Floridians Check Your Storage for Art-‘Highwaymen’ Paintings Are Worth Thousands

Native Floridians, you may want to look through your storage. There’s a decent chance you have a painting by one of the Highwaymen artists amongst your forgotten things. If so, you may own a piece of art history that is now highly collectible and possibly worth thousands of dollars.  

Highwaymen paintings have a distinct style. This painting is a classic subject, typical of the look. This painting currently hangs in Governor’s mansion.

The Highwaymen artists started in the 1950s and 1960s as a self-taught collective of mostly Black artists led by Alfred Hair and Harold Newton. The group was not formally organized but was a loose affiliation of artists who painted and sold their artwork by traveling the highways and selling their paintings door-to-door. They often worked from memory or photographs, creating quickly executed and highly stylized images that capture Florida’s natural landscapes’ unique beauty and character. The Highwaymen artists became known for their distinctive style, bold colors, dramatic brushwork, and a sense of motion and energy in their depictions of Florida’s scenery. They could sell their paintings to tourists, motels, and businesses, often for just a few dollars each.

Vibrant Highwaymen painting depicting a night seen. This painting can be found in an office at the Florida Capitol.

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The Highwaymen artists were a significant part of Florida’s art history and cultural heritage, particularly during the mid-20th century. Their art is highly collectible and can be seen in museums and galleries. Florida’s First Lady Casey DeSantis has taken an interest in the artists, and many Highwaymen paintings are currently displayed in the Governor’s Mansion in Tallahassee.

Highwaymen painting at the Governor’s mansion in Tallahassee.

Despite facing racism and discrimination, the Highwaymen artists were able to develop successful careers and achieve recognition for their work. Some of the most well-known Highwaymen artists include Alfred Hair, Harold Newton, Mary Ann Carroll, Al Black, Sam Newton, Robert Butler, and Livingston Roberts. Each of these artists contributed to the development of the Highwaymen style.

This Highwaymen painting is in its original frame, adding to the value.

Some of the Highwaymen artists are still alive today. As the group needed to be formally organized, it took time to determine how many Highwaymen artists there were. Still, it is estimated that there were approximately 26 active members during the peak of their popularity in the 1960s and 1970s.

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Casey DeSantis, the current First Lady of Florida, has shown a strong interest in the Highwaymen artists and the paintings. In 2019, she announced the launch of the “Resilience and the Last Coast” initiative. As part of this initiative, the First Lady worked with the Florida Department of State to organize a Highwaymen art exhibit at the Historic Capitol Museum in Tallahassee. The show featured over 30 paintings by various Highwaymen artists, including several from the Governor’s Mansion collection.

This Highwaymen painting is a bit unusual because of the black, white, and gray color scheme.

Although the Highwaymen were primarily a group of male African American artists, there were also a few female artists associated with the movement.

One of the most well-known female Highwaymen artists is Mary Ann Carroll, born in 1940 in Florida. She grew up in poverty and began painting in the 1960s after meeting fellow artist Harold Newton.

Some Highwaymen artists still paint today; throughout Florida, you can meet a new generation of artists who continue to paint in this style. If you’re looking for original paintings, they can still be found in antique stores and galleries for a price.

If you visit the Capitol in Florida, some legislators have Highwaymen art in their offices. Highwaymen and their paintings are a unique part of Florida history, sure to inspire all for many years.

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