A salty breeze ripples through sawgrass; pastel skies stretch over a marsh and its shoreline. It’s a quintessential Old Florida scene. But in the new film Legends of the Highway, it’s the very canvas on which a quiet art revolution played out right here in South Florida.
The film tells the powerful story of the Florida Highwaymen. Beginning in the 1950s, this collective of self-taught Black artists painted local landscapes and forged their own path in a segregated world. The movie follows eight of the original 26 Highwaymen. Among them: Alfred Hair and Harold Newton (two of the movement’s visionaries) as well as Mary Ann Carroll (the only woman in the group), and A.E. “Beanie” Backus (a white landscape painter from Fort Pierce who, despite the era’s racial barriers, helped guide both Hair and Newton).
Often working on inexpensive upson board or Masonite instead of more costly canvas, the Highwaymen painted dozens of scenes each day using fast, expressive brushwork. Their imagery—palm trees against blazing sunsets, calm marshes under moonlight, rivers reflecting golden skies—became emblems of both the natural beauty of Florida and the bold entrepreneurial spirit of the artists who painted them. Denied access to segregated art galleries, they turned to the open road to sell their paintings for about $25 apiece. Today, their highly collectible works are frequently sold at auction for several thousand dollars each.
Actor Kelvin Hair II plays his grandfather, Alfred Hair. “It was a dream come true to tell his story and the story of his group. They overcame so much to make their art,” Hair II says. “Even as an artist today you want your art to be seen. Their story gives me the drive to keep going.”
For director and screenwriter Marquand Ragland, the notion of the Highwaymen being self-taught artists resonated deeply. “I wanted people to see that even though these people were self-taught, and they built a legacy that is so powerful. As a self-taught filmmaker, their story is extra meaningful
to me.”
Through Ragland’s lens, the film reveals how adversity shaped the Highwaymen’s resolve as artists operating in Jim Crow–era Florida. Galleries and institutions shut them out. The open road could be dangerous. Yet, they found a way not only to survive but to thrive, building a business, a community, and a lasting cultural legacy. Now, 70 years later, their story is available to view on a variety of streaming services (at press time, available on Amazon Prime Video and Fandango at Home), plus DVD.
“These artists painted their way to freedom,” Ragland says. “I’m proud to share their stories and celebrate their successes with a wider audience.”
Museum Moments
See the Highwaymen’s paintings firsthand at one of two museums in Fort Pierce:
A.E. Backus Museum and Gallery
Once known as the Fort Pierce Art Gallery, today’s A.E. Backus Museum & Gallery was modeled after the artist’s Old Studio on the north bank of Moore’s Creek. The museum contains the largest public collection of paintings by Backus, and is dedicated to presenting and collecting his works and works by the original Florida Highwaymen.
Renovations are nearing completion on the historic building that will house a new Florida Highwaymen Museum. Slated to open this year, the museum plans to house one original work from each of the 26 first-generation Highwaymen.
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