The Florida Highwaymen

The Florida Highwaymen, as they became known, were a group of African-American artists who sold their paintings out of the trunks of their cars. They often parked on the shoulders of Central Florida highways in order to paint the idyllic 1950’s Florida landscape that, pre-Disney, was full of cypress swamps, lush orange groves, and thick mangroves.  During their heyday, the Highwaymen sold their paintings for anywhere between $20-$35 to tourists and snowbirds who were eager to take a piece of Florida home. These young black men (and one woman) defied society’s expectations that they were only useful for picking oranges from the groves and managed to make a meager living selling their artwork instead.  Because of the racial instability that plagued the southern states, the Florida Highwaymen knew their works would never be accepted as real art, so to make more money they worked in quantity rather than quality.

artist: Livingston Roberts

artist: Alfred Hair

This was Florida in mid-century and the state was often overlooked by the rest of the country when one thought about the Jim Crow south. Its swaying palm trees and magnificent sunsets were indicative of paradise, not racial rioting and lynch mobs. I’m learning now that Florida actually holds the highest recorded number of lynchings, more than any other state in the Deep South. I am currently reading Gilbert King’s book Devil in the Grove, a true story about four young black men, referred to as The Groveland Boys, in Central Florida charged with the alleged rape of a white teenager, and I am even more astounded that the Highwaymen would challenge the race standards set by the majority of small-town politics and the County Sheriff/Ku Klux Klan relationship to carry out what some have called “the last greatest art movement of the 20th century”.

I am not surprised, however, to learn that a film company is desperately working to make their story into a movie. The production company’s fundraising efforts haven’t collected nearly enough to get this film out anytime soon, but I can tell you that the first draft of the screenplay was completed on June 1st.  You can watch a very short movie trailer here.

Last summer, I was fortunate enough to meet a few of the Florida Highwaymen at a gathering in a local antique mall – Carnell Smith, who signs his artwork as C. Smith, and Robert Lewis, who signs his paintings as R.L. Lewis.  Also in attendance was the only female painter, Mary Ann Carroll.

with C. Smith

with Carnell Smith

with Robert L. "R.L." Lewis

with Robert L. Lewis

Robert Lewis took an immediate interest in Elle, our family’s budding artist. I doubt she really understood the significance of her encounter with this man, but I love that he told her how important a good education is since he was an art teacher for the majority of his life. Most of the Florida Highwaymen have never gained and will never gain individual fame and fortune from their artwork – Alfred Hair, an original Highwaymen painter, was shot and killed in a confusing gunfight in 1971 and another Highwayman, Al Black, is currently serving a jail sentence and painting murals for the state prison in which he’s incarcerated. The rest of the Florida Highwaymen make the rounds and meet their fans, new and old. Those paintings that used to sell for $20 now go for a few thousand bucks.

It is my new big wish to own a Florida Highwaymen painting.


About Dena

I'm a suburban Clevelander by way of Oklahoma City, by way of North Florida, by way of Southern Maryland, by way of Upper Michigan, by way of Northern Italy, by way of Lower Michigan, by way of Texas. Because of living in so many places, I have something in common with almost everyone I meet. I love reading, writing, and American history (especially reading or writing about American history). I'm interested in culture of place, historical trauma, and writing about the kinds of histories most people don't know about.
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2 Responses to The Florida Highwaymen

    • Dena says:

      My mother owns a few small ones. She’s been aware of them since she was a kid, but only now are they fairly easy to come across, once you know what and who you’re looking for!

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