Quieter side of the Highwaymen

Against All Odds: The Art of the Highwaymen

Against All Odds: The Art of the Highwaymen

Through Jan. 2 at Orange County Regional History Center
65 E. Central Blvd.

About 15 years ago, historians, writers and collectors discovered the work of a group of African-American men now known as the Florida Highwaymen. The work of these young artists – some more talented than others – dates back to the 1950s and ’60s, when the impoverished entrepreneurs figured out that they could make money by selling paintings created in assembly-line fashion on the side of Florida’s roadways.

Using whatever material was available for cheap – house paint on Upson board, and later Masonite, was common – the Highwaymen painted idyllic interpretations of Florida landscapes: palm trees blowing in the breeze, flowing rivers, ocean waves hitting the shoreline and resplendent sunsets. The paintings always featured a light shining from above, be it sunshine, moonlight or something more divine. The goal of the Highwaymen’s enterprise was to make money, and it did: The Florida Division of Cultural Affairs estimates that there are some 200,000 Highwaymen paintings in circulation, but no one knows for sure because there was no documentation.

In 2004, the Florida Highwaymen were inducted into the Florida Artists Hall of Fame, and paintings that once sold for $15 to $45 to travelers and businesses were now valued as high as $45,000, depending on the artist and the year the piece was created. The paintings are highly collectible – especially those done by the nine core members thought to be the best of the group, including Alfred Warner Hair (1941-1970) and Harold Newton (1934-1994).

The Against All Odds: The Art of the Highwaymen exhibit at Orange County Regional History Center de-liberately includes paintings by all 26 artists thought to be affiliated with the group, including one woman, Mary Ann Carroll. The paintings are from the private collection of Geoff and Patti Cook and were selected so that at least one piece by each of the 26 artists is represented.

Compared to previous exhibitions of the Florida Highwaymen that feature the signature bright and loud colors, the palette in Against All Odds is relatively subdued, save for the flaming-red blooms on poinciana trees that appear in several pieces. This was intentional, says Cipolla, who worked with the Cooks to present pieces by all of the 26 recognized Highwaymen as individual artists and not just the road-side landscapes they created for travelers who wanted to bring a bit of Florida home with them. Two unusual pieces on display deviate from the stereotype: Hezekiah Baker’s scene of black workers in a cotton field and Robert Butler’s scene of a paddle wheel docked on a shore with a white lady under an umbrella accompanied by a suited gentleman.

On Nov. 20-21, the Orange County Regional History Center will host a “Highwaymen Weekend,” during which members of the Highwaymen will be on hand to discuss their craft. The event will show contemporary works created and promoted by the progeny of some of the founding members of the group. Many of these paintings recall the entrepreneurial roots of the Highwaymen tradition. The new pieces are not as valued as original paintings from the 1950s and ’60s, but they keep the story of the Highwaymen alive.


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