Growing up in a home filled with paintings and paint supplies provided me with a deeper understanding and appreciation for art.  Canvases lined our back room.  Some were framed and finished.  Some were not.  Those paintings stood waiting for that one extra paint stroke to be added to a tree, a river, or a deer. I didn’t realize it at the time, but one of those paintings was done with the instruction of Robert Butler, a Florida Highwayman, at a day-long class that my mom, Nancy, took in 1990.

Painting by Nancy Collins (Mom) under the instruction of Robert Butler

Signature, Instructor Robert Butler, 1990

Mom remembers the painting class from 28 years ago at a local art studio like it was yesterday. “He painted from his head,” she says, “from memory of things he had seen.  He taught me a lot about painting Florida landscapes.”

Butler passed away in 2014, and like other Florida Highwaymen, left an indelible mark on many artists and art lovers.

The Highwaymen – Then

Although they did not acquire the name “The Highwaymen” until years later, the group consisted of 25 men and one woman, all African-American, who painted Florida landscapes from the mid-1950s through the mid-1980s.

Inspiration for these artists initially came from A.E. “Bean” Backus, a popular landscape artist at the time.  One of the founders of the Highwaymen, Alfred Hair, met Backus during a school field trip to his studio, went to work for him building canvases, and learned to paint. Hair took Backus’ techniques and tweaked them to meet his own needs of making money in a short period of time.

Carports, sheds and backyards in the Fort Pierce area served as painting studios.  Upson board, a popular building material at the time, and oil-based paint were the supplies of choice.  At a time when segregation was the norm, galleries would not accept their paintings, so the artists sold out of their trunks along Florida highways – mostly on A1A and U.S. 1 from Daytona Beach to Miami – and door-to-door to motels, doctors’ offices, banks, real estate offices and other businesses.  The paintings brought in about $20 each and provided an alternative to working minimum wage jobs or picking citrus.

Highwaymen paintings all exhibit the same characteristics: Florida the way it was before development took over.  Vibrant red Poinciana trees, moss hanging from cypress trees, and palm trees swaying in the breeze of a calm summer day or blowing during a raging Florida storm are the subjects of many of the paintings.  So too, are sunrises and sunsets, marshlands and native Florida wildlife.

The Highwaymen – Now

Of the original 26 Highwaymen, only half are still living, some of them still appearing at events around the state.  At a recent Meet and Greet at the Orange County Regional History Center, six of the original artists displayed and sold their paintings, posed for photographs and signed autographs.

Al Black

Al Black and Doris Keeler (Writer/Blogger)

Al Black, 71, was the original “salesman” for Alfred Hair.  In the early days, Black did not want to paint – he wanted to sell, and that’s what he did.   He loaded Hair’s paintings up in his car, often wet, and went on the road to sell them.  Because the paintings were wet, they were sometimes damaged in the trunk and Black would touch them up before selling them.  That led to his own interest in painting, and after Hair’s death, he painted and sold his own artwork.

The journey has not been easy for this Highwayman.  In the 1980s, the demand for the paintings dried up and Black got caught up in cocaine.  After an arrest and conviction, he spent 12 years in prison.

“When I first went in, I was coming out in the papers.  Everyday I was in the paper,” Black says. “The warden walked up to me and said, ‘are you Al Black, the one I’m reading about in these books?’ I said, ‘Yes sir!’”

That one question and answer led to Black painting more than 100 murals on the walls of the Central Florida Reception Center in Orange County and the Tomoka Correction Institute in Daytona Beach.  His talents were also requested at the Zephyrhills Correctional Institution, and he went there to paint for them.

Black was released from prison in 2009, during which time he says he found God.  His later paintings all have one thing in common – three birds, representing the Trinity.

A small sampling of Black’s paintings. Do you see the three birds in each one?

Today he lives in Fort Pierce, paints and travels with the others.  He is quick to strike up a conversation, but when someone is wanting to buy a painting, that takes precedence, and he stops to sign his work. Even now, Black is surprised at the notoriety of the Highwaymen.

