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Who Were The
Florida Highwaymen?

an interview with author Gary Monroe

by Andrew Elias

















SOME 50-60 YEARS AGO, residents and travellers alike, could find African-American artists selling their landscape paintings out of the trunks of their cars along the highways of Florida, mostly around the Fort Pierce area. Working in their garages and barns, these artists had no formal training and often used construction materials rather than traditional art supplies. Their success in the Jim Crow South and during the civil rights movements is a testament to the allure of their romantic visions of the Florida paradise.

Gary Monroe is one of the leading experts on the Florida Highwaymen, writing several definitive books about this historic group of distinctly American artists.

The Southwest Florida Museum of History will be hosting an exhibition of Highwaymen paintings, ‘Sons of the Sun,’ September 5-January 3, including several works from private collections that have not been seen by the public. There will be an opening reception attended by three surviving Highwaymen (two men and the only woman). Monroe will be making a presentation about The Highwaymen in November.

I asked Monroe about The Highwaymen and the upcoming exhibition.

For people who don’t know... Who were The Florida Highwaymen? And what made them special?

The Highwaymen were a loose association of young African Americans who, from roughly 1960-1980, painted their way out of the orange groves and packing houses into creative, lucrative and fulfilling lives. All but one of the painters, Alfred Hair, were self-taught. Hair had taken painting lessons while in high school, and he’s largely responsible for the assemblage of these 25 men and one woman who decades later would become known as the Highwaymen.

To say that they beat the odds is an understatement. In a time in our history when African Americans lived as second-class citizens, these young people were undeterred by Jim Crow laws and traversed the state during the thick of the Civil Rights era, selling their artwork with aplomb to a white clientele. The Highwaymen left the visual legacy of modern Florida. Some 200,000 of their oil paintings graced homes and offices, symbolizing the aspirations of Floridians and emblematic of what the state meant to Americans – a land of renewal and reward.

When did you first become aware of The Highwaymen? And what about their paintings or story drew you to them?

I learned about the Highwaymen while doing the research for my book, Extraordinary Interpretations: Florida’s Self-taught Artists. Nameless during their tenure, they had just been dubbed the Highwaymen by my friend Jim Fitch. There was neither scholarship nor reliable facts to discern their history then. I decided to put the pieces together, and Jim gladly and gracefully passed the torch. I didn’t quite know what I was getting into, that I would need to wade knee deep in rumor and innuendo, through misinformation and even disinformation, before getting the story straight and offering an informed critique of the artwork.

Laced with pathos, the Highwaymen’s story is a flawless one of transcendence, a quintessentially American tale of determination, ingenuity, hard work and more. It seems to be an unlikely story and the painters the unlikeliest of artists. In fact, I argue that the Highwaymen’s style of fast-painting led to a new and fresher form of landscape art than had been the popular model. With enough tenacity and sets of car tires, anyone could have told their story; my sustaining interest was with interpreting the nature of their art.

Why do you feel The Highwaymen are an important part of American art history?

The way they painted led to their style or form of painting. The bottom line is this: they were barely 20-somethings and most were driven to live fast and make lots of money. That was how they kept score, so to speak. Painting was the means to the end of living well, if not large, while enjoying their youth. In the first book, The Highwaymen: Florida’s African-American Landscape Painters, I wrote that they became artists by default. Living fast and large was expensive and they knew that being excluded from the established art market meant they would have to sell their paintings for less money than they would otherwise be worth – about a tenth of the value.

To make up for the shortfall, Alfred Hair reasoned that he’d have to complete ten paintings in the time that it would take professional artists to paint one canvas. He did not bargain for the fact that, by doing so, he would corrupt the accepted ways; that he would, through painting fast, realize a new kind of landscape imagery, one that favored suggestiveness over precisely described detail.

The paintings of The Highwaymen are sometimes called folk art or ‘outsider’ art or even ‘naive’ art? Do you agree? What is meant by ‘outsider’ art?

Contemporary folk art is an umbrella term that generally accounts for naïve and Outsider art; folk art otherwise refers to tradition-bearing crafts such as quilting and sign making. Today’s folk artists are self-taught, but the Outsider designation suggests that the artist works without regard to much of anything but his or her own imagination; idiosyncrasies generally lead the way. It is fascinating art that often challenges status quo beliefs. I’m not certain where the Highwaymen fit in this scenario. They seem to be in class of their own.

The Highwaymen were almost exclusively men. Tell me about Mary Ann Carroll, the only woman in the group, who you’ve written a book about, which will be published in October.

