Sylvester Wells

Highwaymen Artist

Sylvester Wells

The fifth of ten children, Sylvester Wells was born in Jacksonville, Fla. in 1938. His father, a truck driver, and mother, a homemaker, were devoutly religious and instilled in their son the importance of faith before all other pursuits and it is a lesson that has stayed with Wells throughout his life.  

Interested in art from a young age, Wells was primarily interested in sketching and drawing in his younger years but there is little information about how much work he did as an artist as a teenager. After graduating from high school around 1956, Wells spent a few years overseas with the Army, and then returned home to settle in Cocoa, Fla., with his wife Consuela.

Unusual for a Florida Highwaymen painter, Sylvester Wells says he has never been to Fort Pierce, Fla. It wasn’t until he was 25 that he first encountered one of the painters now associated with the group hauling paintings from his car to sell at the local bank in Cocoa. It was Alfred Hair, considered the founding father of the Fort Pierce group of Highwaymen (painter Harold Newton worked in a similar fashion and another group of painters grew up around him in Gifford, Fla.), and Hair was happy to talk to Wells about his artwork and how he sold it.

Wells had already developed his talents as a portrait and sign painter in Cocoa so, convinced he could make a living making and selling landscapes as Hair did, Wells immediately set out to give it a try himself. “His first try at a landscape turned out looking like a three-year-old had painted it and he nearly cried in defeat,” The Highwaymen Trail, a heritage trail organization run by the city of Fort Pierce and the Florida Humanities Councilreports.

Knowing he need some guidance, Sylvester Wells set out to find Harold Newton, who he’d heard was painting in Cocoa at the time. Newton and his brother Sam were happy to assist, and Wells began spending his days with the brothers as they painted, learning their techniques, and then going home and practicing at night. “I just stood and watched,” he told The Highwaymen Trail. He purchased the materials Harold and Sam recommended he use and spent hours and hours perfecting his work. “I practiced and practiced and practiced. Soon, I could paint anything Sam could paint, and people started buying.”

Wells sold his work door to door and from his car along the highways as the other Highwaymen did and made an excellent living at it for more than 40 years. Representative of the most iconic of Highwaymen scenes, Wells’ early work focused on Floridian sunsets, waving palms, colorful skies, and crashing ocean scenes. But he did later begin depicting scenes of everyday life happening within his landscapes. Cracker Cabin, his painting of a “Cracker-style” cabin set within a lush scene of Florida’s interior, is one example of this work, and is now part of the permanent collection of the Smithsonian Museum of African American History and Culture. 

Inducted into the Florida Artists Hall of Fame in 2004, Sylvester Wells lived in Tennessee until his death in 2023, devoting most of his time to Bible study and ministry after losing his sight to glaucoma. In addition to the Smithsonian, his work hangs in galleries and collections around the country.

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