Beginning in Late 1950s, African American Painters Known as ‘Highwaymen’ Captured Florida’s Natural Landscapes

Untitled and undated painting by Harold Newton

BEGINNING IN THE LATE 1950s, a group of mostly self-taught African American artists devoted themselves to capturing Florida’s natural landscapes. During a time when Black artists were generally focused on figuration and the best way to express themselves in the wake of Jim Crow and the fight for civil rights, they painted windblown palm trees, reflective coastal waters, grassy marshes, crashing ocean waves, and tropical sunsets.

Working in the Fort Pierce area, the artists became known as the Highwaymen. Shut out of museums and art galleries, they asserted their economic independence before and after segregation. Rather than settling for back-breaking work in local citrus groves, they forged a living with their art.

An exhibition currently displayed at the Orlando Museum of Art explores the work of the Florida Highwaymen. “Living Color: The Art of the Highwaymen” presents 100 paintings made between the 1950s and 1980s. The expansive selection showcases choice works by the artists, depictions of Florida’s diverse ecology, scenes that have disappeared over the years, largely lost to development.

(The museum is temporarily closed at least through April 30, due to the COVID-19 virus. Originally scheduled through May 10, the museum has extended the exhibition to Aug. 16, 2020, given the temporary closure.)

Twenty-six artists have been identified as Highwaymen, including one woman—Mary Ann Carroll (1940-2019). Alfred Hair (1941-1970) is considered the founder of the group, and he and Harold Newton (1934-1994) were its leading artists. The two men started painting in their teens and were encouraged by A.E. Backus (1906-1990), a prominent Florida artist and celebrated landscape painter.

Zanobia Jefferson, Hair’s high school teacher, recognized his talent and suggested he seek out Backus, who was white. Newton did the same. They each visited Backus in his studio and he became a mentor, generously sharing techniques and tenets that informed their independent visions.

ALFRED HAIR, “Untitled (Beach Scene with Palms),” n.d. (oil on board, 24 x 36 inches). | © 2017 Doretha Hair Truesdell, Courtesy the Lightle Collection. Photo by Tariq Gibran

Eventually, Hair developed an enterprising system for producing and selling Highwaymen paintings along the highways and roadways of Florida’s Atlantic coast from the trunks of their cars and going door-to-door to doctor’s offices, hotels, and beauty salons. Tourists also appreciated the art. The artists sold directly to clients and collectors who were overwhelmingly white.

The Highwaymen were a loose-knit group, not a formal collective. Although they shared a similar approach—in terms of subject matter, pace of production, and sales strategy—each had a unique visual style. Fast painting was their signature. They did volume business, producing large quantities. Making multiple paintings in one day enabled them to offer their work at affordable prices, about $25 to $35 each. Al Black was particularly gifted at sales.

“I was the salesman for the group when it first started. I went all up and down the highways selling the paintings. If I had 30 paintings that day, I would sell 30 paintings that day,” Black said in a RICHES podcast documentary about the history of Central Florida.

“The only paintings he didn’t sell was the ones you didn’t give him,” Carroll told NPR.

Black drove around in a blue-and-white Ford Galaxy. Sometimes still wet, the paintings would often get damaged. To repair them, Black said he learned how to mix the colors the artists used. Fixing the works, he picked up the skills necessary to compose the landscapes and began making paintings of his own.

Over the years, the artists are estimated to have produced about 200,000 paintings, through the 1970s and more in the decades beyond.

AL BLACK, “Untitled (Indian River view with foreground palm),” n.d. (oil on board). | © Al Black, Courtesy Orlando Museum of Art

THE ENTREPRENEURIAL PAINTERS first became known as the Highwaymen in the mid-1990s. Jim Fitch, a white Florida gallery owner is recognized for coining the name based on their sales method, traveling up and down the highway to find buyers. It was popularized when subsequent news articles about the group invoked the moniker.

Shortly thereafter, around 1996 or 1997, Gary Monroe became aware of the Highwaymen. A working artist and Florida native, Monroe thought he knew everything about the state’s art and culture when he discovered the landscapes. “When I stumbled across these distinctive paintings, I was surprised, humbled and drawn to them,” he told Culture Type by email. “I wanted to understand the artwork and learn about the artists—how the paintings came about and what they might mean.”

A photographer and retired professor of art at Daytona State College, Monroe has authored five books about the Highwaymen.

“At that time there was no scholarship or viable source material.… I had to work through misinformation that was laced with disinformation while getting accepted by the artists, many of whom were not healthy or doing well financially,” said Monroe, who is white.

