By 
Anyone who’s ever taken an interest in the Florida Highwaymen has wondered about Florida Highwaymen art for sale. With an estimated 200,000 paintings produced during their peak from the late 50s through mid-1970s, one of those – or more – should have your name on it. Better yet, a handful of the 26 original Florida Highwaymen, which included one woman, are still painting.
“Al (Black) will make a phone call, he’ll be like, ‘Hey, I got some pictures, you want them?’” Kelvin Hair, son of Highwaymen original Alfred Hair and a second-generation painter from the group, told me on my “Welcome to Florida” podcast. “Sometime people (are) like, ‘yeah, how many you got?’ ‘I got like 12.’ ‘Well, bring them over to me.’ He’ll sell them all.”
Therein lies the rub.
Nowadays, Florida Highwaymen art for sale isn’t so easy to find. The remaining original members have long-time customers who purchase much of their new work. Their increasing fame as a group collectively elected into the Florida Artists Hall of Fame in 2004, along with numerous subsequent museum exhibitions and books about their work, has mostly ended the days when Florida Highwaymen art could be found cheap in yard sales around the state, castoffs of clueless homeowners.
Florida Highwaymen art for sale can be found through specialty retailers online, most notably Highwaymen Art Specialists, Inc in Vero Beach. Highwaymen historian and super-collector Roger Lightle owns the business which operates out of his home. I stopped by to visit him early in 2022.
Anyone interested in purchasing Florida Highwaymen art for sale in person should take advantage of Lightle’s hospitality.
I’m generally leery of buying artwork online from ebay and individuals I don’t know. For one thing, with so many genuine Florida Highwaymen paintings in the world, rest assured, there are a large number of fakes to accompany them. The Highwaymen learned to paint fast and cheap which makes their work ideal for copying. Fortunately, the Highwaymen market hasn’t been inundated with forgeries like other segments of the contemporary art market, still, there’s a greater risk in being duped when you purchase online.
When thinking about Florida Highwaymen art for sale – or any art – I like connecting a face and a name with my purchase. That’s why I prefer buying art for my personal collection direct from the artist or from a respected gallery with a history of sales, a brick and mortar retail location, a phone number and website and gallerist or owner with a face and a name – like Roger Lightle – to back their sales.
One Vero Beach auction house which regularly sells Highwaymen paintings on-line I did visit in person: Vero Beach Art Auctions. I met the owner David Kratzer, walked through the warehouse, talked to him about the Highwaymen and fakes, looked over the pictures he was selling at the time, and came away impressed by his honesty.
How the Highwaymen got their name
The Florida Highwaymen were painters of necessity. Painting was a professional choice more than a calling, and as much as they loved it and did have a talent for it, their primary motivation for painting was to avoid hard labor outdoors in the Florida citrus groves picking fruit during the Jim Crow era.
Florida Highwaymen art for sale was always intended as a means to an end. That end was feeding their families and putting a roof over their heads.
To do so, they had to be creative beyond the fantastical images they conjured.
“My dad realized that he, being a Black man, wasn’t getting the type of money that a white artist would. He wasn’t getting to go to the art shows like they would, so what he did was, he developed a faster way to paint, and he painted cheaply so he could still make a profit because back in those days, a canvas and a frame was pretty expensive and that would not allow you to be able to sell a painting for $20 – you’d lose money,” Kelvin Hair explains of his father Alfred, who died at just 29 years of age, shot dead in 1971 during an argument in a pool hall. “He started painting on a building material that they used in houses, almost used like drywall is today, it was a compressed cardboard. It was called Upson board and you get a four-by-eight (foot) sheet for a little under $2. Then he’d use crown molding which you see along the baseboards of your house to make the frames. So, he had his ‘canvas’ and his frames relatively inexpensive so he could still sell a painting for $25 bucks and still make a profit.”
Shut out of the galleries, long before the internet, the Highwaymen further innovated by taking their artwork on the road, selling paintings from the trunks of their cars along U.S. 1 near their home base in Ft. Pierce on the Atlantic Coast about midway between Daytona Beach and Fort Lauderdale and hiring salesmen to cover the state doing the same.
That’s where the Highwaymen name comes from.
Even into the 2000s, Highwaymen sold their paintings this way. Kelvin Hair recalls hitting the road on many of these trips with original member Al Black – and how successful they were.
How much are Highwaymen paintings worth
Sticking with Alfred Hair, who along with Harold Newton are the most prominent members of the original Highwaymen, the increasing value of Florida Highwaymen art for sale is extraordinary.
Again, remember, the Florida Highwaymen were volume painters. They couldn’t sell their paintings for much and they had to exist on what they sold, so they painted fast and dropped their prices.
“My dad would probably be amazed at the price that some of his paintings fetched,” Kelvin Hair told me. “Paintings that he probably sold for $50, $60, I’ve seen them go for $30,000, $40,000, $20,000 as a common price.”
The best of the best from Alfred Hair and Harold Newton can now fetch over $100,000.
While you don’t have to spend five figures to purchase Florida Highwaymen art for sale, you aren’t likely to find anything under $1,000 anymore either, particularly anything from the original members, old or new. A good price for a large – 24 inches by 36-inch range – authentic Florida Highwaymen painting from an original member painted during the prime decades of the 50s through the 70s will cost in the neighborhood of $5,000 depending on the artist, the image (especially popular are Florida Highwaymen poinciana paintings), the condition and other factors, like if it is signed. Smaller paintings in the 12”x24” size can be found for just over $1,000.
Cheaper prices exist on ebay and other such online auction sites – a friend of mine bought a splendid Hezekiah Baker from ebay that has the look and feel of an authentic painting for $900 in late 2021 – but again, the risk there for fakes and scams is real.
Prices for artworks from original Florida Highwaymen have gone up dramatically in the last 20 years since the group started regaining attention. Twenty years ago, six-figures for a Highwaymen painting would have been almost unimaginable. It’s a safe bet the sales records will continue in that direction.
“I’ve talked about this with serious, serious art collectors and serious, serious dealers. Here’s the thing, right now, you can still go to Al Black and buy a painting, you can still go to Roy McLendon and buy a painting. You can still go to some of the other artists that are still living and get an original Highwayman painting,” Kelvin Hair said. “All of the Highwaymen are really up there in age, what happens when the last living Highwaymen, the original, is gone? Now, for (you) to buy that painting, guess what, (you) got to come and buy it off (someone’s) wall. What are you going to charge? It’s going to cost an arm and leg. Prices are going to really zoom up when you have to go and get it off somebody’s wall.”
Dominick Alesandrini
April 19, 2022My wife, son and I visited the Tampa History museum several years back when they had the Highwaymen exhibit. Being an amateur art collector but a life long admirer I knew about the Highwaymen and their back story. I had seen many of the artist’s works on line and in books , but until you are standing 2 ft away from their work you just can’t really appreciate the pieces. I moved to Florida in 1971 as an 11 year old boy , but I first visited in the late 60’s. The Florida I remember from those days came back to me through the paintings by the Highwaymen. It’s not uncommon to stand in front of a piece and just look at it for 10 minutes or more. For me, the visit to the museum to see this exhibit was an unexpected and touching trip back in time. Before Florida was what it has become. The Highwaymen were all so very talented and I hope that more people will visit the exhibits and learn from the works. What it was like to be an African American artist before the days of civil rights and how we should cherish the work that all of these amazing artists created.
Chadd Scott
April 20, 2022Love hearing stories like yours about the impact of the Highwaymen.