The Highwaymen: Segregation-Era Florida Artists Sold, and Often Painted, by the Roadside

Orange Sky, Breaking Surf, 3 Birds by Alfred Hair (1941 - 1970), ca. 1965, oil paint on fiberboard

Perhaps the art of the Highwaymen can best be described as a marriage of rich arresting color and stark simplicity of form. If the viewer lets his or her imagination soar, the effect is almost hypnotic—these scenes appear to be embedded in time.

EDNA WEISSMAN Art Link International

Renowned for their resourcefulness, speed and creativity, a group of Florida artists known as the Highwaymen employed a unique painting style as a way to assert their economic independence and agency during and after the segregation era.

Developing a new type of art in the process, these 26 artists, including one woman, made careers by depicting the richness and variety of Florida’s landscapes. The group began in the 1950s, but their emotive works still resonate today.

Many of the Highwaymen had felt drawn to art even as children. In the early 1950s, Fort Pierce painter A.E. "Bean" Backus trained Highwayman Alfred Hair to paint landscapes and eventually served as a mentor for others, including Harold Newton. Other future Highwaymen saw the work of Hair and Newton and were inspired to try painting themselves. While considered part of the “Indian River School,” the Highwaymen were not a structured group. The artists, aside from Alfred Hair, were not traditionally trained. They learned techniques from one another, while also developing their own style.

Harold Newton (1934 - 1994), ca. 1968, oil paint on fiberboard, © Harold Newton

Harold Newton (1934 - 1994), ca. 1968, oil paint on fiberboard, © Harold Newton

NMAAHC Collection, Gift of Robert and Flory Kahn in memory of Wolf and Tybe Kahn

Unable to show their work in many of the whites-only galleries in Florida, the Highwaymen relied on a method of high-quantity sales of inexpensive paintings, usually for around $25 each. A technique of “fast painting,” with which the artists produced dozens of works each day provided the group a way to make a living from their art. The method’s quick strokes contributed to the impressionistic nature of the images, while an assembly line system allowed multiple paintings of similar scenes with unique details to be worked on at the same time.

Episode 44: Highwaymen Paintings (A History of Central Florida)

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From the mid-1950s to 1970, the Highwaymen created an estimated 200,000 works and have surpassed that number in the subsequent decades. The artists are recognized for the vibrant and timeless nature of their images. The scenes the Highwaymen depict suggest serenity and undisturbed wilderness. Beaches, marshes, water birds, and poinciana and palm trees are among the most used imagery. The group did not paint landscapes directly, but rather created these scenes from memory and imagination in their backyards, sometimes surrounded by other Highwaymen.

Contrary to the feeling of serenity embodied in the paintings, the works are a product of the Jim Crow era in the South. Accessible employment for African Americans in Florida usually focused on work in citrus groves, tomato fields and factories. The Highwaymen turned to painting as a way to earn a living outside this system of demanding manual labor. The Highwaymen are known both for their artistic style and their enterprising response to oppression, seeking to "make a way out of no way."

Roy McLendon (b. 1932), ca. 1962, oil paint on fiberboard

NMAAHC collection, Gift of Robert and Flory Kahn in memory of Wolf and Tybe Kahn

The variety in sales methods is only one aspect of the Highwaymen’s resourcefulness. The paintings and frames were made from inexpensive construction materials, including fiberboard and crown molding. The artists created and decorated homemade frames as another way to cut down on costs. Deep frames made of repurposed molding allowed the paintings to be stacked on top of each other in cars. This was especially convenient as some works were sold before the thick oil paint had time to dry. These low material costs combined with the short time taken to complete and sell each work allowed the artists to make a profit.

NMAAHC has 18 Highwaymen paintings in its collection. Through their resilience and creativity, the Highwaymen established successful careers on their own terms and their efforts are recognized today.

Browse the Florida Highwaymen Collection

Written by Tess Christiansen, NMAAHC cataloger