Based on his research, it was Monroe who determined there are 26 original Highwaymen. His criteria considered self-taught African American artists working in the region in the 1950s, 60s and 70s, who were painting landscapes. The materials they used were a critical factor, too. Highwaymen worked with oil paint on Upson board, an affordable construction material.

“At that time there was no scholarship or viable source material.… I had to work through misinformation that was laced with disinformation while getting accepted by the artists, many of whom were not healthy or doing well financially.” — Gary Monroe

Installation view of “Living Color: The Art of the Highwaymen,” Orlando Museum of Art, Orlando, Fla. (Jan. 24-May 10, 2020). | Courtesy Orlando Museum of Art

His accounting of the members doesn’t sit well with everyone. The “official” list has been questioned by a few artists, both included and excluded ones. Monroe said many Highwaymen had other careers and some would come and go. About 10 artists were committed to the enterprise full time.

Monroe’s first book “The Highwaymen: Florida’s African-American Landscape Painters,” was published in 2001, and Hair and the Florida Highwaymen were inducted into the Florida Artists Hall of Fame in 2004.

Monroe is guest curator of the exhibition at the Orlando Museum of Art. “Living Color: The Art of the Highwaymen” presents paintings drawn from five private collections. Works by Hair, Newton, Carroll, Black, Willie Daniels, Johnny Daniels (1954-2009), James Gibson (1938-2017), Roy McLendon, Sam Newton, Willie Reagan, and Livingston Roberts (1942-2004) are on view. Monroe described the contributing collectors as “seasoned.” They own more than 1,000 paintings among them.

“One collector owns less than 30 paintings. He says he only wants ’10s.’ But two of the other collectors each own about 500,” Monroe said. “One owns 100 and regrets he doesn’t have more wall space at home. Another began his art journey with Highwaymen paintings and went on to collect 19th century Florida art. It’s interesting to see how each person navigates their collection, how they distinguish their collections and themselves by their viewpoints, knowledge, and prowess.”

The most vigorous collectors of Highwaymen paintings are overwhelmingly white men, Monroe said. They bring passion, “prowess,” and competition to the activity. He likens it to “big-time” sports.

HAROLD NEWTON, “Untitled (Crashing Waves on Shore),” n.d. (oil on board, 23 ¾ x 29 ½ inches). | © Harold Newton, Courtesy the Walker Collection. Photo by Tariq Gibran

NEWTON WAS AN EXCEPTIONALLY talented painter and took pride in the artistry of his work. Hair was more concerned with production and turning out paintings in order to maximize sales. In 1970, at the height of their enterprise, Hair was shot and killed in a local bar. He was only 29. When Hair died, it signaled the end of an era. The group’s momentum stalled over the next decade. Tastes changed and the market for their work waned. By 1980, the business went virtually dormant.

The advent of the group’s memorable name helped to raise their profile, and the book and the hall of fame honor sparked a renaissance of sorts. The remaining living artists are painting again, showing their work in local galleries and selling their paintings at weekend meet and greets held in communities throughout Florida.

Doretha Hair-Truesdale, Hair’s widow, paints and preserves the legacy of her husband by sharing the history and origins of the Highwaymen. Carroll, Gibson, Willie C. Reagan, Charles Walker, and Carnell Smith (1950-2015), Hair’s brother-in-law, are among those who continued to paint in their later years and participate in the meet and greets.

Smith started out in 1964 painting the backgrounds—the skies and the water—in Hair’s paintings. By about 1967, Smith was painting his own landscapes. “I was painting whole paintings for him. He had about seven or eight salesmen and me and him and my sister, Doretha Hair would do the paintings and they would do the selling,” Smith said in a 2011 video filmed by Manatee Educational TV (METV) at one of the meet and greet exhibitions.

In 2015, the year he died, Smith talked about his work and the history of the Highwaymen with the South Florida Sun Sentinel. “During those days we were just artists, Black guys painting. We make a living now. Back then we were selling them for like $20, $25, $30, $35 and we made a living back then doing it. It could range from $500 to $10,000 or $15,000 now. Much better. A whole lot better,” he said in a Sun Sentinel video.

“We made more painting than we did picking fruit and tomatoes working in the grove. It was either do that and take care of your family or paint and take care of them. We found out through painting it was a little better and a little easier.”

