Curator Jim Fitch’s Tips to Identifying an Authentic Highwaymen Painting

There are only 26 original Florida Highwaymen artists. They are:
Curtis Arnett
Hezekiah Baker
Al “Blood” Black
Ellis and George Buckner (brothers)
Robert Butler
Mary Ann Carroll
Johnny and Willie Daniels (brothers)
Rodney Demps
James Gibson
Alfred Hair
Issac Knight
Robert L. Lewis Jr.
John Maynor
Roy McLendon
Alfonso “Pancho” Moran
Sam, Lemuel and Harold Newton (brothers)
Willie Reagan
Livingston “Castro” Roberts
Carnell “Pete” Smith
Charles Walker
Sylvester Wells
Charles “Chico” Wheeler.

Generally, the earliest and most collectible work is on Upson board and was created between 1955 and 1987. After 1987, Upson board was no longer manufactured and the artists switched to Masonite or stretched canvas. This provides a reliable way to date their work. The value of Highwaymen paintings varies greatly depending on date of creation, size, condition, artist, color scheme and subject matter, but the paintings have fetched as much as $25,000.
It took a 1995 article in Antiques & Art Around Florida by writer Jim Fitch, a curator and art-acquisition agent for the investment partnership Florida Masters Collection Ltd., to change the tide. In the piece, Fitch chronicled a group of unknown artists on the eastern coast of Florida, describing how, 40 years prior, the group had traveled the highways “peddling” its paintings from the backs of their cars. He called his discovery “The Highwaymen.”

Where Fitch left off, Geoff Cook picked up. In March 1998, Cook, an Orlando, Fla., nursery grower with a passion for landscapes, spied an image of a vibrant Johnny Daniels (1954-2009) painting of a sunset in the Orlando Sentinel’s Florida Magazine. In true “Highwaymen” fashion, Cook took to the road, heading east. He scoured antique shops, thrift stores and auctions along the coast, acquiring his first painting by Harold Newton (1934-1994) for $85.

He’d repeat this pattern for 10 years. Voraciously collecting and gathering information about the artists and consulting with dealers, collectors and the artists themselves, he ultimately became the expert on all things Highwaymen and, in 2008, produced a PBS documentary on the subject. He generously lends his art to museum exhibitions, and his once-massive collection (at one time it exceeded 3,500 paintings) today has settled at a more modest number of 250 pieces valued at $1.5 million.

Cook routinely fields offers for paintings in his collection but sells judiciously. In ­August of this year, he sold a 1958 Harold Newton painting for $25,000 but declined an offer of $50,000 for another Newton painting, “1961 Self portrait,” because the “absent landscape is a rare subject matter, making it an unusual painting.”

The 18 surviving Highwaymen are now in their 60s and 70s, and all except one still actively paint. In 2000, 26 artists were identified as Highwaymen, and their legacy was cemented four years later when they were inducted into the Florida Artists Hall of Fame. Their determination in the face of adversity remains an important story of perseverance, inspiration and creativity. Early next year, Stars North, a central-Florida–based ­independent-film company, is slated to start production on the film The Highwaymen. Todd Thompson, the film’s writer and director as well as the co-founder of the production company, has wanted to do the movie since moving to Florida more than 10 years ago.

Today, the art and artists enjoy a much larger degree of recognition than they once did. Two of James Gibson’s paintings were featured in Steven Spielberg’s 2002 film Catch Me If You Can, and the collections of former Gov. Jeb Bush and first lady Michelle Obama also include Highwaymen pieces.

The Highwaymen exemplified American ingenuity; they chose not to be paralyzed by their time or circumstance. Instead, through their astounding adaptability, they developed their own aesthetic, which freed them from the mundane. They produced a body of work that has endured and is a ­symbol of determination and entrepreneurial spirit. Best of all, more than 50 years since barnstorming the Florida countryside, their art is finally receiving the praise it deserves.


RON SHIPMON is a New York-based curator and art advisor with 15 years of experience. He is a contributor to several national magazines and is the author of The Mystery of the Stolen Scream.