Uncovering the Inspiration of Highwaymen Art

Stories Behind the Paintings

The vibrant, sweeping landscapes of Florida, bathed in the glow of sunrise or sunset, are iconic in the world of Highwaymen art. Created by a group of 26 African American artists in the mid-20th century, these paintings captured the untamed beauty of the state and found an audience during a time of segregation. Often sold door-to-door or from the back of cars, the Highwaymen’s work was both a form of artistic expression and a means of survival.

But beyond the bold brushstrokes and vivid colors, there are deeply personal stories rich with struggle, resilience, and inspiration. Let’s dive into some of these fascinating narratives.

A Glimpse into the Swamps: Alfred Hair’s Vision

Alfred Hair is often credited as the pioneer of the Highwaymen movement. His work is known for its bright, lush colors and quick, masterful strokes. As a young man, Hair studied under prominent white landscape artist A.E. Backus, who encouraged him to pursue painting seriously. Hair took this to heart but was driven by more than just artistic passion.

Alfred Hair wanted to make a living from his art, which seemed almost impossible for a Black artist in segregated 1950s Florida. The stories behind his paintings often start with an early morning trek into the wilderness or a moment of reflection along the Indian River. His depictions of swamps, winding rivers, and radiant skies reflected his admiration for Florida’s natural beauty, but also a sense of urgency. Hair was known for painting rapidly, creating scenes full of life, as if he were racing against time. He wasn’t just painting a landscape; he was crafting a path out of the harsh economic conditions many Black Floridians faced.

One of Hair’s family members recalls a story about how he once painted twelve landscapes in a single night, all while his friends gathered around, playing music and laughing. “Alfred was quick, not because he was rushed, but because he saw the picture in his mind before the brush even touched the canvas,” they said.

Harold Newton’s Solitude: The Quiet Inspiration

In contrast to Alfred Hair’s bold personality, Harold Newton was a quiet and contemplative artist. Newton’s paintings, often featuring serene, still waters and solitary palm trees, evoke a sense of calm and tranquility. His inspiration came from spending long hours by himself, observing the way light played across the landscape.

Newton’s family recounts how he would often disappear for hours, driving along Florida’s coastline, absorbing the natural beauty around him. When he returned, he would go to work, capturing the soft hues of dusk or the delicate reflection of moonlight on water. His paintings tell the story of a man who found peace in solitude and used his art to escape the realities of life in a segregated society.

One of his most famous paintings features a single royal poinciana tree in full bloom, set against a vibrant blue sky. His sister once shared that this tree stood near their childhood home, and Newton would sit beneath it for hours, sketching and daydreaming about a future where his art was appreciated by all. Like many of Newton’s works, that painting speaks of hope and beauty in life’s simple moments.

James Gibson: Capturing Florida’s Ever-Changing Skies

James Gibson, one of the most prolific Highwaymen, had a unique love for Florida’s unpredictable weather and ever-changing skies. His inspiration often came from the dramatic thunderstorms that would roll in off the Atlantic coast, turning a clear, sunny day into a wild display of dark clouds and bursts of light.

Gibson once shared an anecdote about how, as a child, he would sit on his porch, mesmerized by the lightning storms. “There was something about the way the sky could go from peaceful to chaotic in minutes that just stuck with me,” he said. His paintings often capture these moments, with clouds rolling in over still waters or light breaking through after a storm.

Gibson’s approach to painting was less about replicating a specific scene and more about evoking an emotion. “I wanted people to feel like they were standing right there, smelling the wet earth and feeling the cool breeze after the rain,” he said. For him, painting was about creating a connection between the viewer and Florida’s wild, untamed spirit.

Mary Ann Carroll: A Woman Among the Men

As the only female Highwayman, Mary Ann Carroll’s story is one of determination and resilience. While she shared the same passion for Florida’s landscapes as her male counterparts, her journey as an artist came with additional challenges. Carroll balanced motherhood and painting, often working late into the night after her children were asleep.

Carroll’s family shares a story about how she sometimes sold her paintings at gas stations or outside diners, receiving far less than they were worth. But she never let this deter her. Her paintings, often featuring bright, colorful skies and flowering trees, reflect her sense of optimism and her belief in a better future.

One of her most famous works depicts a vivid sunset over a palm-lined beach, the sky a brilliant mixture of pink, orange, and red. “That’s what hope looks like,” she once said of the painting. “It’s bright, it’s alive, and it’s always just over the horizon.”

More Than Just Landscapes

The Highwaymen didn’t just paint Florida; they painted hope, resilience, and the promise of a brighter future. Each brushstroke tells a story of struggle, determination, and a deep love for the world around them. Their art is a testament to the power of creativity and the human spirit, rising above adversity to leave behind a legacy that continues to inspire today.

The next time you look at a Highwaymen painting, remember that it’s more than just a beautiful landscape—it’s a story, a piece of history, and a window into the soul of the artist who created it.