The Legacy


The Florida Highwaymen are a group of 26 African American landscape artists in Florida. Self-taught and self-mentoring, they created a body of work of over 200,000 paintings, despite facing many racial and cultural barriers. Mostly from the Fort Pierce area, the artists painted landscapes and made a living selling them door-to-door to businesses and individuals throughout Florida from the mid-1950s through the 1980s. They also peddled their work from the trunks of their cars along the eastern coastal roads (A1A and US 1).

2003-31gibson-300x201For over 50 years, the Highwaymen created large numbers of relatively inexpensive landscape paintings using construction materials rather than traditional art supplies. As no galleries would accept their work, they sold them in towns and cities and along roadsides throughout Florida, often still wet, out of the trunks of their cars. Their success and longevity is remarkable considering they began their career in the racially unsettled and violent times of the 1950s in Florida and amid the social conditions of the Jim Crow South where the stirrings of the civil rights movement were only just beginning. They have been called “The Last Great American Art Movement of the 20th century.”

Highwaymen Induction Ceremony

In the 1950s and 60s, it was impossible to find galleries interested in selling artworks by a group of unknown, self-taught African Americans. Instead they sold their art directly to the public rather than through galleries and art agents. Rediscovered in the mid 1990s, they are recognized as an important part of American folk history.

Med MedallionIn 1970, one of the original members of the group, Alfred Hair, who was also considered to be the main catalyst and soul of the group, was murdered. Subsequently some of the group’s creative energy and direction were lost. the remaining members created fewer paintings, and productivity waned. However the artists were re-discovered in the mid 1990s by Jim Fitch, a Florida art historian, and Jeff Klinkenberg of the St. Petersburg Times wrote several newspaper articles about the Florida Highwaymen in August 1995. Since then, they have become celebrated for their idyllic landscapes of natural settings in Florida. The 26 Florida Highwaymen were inducted into the Florida Artists Hall of Fame in 2004.

The rebirth grew internationally during the 2000s and they have become a recognized part of Florida culture and history. The remaining artists in the original group continue to paint to this day. Over time, their style has evolved into more carefully created works away from the original “fast painting” techniques that enabled them to produce large quantities of paintings in their early years.
Hwy-OriAnalogies compare the Hudson River School of the mid 19th Century and Group of Seven (artists) from Canada in the early 20th century to The Florida Highwaymen Artists. In their respective times, these groups mentored and created works collaboratively. Painting en plein air style, these groups of artists created expansive landscapes of untouched and pristine lands, creating scenes of timelessness and raw natural beauty. In many ways the Florida Highwaymen’s story is even more compelling and romantic than the other groups, as the Highwaymen had no backing or support and were much more resourceful and creative in both production and sales of their works.

Group2The Florida Highwaymen were influenced by Florida landscape artist A.E. Backus during the 1950s-80s (although only Alfred Hair was a formal student of Backus). His influence extended through Hair and Harold Newton to the other twenty-four artists in the group. Some in the formal art world have given this group and its followers the name “Indian River School,” but they are most well known as the Highwaymen. Not known as “highwaymen” in their heyday, the name was bestowed by Florida art collector and museum curator, Jim Fitch, in a 1995 article in Antiques and Art Around Florida.

The Highwaymen were mostly self-taught painters, who mentored each other. Excluded from the traditional world of art shows and galleries, the Highwaymen painted on inexpensive Upson board or Masonite and framed their paintings with crown molding (brushed with gold or silver paint to “antique” them). They packed these paintings into the trunks of their cars and sold them door-to-door throughout the southeastern coast of Florida. Sometimes the paintings were stacked before the oil paint was dry.


Paintings by the Florida Highwaymen are prized by collectors today, but their story is about much more than art. Today their 200,000 plus paintings have gathered significant interest and have become quite collectible. At auctions some of these particular painters’ works have been recognized with high prices, notably important older works by the “original” members.

It was not a formal movement and represented no “official” group, yet the Highwaymen thrived as artists and entrepreneurs through their sheer determination to succeed as painters and not as laborers in citrus groves, their expected social role. The works are also classified as “Outsider Art,” or “Folk Art.” They honed techniques to rapidly produce their paintings and developed strategies to sell and market their artwork outside of the formal world of art galleries and exhibitions. Their story is one of African Americans who carved out unique economic opportunities despite the social conditions of Jim Crow.

HaroldNewtonartIn 2000, twenty-six artists were identified as Highwaymen. These artists were inducted into the Florida Artists Hall of Fame in 2004 as the Highwaymen and include: Curtis Arnett, Hezekiah Baker, Al “Blood” Black, brothers Ellis and George Buckner, Robert Butler, Mary Ann Carroll (the only woman in the group), brothers Johnny and Willie Daniels, Rodney Demps, James Gibson, Alfred Hair, Isaac Knight, Robert Lewis, John Maynor, Roy McLendon, Alfonso “Pancho” Moran, brothers Sam, Lemuel and Harold Newton, Willie Reagan, Livingston “Castro” Roberts, Carnell “Pete” Smith, Charles Walker, Sylvester Wells, and Charles “Chico” Wheeler.

Of these twenty six, nine are considered “original” (or the earliest) Highwaymen. Harold Newton, Alfred Hair, Roy McLendon, James Gibson, Livingston Roberts, Mary Ann Carroll, Sam Newton, Willie Daniels, and Al Black.

Newton ptg

In 2008, an hour-long PBS-TV documentary film was released called “The Highwaymen: Legend’s of the Road.” It was produced by father and son team Jack and John Hambrick (both veteran TV news journalists). 

Most of the living artists are active and aggressively marketing their newer works. Many of the earlier paintings are signed, but there are a number of paintings that weren’t, there are a number of paintings that are sold as “Highwaymen Style” that emulate the iconic landscapes of the Highwaymen artists, but are indeed just mere reproductions with little real value. Older paintings from the 1950s and early 60s era are more sought after by collectors.