“We made more painting than we did picking fruit and tomatoes working in the grove. It was either do that and take care of your family or paint and take care of them. We found out through painting it was a little better and a little easier.” — Carnell Smith

MARY ANN CARROLL, “Untitled (Back Country),” n.d. (oil on board, 17 ¾ x 23 ½ inches). | © 2019 Wanda Renee Mills, Courtesy the Jacobs collection. Photo by Tariq Gibran

Carroll, the lone woman in the group, died in 2019. She had been drawing since she was a little girl. When she met Newton, she asked him about the flames on his car. He said he had painted them himself. Newton had a painting in the backseat of his car and when Carroll saw it, she asked if he would teach her how to paint landscapes and he agreed. Carroll recalled the experience in the METV video.

She went to Newton’s house and watched him paint in the yard. He tacked up a 18 x 24 inch Upson board, mixed some paint for her and told her “where to put it.” After some basic instructions, Carroll was on her own.

“It was a challenge. The whole art life was a challenge,” Carroll said. “You go in places where you are not welcome. You’re not appreciated. Some people didn’t talk to you. Well, I guess they talked like they wanted to. Some would say, ‘yes.’ Some would say, ‘no.’ Some was very nice”

She continued: “I found there was as many sweet people out there as there was bitter. I just thank God, basically, for the sweet ones, because everyone that bought a painting put bread on my table, kept shelter over my head, and in the midst of raising seven children, [as a] single parent, they have been momma and daddy, too, for me. I am just more than grateful…”

“It was a challenge. The whole art life was a challenge. You go in places where you are not welcome. You’re not appreciated. Some people didn’t talk to you… I just thank God, basically, for the sweet ones, because everyone that bought a painting put bread on my table, kept shelter over my head,…”
— Mary Ann Carroll

Carroll said it honestly never crossed her mind that what the Highwaymen were doing decades ago was of any significance. For her, it was about survival and having a means to take care of her children. Years later she marveled at the experience and reflected on her approach to painting.

“I don’t do any sketching. I just get the bare board and the paint and start to work,” Carroll said in the METV video. “There have been times I’ve sat down and wanted to paint, but I didn’t have anything in mind. So I go to mixing up some paint. There’s always blues and grays and whatever in the sky. And I say, ‘Okay Lord, here it is. It’s up to you.’ And when it comes out, sometimes it will be some of the best things I’ve done.”

In 2011, First Lady Michelle Obama invited Carroll to the First Lady’s Luncheon hosted by the Congressional Club where the artist presented her with one of her paintings. “I never dreamed of nothing like this.” Carroll said. “She had the nerve to call my name out in front of all those people. I felt like going up under the table. But it was a wonderful thing.”

ALFRED HAIR, “Untitled,” n.d. (oil on board, 30 ¾ x 34 ½ inches). | © 2017 Doretha Hair Truesdell, Courtesy the Jacobs Collection. Photo by Tariq Gibran

TODAY, THE HIGHWAYMEN PAINTINGS are regularly exhibited at the A.E. Backus Museum in Fort Pierce and 18 paintings by various Highwaymen, including Hair, Newton, Gibson, and Carroll, are in the collection of the Smithsonian’s National Museum of African American History and Culture in Washington, D.C., all gifts from Robert and Flory Kahn.

“A goal has long been to see the art of the Highwaymen considered by contemporary fine art scholars and curators. And it’s been a journey,” Monroe told Culture Type.

Years ago, Monroe described how the artists worked and the appeal of their paintings.

“They called it fast painting. Alfred Hair at one time had a studio going. It was a converted porch which he enclosed and put two by fours where he could nail up to 20 boards and he would work on 20 paintings at one time. When the blues were mixed he would do all the skies. Then he’d mix another color and do the ground. Then he’d mix up browns and work on the trees,” he said in the RICHE podcast, describing a process similar to the method Jacob Lawrence used when he painted his narrative series.

“But I should point out, they were never the same. [Hair] never painted the same painting twice. They were all realized in the moment, rather intuitively. They were all described and finished rather differently, but they used the same template and I think that’s because they stripped bare anything that was decorative to arrive at something that was more primal, more about the archetype of the land and its experience.”

Monroe added: “I think that’s largely what resulted in their being so popular. I think that the painterly style worked to their advantage as art and as an inspirational message to these people who were buying these paintings in the 1960s in the afterglow of war and the nascent days of the space exploration, which was happening just up the road for them. It was still good times (for those buying the paintings) and these pictures sort of celebrated the American dream that people were flocking to Florida for to live. It was their version of the American dream with a tropical twist. These paintings, I kind of see as almost like trophies for having arrived in this paradise that was so well described in these paintings.”

