THE DRAMATIC TRUE STORY of the Highwaymen, the Florida artists who made a living selling paintings from the trunks of their cars during segregation, is being made into a feature film.

“The Highwaymen” is about a group of 26 African American artists, most of them self-taught, who turned out countless paintings of Florida’s lush, natural landscapes. Rather than endure backbreaking work in local citrus groves, they leveraged their artistic talent and sales acumen.


ALFRED HAIR, “Untitled (Beach Scene with Palms),” n.d. (oil on board, 24 x 36 inches). | © 2017 Doretha Hair Truesdell, Courtesy the Lightle Collection. Photo by Tariq Gibran


Only 19 when they got started in the late 1950s, Alfred Hair led the group. Shut out of galleries and museums, Hair developed a creative sales strategy—traveling up and down the highways and roadways of Central Florida’s Atlantic coast, offloading the paintings for about $25 each. Their customers were mostly white tourists and businesses owners at doctor’s offices, law firms, beauty salons, and hotels.

On May 27, Variety reported a longstanding film project about the artists is moving forward with pre-production. “The Highwaymen” is based on a script by Lucien Christian Adderley and Richard ‘Byrd’ Wilson, black writers with a track record telling meaningful, Florida-based African American stories. Adderley and Wilson are in their second season of writing “David Makes Man,” the OWN drama created by Tarell Alvin McCraney, who shared the adapted screenplay Oscar with Barry Jenkins for “Moonlight.”

“The Highwaymen” is based on a script by Lucien Christian Adderley and Richard ‘Byrd’ Wilson, black writers with a track record telling meaningful, Florida-based African American stories.

Todd Thompson is set to direct “The Highwaymen” and casting is underway. (The commencement of filming depend upon state and industry guidelines regarding health and safety surrounding COVID-19.) The project is being produced by Stars North Films, Thompson’s production company, with Tim Franta, Kathryn Kelly and Joy Kigin. The film has been in the works for nearly a decade. In 2012, the Orlando, Fla.-based Stars North tried unsuccessfully to raise $100,000 on Kickstarter for “The Highwaymen.”

(A Netflix film by the same name about two former Texas Rangers on the hunt for Bonnie and Clyde, stars Kevin Costner and Woody Harrelson.)

Given the sales method of the entrepreneurial artists, a white gallery owner coined the Highwaymen moniker in the early 1990s. The nearly all-male group included one woman. A few of the artists are still living and continue to paint. They are celebrated by collectors and the community at-large and their paintings, particularly the early works, is in high demand.

In a statement, Adderley and Wilson said: “We’re excited to be part of this project because of our desire to tell Florida stories and take responsibility for getting them out there on a level that exposes the world to Black history in our home state. We see similarities between the Highwaymen and ourselves as a team of artists who once traveled from town to town sharing our poetry.” CT


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Early trailer for “The Highwaymen,” which has been in the works for nearly a decade and is finally moving forward with pre-production. | Stars North Films


An exhibition catalog was produced to accompany “Living Color: The Art of the Highwayman” and includes an essay by Gary Monroe, who guest curated the show. Monroe has authored several other books about the Florida Highwaymen, including “The Highwaymen: Florida’s African-American Landscape Painters” and volumes about key individual figures in the group—“Mary Ann Carroll: First Lady of the Highwaymen,” “Harold Newton: The Original Highwayman,” and “The Highwaymen Murals: Al Black’s Concrete Dreams.” Another publication, “Alfred Hair: Heart of the Highwaymen” is forthcoming in September. In addition, “Florida’s Highwaymen: Legendary Landscapes” by Bob Beattyl provides an overview of the Highwaymen.


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