“I never thought it would be like this.” 

Al Black stops to sign a painting purchased at the show

Mary Ann Carroll, “Highwaywoman”

Mary Ann Carroll at her display

Mary Ann Carroll is the only female in the Highwaymen, but she says that doesn’t bother her. “I don’t feel like a queen. I don’t feel any different, I just feel alright,” she says.

Carroll, now 78, remembers those early days well.  She was taken in by Harold Newton and Livingston “Castro” Roberts, who she says she could talk to anytime about anything.  Carroll is grateful for the ability to paint.

“I just thank God for the gifts he gave me. I was blessed coming up.  I didn’t know I would have to raise my children as a single parent.”

Carroll sold her first painting when she was 18 years old. Although Al Black would take some of her paintings on the road, she would often go solo and sell them herself.  Like other Highwaymen, her paintings feature Florida sunsets, waves crashing onto the beach and palm trees, all in vibrant colors.

Collage of Carroll’s paintings on note cards

Besides painting, Carroll also had other jobs to help support her family, including carpentry and house painting. Today, Carroll lives in Fort Pierce and makes appearances at various events around the state.

 Robert Lewis

Robert Lewis is one of the more active Highwaymen and can often be found at community events. While his paintings on display are a sight to behold, the biggest attraction is watching him put brush to canvas. An easel holds a current painting he is working on – a landscape with trees, a dirt path, and a pond.  One of his fans, who has undoubtedly met him before, tells him the left side of the canvas is a little barren.  After looking at it, he agrees and paints in another tree.

Robert Lewis surveys his painting

Lewis adds in a tree at the advice of a fan

While most of the other Highwaymen were self-taught, Lewis graduated college in 1966 with a degree in art education and went on to teach art in school and in college. He never painted with the Highwaymen but knew several of the members and painted on Upson board like the others. Because of his education, his paintings include more wide-ranging subjects than others.

Someone in the crowd that has gathered around to watch him paint says, “You look good.  What is your secret?”

Lewis answers quickly, “I paint!”

 R.A. Roy McLendon

Once an artist, always an artist, and at 86 years old, Roy McLendon still paints. His wooden easel reveals years of paint choices and color mixing.  His paintings reveal more than just landscapes and nature.  They portray people as being a part of the landscape.

McLendon includes people in his landscapes

Tools of the trade

At 86, McLendon continues his painting

Curtis Arnett

At 68, Arnett is one of the youngest of the Highwaymen.  With an early interest in art, he began experimenting with paint after a visit to his high school by Alfred Hair. Arnett also got to know Bean Backus and later Robert Butler. Unlike other Highwaymen, Arnett painted with acrylics instead of oil-based paint.  His paintings feature hammocks, swamps and cypress trees.

Curtis Arnett, Photo Courtesy of www.TheHighwaymenTrail.com

Isaac Knight

Isaac Knight sits to the side of his display of large and small paintings. Like fellow painter Al Black, Knight started out selling paintings, but discovered there was more money to be made in painting and selling his own.  He and Black painted what they saw the others painting and used tips they received from Bean Backus to create their own landscapes.  Although he still likes painting with bright colors, Knight’s signature style is now his black and white paintings.

Isaac Knight with paintings

From Roadside to Gallery

The Highwaymen’s paintings offer glimpses of Florida many people will never experience – open spaces, wildlife roaming freely.  Some of them still paint every day, others a few times a week. Their shows are well-attended, by those curious about the Highwaymen, or those who are knowledgeable about the art and the artists.

Times have certainly changed.  Paintings that were once sold along the side of the road for $20 – $30 are now selling for thousands of dollars in galleries and antique stores.  What started as a group of painters just trying to make a living has evolved into an era in Florida’s art history that spanned a 30-year period with more than 200,000 paintings.

Additional Highwaymen Resources

The Highwaymen Heritage Trail – A trail in Fort Pierce that features 10 stops of significance to the Highwaymen.