“I think that the painterly style worked to their advantage as art and as an inspirational message to these people who were buying these paintings in the 1960s in the afterglow of war and the nascent days of the space exploration, which was happening just up the road for them.… It was their version of the American dream with a tropical twist.” — Gary Monroe

Smith’s tropical images were inspired by the vibrant colors of the sun setting in Florida, particularly during the summer months. The reds, yellows, and greens, he said. The subjects of his landscape scenes included the Everglades and Indian River.

“For years we painted without getting any kind of recognition. We were just trying to make ends meet and make a living and stay off of the streets and things of that nature,” Smith said in 2011. “Had no idea that it would one day, you know, be this big. But, thank God. We made it to this point and it goes to show hard work pays off.” CT

“Living Color: The Art of the Highwaymen” on view at the Orlando Museum of Art in Orlando, Fla, Jan. 24-May 10, 2020 Aug. 16, 2020. The museum is temporarily closed through at least April 30. Check directly with the museum for updated schedules

UPDATE (06/10/20): The museum re-opened June 9 and the exhibition will remain on view through Aug. 16, 2020

TOP IMAGE: HAROLD NEWTON, “Untitled (Man Relaxing on Beached Rowboat),” n.d. (oil on board, 23 ¼ x 35 ¼ inches). | © Harold Newton, Courtesy the Walker Collection

HAROLD NEWTON, “Untitled (Royal Poinciana),” n.d. (oil on board, 21 ½ x 27 ¼ inches). | © Harold Newton, Courtesy of the Asselstine Collection. Photo by Tariq Gibran

Installation view of “Living Color: The Art of the Highwaymen,” Orlando Museum of Art, Orlando, Fla. (Jan. 24-May 10, 2020). | Courtesy Orlando Museum of Art

JAMES GIBSON, “Untitled,” n.d. (oil on board, 22 ¾ x 46 ¾ inches). | © James Gibson, Courtesy the Jacobs collection. Photo by Tariq Gibran

HAROLD NEWTON, “Untitled (Backcountry hammocks at sunset),” n.d. (oil on Masonite board, 22 ½ X 31 inches). | © Harold Newton, Courtesy of the Asselstine Collection. Photo by Tariq Gibran

Installation view of “Living Color: The Art of the Highwaymen,” Orlando Museum of Art, Orlando, Fla. (Jan. 24-May 10, 2020). | Courtesy Orlando Museum of Art

ALFRED HAIR, “Untitled,” n.d. (oil on board, 24 1/4 x 29 1/4 inches). | © 2017 Doretha Hair Truesdell, Courtesy the Lightle Collection. Photo by Tariq Gibran

J. Marshall Adams, director of the A.E. Backus Museum and Doretha Hair Truesdell, talk about her late husband, Alfred Hair, and the Highwaymen art movement he inspired. | Video by Florida Today

Filmed at a Highwaymen meet-and-greet in 2011, Doretha Hair Truesdell, Curtis Arnett, Charles Walker, Mary Ann Carroll, Willie C. Reagan, and Carnell Smith talk about their work. | Video by Manatee Educational TV

Florida Highwaymen artist Al Black talks about spending more than a decade in Florida correctional institutions where he was able to paint during his incarceration. He installed mural-style landscape paintings directly on the walls of the facilities. | Video by NPR

FIND MORE Oxford American and NPR collaborated on a special report about the Highwaymen

FIND MORE about the Florida Highwaymen at Smithsonian NMAAHC

READ MORE about Alfred Hair in The New York Times obituary and Indian River Magazine. His widow, Doretha Hair Truesdell, who says she helped with paintings and made frames, is profiled in Scalawag magazine

READ MORE about Highwaymen women Mary Ann Carroll and Doretha Hair Truesdell. Also read an obituary of Carroll

FIND MORE about Highwaymen painter James Gibson in his obituary, which includes a video about fellow artist Carnell Smith (1950-2015)

BOOKSHELF
An exhibition catalog was produced to accompany “Living Color: The Art of the Highwayman” and includes an essay by Gary Monroe, who guest curated the show. Monroe has authored several other books about the Florida Highwaymen, including “The Highwaymen: Florida’s African-American Landscape Painters” and volumes about key individual figures in the group—“Mary Ann Carroll: First Lady of the Highwaymen,” “Harold Newton: The Original Highwayman,” and “The Highwaymen Murals: Al Black’s Concrete Dreams.” Another publication, “Alfred Hair: Heart of the Highwaymen” is forthcoming in September. In addition, “Florida’s Highwaymen: Legendary Landscapes” by Bob Beattyl provides an overview of the Highwaymen.