top of page

Memories of the Highwaymen

I remember when my mother brought home our first Highwaymen painting. Of course, it wasn't termed a Highwaymen painting back then. It was the early seventies and a well mannered, young, black man by the name of James Gibson came into her Coral Gables office selling his Florida landscape paintings. She plucked down $35 for a sofa size painting of a lone palm tree leaning over a narrow river, its reflection glistening in the dark water from the muted moonlight. The coloring wasn't exactly realistic in its bold blues and greens, but it gave her a comfortable feeling of her native back woods Florida. She liked it, it was affordable, and it was big enough to fill the wall behind the sofa!

When I moved to Ft. Pierce a few years later I found a Gibson painting in a thrift store. It looked like the same palm tree, but it was in dark browns and orange tones. I debated paying $15 for the sofa size painting because it wasn't the colors I particularly liked. But, it brought back memories of home, it was affordable, and it was big enough to fill the wall behind my sofa! Living in Ft. Pierce, I frequently encountered these young black artists as they sold their paintings door to door in area offices. Through the years I acquired a collection of the bold and colorful artwork. I bought some at thrift stores, some out of the back of the artist's cars, and some in the office lobbies. I don't believe I ever paid more that $50 for one. Little did I know that these paintings would eventually become coveted collector's items and that zeros would be steadily added to their value! Most of us, by now, know the story of the Highwaymen - a group of 26 black artists who painted their way out of back-breaking, citrus- picking jobs in the late 50's through 80's. Alfred Hair was the undisputed leader of the movement. As a student at Lincoln Park Academy in Ft. Pierce, he showed promise as a painter. His high school teacher arranged for him to study with Bean Backus, an established Florida landscape artist living in Ft. Pierce, who was receiving thousands of dollars for his works. Hair was a quick study and rapidly learned how to use the pallet knife with bold strokes and sweeping motion to create billowy clouds, expansive skies and brilliantly colored landscapes. But while Backus strived for perfection, Hair focused on speed! After all, being black in the 50's didn't give Hair much of a chance of showing his work in art shows or galleries. Instead, he painted in volume. He turned one room of his home into a studio with 2 x 4's covering the walls. Canvas was expensive, so he nailed Upson board (an inexpensive construction material) to the 2x4's and lined them up side by side. He would create a horizon line on ten or twelve paintings at a time, painting the skies, then the clouds, then the landscape in sequence. He was able to turn out a dozen or so in a day. He framed them with inexpensive crown molding (manufactured as door and window trim), and sold them door to door for $20 or $30 a piece. The demand escalated beyond even Hair's ability to speed paint so he enlisted friends to help, He taught them how to frame initially, and then how to sell. Eventually he taught them to paint and his group could churn out up to 40 paintings a day. They took to the highways, stopping at offices, banks and motels along the way, and soon these dreamlike landscapes graced the walls of homes and businesses along the coast. Life was good for the young artists and their dreams were coming true. But, in August of 1970, Alfred Hair was shot and killed in a Ft. Pierce neighborhood juke joint. Some say he was an innocent bystander, others say he was caught in a romantic triangle. Whatever the circumstances, the 29-year old leader of the group was gone. Things changed after Hair's death, though the artists continued to work into the 80's. But, the group was falling apart and some of the artists drifted away. By the 1980's Highwaymen paintings seemed passe' and sales plummeted. Paintings that were once in such demand, were being left at thrift stores, and thrown out with the trash. It wasn't until 1995 that Jim Fitch, art critic and director of the Museum of Florida Art and Culture in Avon Park, coined the name Highwaymen when he was researching Florida artists. He was fascinated by the folk art nature of this unlikely group of artists and began to spread the word. A book by Gary Monroe further popularized the story and a resurgence was born. Highwaymen paintings now hang in New York Galleries and have become highly collectible art. Famous collectors include Hubert Humphrey, Crystal Gayle, Johnnie Cochran, Former Gov. Lawton Chiles and Gov. Jeb Bush. Prices have soared with most paintings now averaging $500 to $5000. Art dealer, Cody McQueen of the Bamboo Beach Gallery in Ft. Pierce; a gallery that deals exclusively in Highwaymen paintings, believes that Highwaymen art will someday sell in the tens and maybe even hundreds of thousands a piece. Terry Green, owner of the Grant Antique Mall, who has been collecting and selling Highwaymen paintings for years, mirrors his opinion.

Yet, you still don't have to be a Rockefeller to acquire one of these treasures! The sheer abundance of Highwaymen paintings, estimated to be in the 200,000's, keeps them relatively affordable. Many of the original Highwaymen have come out of retirement and are actively painting again. There's even a new generation of Highwaymen offspring aspiring to carry on the tradition. Granted, the unavailability of Upson board and the spontaneity and speed of the early movement makes the vintage paintings more valuable; but most are still within the grasp of the average person. Stories like mine are abundant on the Treasure Coast, as we live in the birthplace of the Highwaymen. To me, the story of the movement and the memories of the young black men who rose beyond the bonds of segregation and brought art to the masses are far more valuable than the monetary return on my minimal investment. How wonderful to have lived among these passionate, freethinkers and watch them finally soar into national fame.


bottom of page