Mary Ann Carroll: First Lady of the Highwaymen is a labor of love. I planned to stop writing books about the Highwaymen with the third book in the series. Although Mary Ann and I had become very close, I declined when she asked me to tell her story in a book, but when University Press of Florida, which publishes my books and whose director, with whom I had a pleasant working relationship for a decade, asked me to do it, I felt compelled. I thought the Mary Ann book would be the easiest to write; I’d already done the heavy lifting but, in reality, it turned out to be the most difficult. All I knew about her and the other Highwaymen artists led me to explore the times during which they came of age and to describe the obstacles they faced as they traveled around Florida hawking stacks of still-wet oil painting to white people. The book explores the Jim Crow environment in which the artists painted and prospered, and it pivots around Mary Ann’s biography, the single mother of seven children who founded her own church, all the while painting. As she put it, she had mouths to feed and “it was an honest dollar for an honest day’s work.”

Three original Highwaymen — Al Black, James Gibson and Mary Ann Carroll — will be attending the opening reception for the exhibition. How do they feel about the renewed interest and acclaim The Highwaymen are receiving of late?

The initial meeting I had, more than 15 years ago, was with James, Mary Ann and Hezekiah Baker (deceased); Al’s certainly the most colorful and intriguing of the remaining Highwaymen. They well represent the Highwaymen, as these are three of the core members, of which there are eight. None of the Highwaymen expected the cultural phenomena that we are seeing today. They were content with having worked in the shadows; they made money and had good times. It was in the past and when it was over they went on their ways. But their warm welcomes and their art having iconic status is testimony to their paintings striking a chord among us Floridians.

A few paintings in the ‘Sons of the Sun’ exhibition at the Southwest Florida Museum of History will be on view for the public for the first time, from private collections. Tell me about the paintings, the collections and the collectors.

Collectors of Highwaymen art feel that they acquired paintings that were made with them in mind; they personalize the quintessential but generalized Florida scenes. They may swear that they know the exact location from personal experience. About the same painting, one might hear (as I have) that “This is the bend in the St. Johns River where I caught my first Bass when I was 12-years-old, and I’ve been collecting Social Security for more than a decade,” which might compete with, “This is the spot along the Banana River where 56 years ago I used to park the ole Chevy with my wife of 55 years.” That’s the nature of this art. It’s largely because of the artists’ fast-painting, which stripped artifice bare to leave an archetypal image. Whether a collector has one or 100 Highwaymen paintings, their holding mean a lot to them and express their understandings of the Florida experience. The paintings have a way of finding their ways to the rightful owners.

Some of The Highwaymen were real characters, like Alfred Hair, who is cited as the founder or leader. Can you tell me about him?

There are two ways to approach the Highwaymen story – through Harold Newton and through Alfred Hair. Both ways are virtuous; both are right. But Hair’s art and life offer a wellspring that allows for fresh ideas to be explored. His was a beautiful life with a tragic ending, and I was proud to tell the story. The first book is dedicated to him. Hair was said to be movie-star handsome and unquestionably charismatic, a larger-than-life figure without ego or attitude.

What will you be speaking about at your presentation in November?

This story needs no embellishment, so I’ll tell how the group formed, how they painted and played, and offer a view of how the artwork functioned and why the paintings sold before the oils had time to dry. It’s a compelling story – not even Steven Spielberg could improve on it. Of course I’ll survey, via Powerpoint, the artists, tell a bit about each of them as I show their most colorful paintings.

Why should art lovers and history buffs go and see the ‘Sons of the Sun’ exhibition?

There’s a presence to these paintings that are lost to reproduction, and under their glow people can’t help but relate, to lend their own meanings and become part of the art equation; this leads to reflection on things that matter. The Highwaymen’s art, you’ll see, is not merely decoration. •

‘Sons of the Sun: The Highwaymen’ will be on view at the Southwest Florida Museum of History, September 5-January 3. There will be an opening reception September 5, 5:30-7:30pm, free to the public. Gary Monroe will be making a presentation, ‘Painting Paradise: The Art of The Highwaymen at the Museum on November 7, 5:30pm. The reception and presentation are free. The Museum is open Tuesday-Saturday, 10am-5pm and is located at 2031 Jackson St. in downtown Fort Myers’ Historic River District. For information, call 321-7430.


Gary Monroe, author of several books about the Highwaymen, including The Highwaymen: Florida’s African-American Landscape Painters, recognized by The Original Florida Highwaymen as “the official book about the Highwaymen.” For more about The Highwaymen, visit his website: www.floridafolkart.net.


September-October 2014



painting by Robert L. Lewis



painting by Alfred Hair



painting by Harold Newton



painting by James Gibson




painting by Harold Newton