Film producer telling story of Highwaymen artists

Todd Thompson is in the process of casting for the film that recognizes the black Florida artists of the 1950s and ’60s who sold their paintings on the side of the road.

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“We live in a world where black is black and white is white,” says the voice in the film clip. “Who would have thought all the colors in between would change our lives forever. In time they would call us artists, but to most, we was known as The Highwaymen.”

These landscape artists shared their low-paying and underappreciated talents starting in the 1950s — and only since the 1990s has their art been appropriately recognized.

Todd Thompson, a writer, producer and director who lives in the Dr. Phillips area, has been working on a project that is two decades in the making, he said.

His Stars North Films is in the process of casting for “The Highwaymen,” a film based on the true story of the artists who sold their colorful and tranquil paintings along the coastal roads of Florida. The movie features an eccentric art collector looking for the artist behind a mysterious, unsigned painting and discovering the last great art movement of the 20th century, Thompson said.

The project has two parts, he said — a feature-length film and a six-part documentary series.

 “We’ll be capturing and telling the Highwaymen story two different ways,” Thompson said. “Some people prefer documentaries, some prefer film — so we’re going to reach a wider audience.”

He said his fascination with the artists started years ago when a coworker suggested he look into the story of The Highwaymen. He did some research and was immediately hooked, he said.

“I knew that it would be a story I would one day tell,” he said.

He has been writing the film’s script ever since.

“I have been living and breathing this project for 20 years,” Thompson said. “The first one I met was James Gibson. …  Through the years I met Al Black, Maryann Carroll, Carnell “Pete” Smith. … I’ve met most of them over the years.”

Each one of them could have their own film, he said. In the documentary series, viewers will see in-depth discussions with these artists.

“It was apparent when I first sat down to do this that there was a lot of colorful information, historical and engaging,” Thompson said. “The film will be fun. The documentary will be a deep dive. … It’s really going to take on an interesting perspective from the collector’s point of view.”

Seeking and buying Highwaymen paintings has turned into an obsession for some collectors, he said. He owns a few painted by Black.

The documentary and the movie are being filmed simultaneously. Thompson is producing and directing the feature film; he is producing the documentary, which is being directed by Joy Kigin.

“It’s such a fascinating story,” Thompson said. “Sometimes when you’re talking about a painting, you’re talking about someone who’s been dead for years. (The Highwaymen) are watching their work go up in value.”

Todd Thompson is producing a documentary and a film based on the story of The Highwaymen artists.
Todd Thompson is producing a documentary and a film based on the story of The Highwaymen artists.

Filming was halted briefly because of COVID-19, but Thompson said cameras will start rolling soon on the documentary. He expects to start shooting the feature film by mid-July. The entire project, which will include two hours of content for the film and about six hours for the documentary series, could take up to 18 months to complete.

Thompson is hoping the project will act as a segue to incorporating the artists’ works into the curriculum of local schools.

“It’s an extremely important story,” Thompson said. “And aside from what’s been going on in the United States … it’s a very timeless tale of the human spirit and the American dream. … I think what I relate to so much is the fact that these guys in one moment were able to survive and thrive in a lot of ways at a time when they weren’t allowed to walk in certain rooms or be around white people.

“Their devotion and passion for everything just resonated with me, and I want that to be what you get out of the film — a sense of inspiration,” he said.

To watch a video clip of “The Highwaymen,” visit

Writer, director and producer Todd Thompson befriended Mary Ann Carroll, the only female Highwaymen artist, before her death in 2019.
Writer, director and producer Todd Thompson befriended Mary Ann Carroll, the only female Highwaymen artist, before her death in 2019.




Amy Quesinberry

Community Editor Amy Quesinberry was born at the old West Orange Memorial Hospital and raised in Winter Garden. Aside from earning her journalism degree from the University of Georgia, she hasn’t strayed too far from her hometown and her three-mile bubble. She grew up reading The Winter Garden Times and knew in the eighth grade she wanted to write for her community newspaper. She has been part of the writing and editing team since 1990.

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