively on the road.

BEANIE BACKUSNot only did Hair learn to paint fast, he also painted in assembly-line fashion. When asked how many paintings Hair painted, Backus said that he claimed to paint 30 in an eight hour day but, he said, “there’s no way to prove it.” Hair taught others to make frames for him and, eventually to paint in the backgrounds so he could move even more quickly through his work. Other young artists did the same, sometimes signing someone else’s name to their work when they thought that paintings with their name were flooding the market.

The young Highwaymen began using house paint and then quickly moved to oils. They conserved on paint and brushstrokes. Cheap materials were selected for a painting surface, Upson Board (a builder’s sheeting product used as wallboard and in eves) and later Masonite. Sheets were cut so that nothing was wasted. Typically board sizes were 2 x 3 feet, 18 x 24 inches, and 12 x 24 inches. They used shellac as a primer. Crown molding (at 9 cents a foot), and sometimes the wood from orange crates, was used for frames. Standard sizes meant that they could be easily stacked in cars and vans. Paintings generally sold for $25 to $35, depending on size.

Hair’s goal was to be a millionaire by the time he was 35. He may not have reached that goal, but in the late 1960s, he and the other young, ambitious artists and salespeople were bringing in wads of money. They owned fancy cars, dressed well, and traveled.

Harold1But Hair wasn’t the first young black man in or around Fort Pierce to start painting. Harold Newton, who was older than Hair, met Beanie Backus in 1954. Newton had been painting religious scenes and selling them door-to-door before Hair began taking his paintings on the road. Backus encouraged Newton to change his subject matter to landscapes and the young artist complied.

Livingston Roberts was also painting before he met Hair. It was a perfect convergence of people and circumstances. These young African American artists taught and learned from Beanie Backus, each other, and instructed themselves through trial and error. They often pooled their paintings for selling on the road.

Still, not everyone who would become a Highwayman was centered in the Fort Pierce area. Robert Butler (b. 1943), a young painter from Okeechobee, didn’t work with the Fort Pierce artists, but he too was painting the Florida landscapes. He learned about the other black artists by being on the road. Other artists would center in Gifford or Vero Beach, although the synergy for the effort was and remains Fort Pierce.

Not all the artists were interested in painting quickly like Alfred Hair and the group that painted at his house on Dunbar Street. Some artists, such as Charles Walker, were more interested in detail and some, like Mary Ann Carroll, preferred to paint alone. Many never participated in the group assembly line Hair devised. But James Gibson and others liked to paint several similar paintings at one time and painting fast and selling fast was the goal. Many of the artists painted outside, where they had room to spread out their work, and the sun could dry the oils—although Florida’s humidity kept them wet and tacky to the touch. Consequently, painted fingerprints can often be found on the frames and backs of early Highwaymen paintings.

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While it might seem strange to some that so many young black men took up painting in the 1950s and 60s, in some ways the times encouraged it. Paint-by-Number kits were developed and marketed in 1950, and they could be found everywhere. People all over the country, regardless of class, race, or gender, used them and hobby art was everywhere. Additionally, Grandma Moses (1860-1961) made it possible for all kinds of people to believe that they could become artists. While the young Highwaymen may not have been conscious of the democratization of painting, it certainly helped their customers think more openly about purchasing paintings by unknowns.

Regardless of the hobbyist mindset of the times, the young artists’ success was astonishing. By the end of the 1960s, tens of thousands of paintings had been made and sold. Oil paintings were loaded into cars still wet and often sold that way. At the time, there was no 1-95 or 1-75, so the artists and salesmen moved steadily up and down the east coast of Florida and throughout the interior of the state.

As salesmen, they were smart. They tried to avoid public eye because soliciting was unwelcome in many places, and blacks moving about in white spaces during Jim Crow times could be dangerous. But they found enthusiastic buyers who had a little money to spend for a painting that could decorate an office, a restaurant, or a hotel lobby. The Highwaymen had found their market and they were savvy about how they went about developing it.

In many ways, the good life ended on August 9, 1970, when Alfred Hair was shot during an altercation in Eddie’s Place on Avenue D. It was a senseless shooting that catapulted many of the artists into despair. Some kept on painting, but others stopped, feeling the loss of the magnetic man they considered their leader. About the same time, many of the artists were landing in jail for soliciting without a license and it was getting costly and time consuming for someone to bail them out. Additionally, the market had been flooded with Highwaymen paintings and they were ending up in flea markets and garage sales. Their paintings’ early marketability had waned, at least for a time.