The Highwaymen Today

The Highwaymen have left their mark on the world. The original painters are aging, some of them have passed away. Those who are able, continue to paint with vigor and pride. It’s still about making a living, but it’s also about identity and a connection to a particular time and place. It’s as if painting defines the Highwaymen — both as a group and as individuals. They are more themselves when they create a landscape. For them, it’s about being good at something, while being recognized and valued.

The Highwaymen’s work, and perhaps some of their legacy artists, will certainly be collected and written about for years to come. Their paintings, now in major collections around the world and increasingly in museums, help define the history of Florida’s landscape and the history of art.

For those lucky enough to have an early work, Florida’s brilliant skies and inviting waterways may elicit sublime ideas about nature (and perhaps God). It may suggest a landscape that is now vanishing. A Highwayman landscape may also cause you to think about the artist and his or her particular experience in the history of Florida and art.

Poet and playwright Amiri Baraka, founder of the Black Arts Movement, understood that culture and social change could work together. The Highwaymen created tens of thousands of striking landscape paintings that define the way Florida used to look, but they did more than that. They created a life for themselves, through painting, as they struggled to break free from the confines of the Jim Crow era. Their determination to create artworks good enough to be purchased and hung on a wall, from Baraka’s perspective, could be seen as an activist act, no less important than the civil rights work of those brave black men and women who stationed themselves at a Woolworth’s counter and asked to be served. They quietly and respectfully brought with them tangible items, inexpensive works of art that moved into white homes, hotels, and businesses. These paintings said something about spaces that belonged to everyone. While the spaces they moved into are now far more open to them, the landscapes they depicted are increasingly rare.

The Highwaymen will be remembered for their grit and determination. They are role models for all of us, not as perfect human beings, but individuals who struggled, sometimes failed, but ultimately transcended their designated roles through artwork. Knowing their stories is to know them as creators of their worlds, undeterred by circumstances of poverty and race. Remembering them is to gain insight into what community once meant to black people, in spite of the fact that their community was horribly restricted by outside forces. Remembering them is to know our history and how the slightest act of resistance to oppression can be powerful.

With renewed imagination and determination, the future of the Highwaymen will be tied to the future of the Fort Pierce African American community and African American communities across the country. As the artist/hustler Theaster Gates, working on the South Side of Chicago suggests, acknowledging African Americans’ rich culture can lift the burdens of slavery, Jim Crow, and racism.

Today, the Highwaymen are well known for their dazzling landscapes and their skill at selling them on the roadways during Jim Crow times. That might be enough, but their stories are more than that. They are about vivid worlds and vivid lives. Put together, the Highwaymen story is about working the fields, (mostly) male camaraderie, Florida’s roadways before the interstate, salesmanship, and desire. It’s about the experience of living in Florida’s heat and humidity without air-conditioning, sharing beers, counting money, and dreaming about a better future. It is also about Joe Frazier, Jim Crow, the Civil Rights Movement, the railroad tracks, and blacktowns and whitetowns across the South. It’s about one white artist who opened up his home and studio to countless dreamers from all walks of life when this kind of thing just wasn’t done. And it’s about a kind of rhythm that comes from Motown, the blues, jazz, gospel, and the sounds of nature. The Highwaymen’s future, in some ways, is about our collective past and our collective future. For these men and one woman, and all those who have learned from them, the future is about understanding the potential of choosing a poetic place in the world.

We know that cultural legacies are important. They help us make sense of our lives. The Highwaymen created a place for themselves that was better than the one they might have lived. In so doing, they have enriched all of our lives and shown us the way.