Perhaps as well known for his colorful, and at times troubled, life story as he is for his paintings, Al Black is a unique character in the cast of the 26 Florida Highwaymen painters.
Born in 1947 near Jackson, Miss., stories of Black’s life until his early 20s are devoid of any hint that life as an artist awaited him. In his teens he labored as a fieldworker picking vegetables and fruit, later graduating to various roles as a driver. When he eventually landed in Fort Pierce in the early 60s, he took a job cleaning and moving typewriters for the Fort Pierce Typewriter Company and, always a great talker, he soon convinced the company to take him on as a salesman. It was during these early years in Fort Pierce that Black met Alfred Hair, and his path finally intersected with the Highwaymen.
Hair, himself an artist and rising entrepreneur, recognized the value Black’s skill as a salesman would bring to his efforts to produce art works with Harold Newton and others and sell them, essentially, door-to-door to businesses and motorists along the highways. He hired Black as one of the group’s first salesmen in 1964. “I was the salesman for the group when it first started,” Black told the podcast Highwaymen Paintings (A History of Central Florida). “I went all up and down the highways selling paintings. If I had 30 paintings that day, I would sell 30 paintings that day. We couldn’t sell our paintings in galleries at all, we’d have to sell them out of the trunk of our car, up and down the highways, and motels, and doctors’ offices.”
A gifted representative for the group, Black told The Highwaymen Trail, a heritage trail organization run by the city of Fort Pierce and the Florida Humanities Council, that he had a system, a script, for approaching would-be buyers on his routes. “Good morning, my name is Al Black,” he remembered telling those he would approach. “I’m representing the Alfred Hair artists. I’d like to know if I can take up some of your time.”
“He could sell a jacket to a mosquito in summer,” his contemporary and fellow Highwaymen painter Pastor Mary Ann Carroll told NPR in a 2012 interview.
It was as a salesman for the group of artists now known as the Florida Highwaymen that Black began learning their techniques, first out of necessity, and later out of a desire to paint himself. As a salesman, he quickly realized that the paintings he would take out onto the road with him were often still wet and easily damaged by the time they reached a potential customer.
“So, carrying them around, they would get messed up,” Black told NPR, “The paintings would get scarred, and I had to fix them. And after I learned how to mix everybody’s colors – because by me being the salesman, I’m walking around watching the colors that they’d mix, and I could mix that color and I would fix them. And so, after I learned how to fix them and stuff, I started to paint them myself.” After first assisting other painters with completing their paintings – filling in a sky here, the water there – Black soon began creating his own work and selling his paintings alongside those of the rest of the group.
After Hair’s death in 1970 and a decline in the market for Highwaymen paintings, the 80s brought years of tumult and turmoil for Black, as he developed both a crack cocaine addiction as well as a penchant for making money through various dishonest and illegal schemes. Both habits landed him in and out of jail until 1997, when he was sentenced to 12 years in a state prison for cocaine and fraud convictions.
Today, Black credits prison with saving his life. It was in prison that he kicked his cocaine addiction for good, and rediscovered his gifts as an artist. He began painting murals as well as canvases he would sell in the prison crafts shop, estimating that by the time of his early release from prison in 2006, he had completed more than 100 murals at institutions within the Florida state prison system, and hundreds of individual canvases.