The Highwaymen are 26 black artists, a small group of self-taught African-American artists from the area around Fort Pierce, Florida, who got their start selling vivid landscapes — speed-paintings — from their own cars because, in times of segregation in the 50s and 60s, galleries didn't allow them in. Al Black was a salesman extraordinaire, and he offered his services as a salesman on their behalf. In the 1960s and 1970s, the Highwaymen painted tens of thousands of oil paintings sold up and down Florida's East Coast. Black was a bit of a wheeler-dealer and would make more money than the artists would make by hiking the price of the painting and pocketing the difference. Just as things were really taking off, the group's 29-year-old leader, Alfred Hair, was murdered in 1970. Many of the Highwaymen stopped painting altogether, and Black was left without anything to sell. However, he had learned the tricks of the trade from repairing paintings he'd thrown in his trunk and began painting originals himself.
In the 1980s the demand for landscape paintings had dried up and crack cocaine moved across the country, leaving devastation in its path. In Black’s own words, “You can have foot trouble, back trouble, neck trouble, all kind of trouble. You ain't had no trouble until you have crack cocaine trouble.” He eventually worked himself into a habit that cost him $1,000 a day. Al began owing money and paintings to people everywhere. In 1997, Al Black was found guilty of fraud, in connection with a wealthy patroness who befriended Black, and possession of drugs. When asked about his white, elderly patroness, Al says “she loved art and a black man.” He spent ten years in correctional facilities, but when it was discovered that he was a Highwayman, the warden of his prison gave Black permission to paint murals throughout the facilities. He painted hundreds of murals throughout the state penitentiary system, in prison hallways, offices, waiting rooms, dining halls, dorm rooms, and chapels, as other wardens requested his services. By 2007 he was out of jail. Being locked up had been a blessing and Al credits it with saving his life.
The giclée print is on canvas that can be rolled up for portability.
Al Black’s pitch to potential buyers: “ ‘Good morning. Sir, my name is Al Black. I have some oil paintings. I want to know if you all would be interested if it wouldn't take up too much of you all's time.’ And most of the time, they would say yes, I'll look, and once they look, I would sell them something.”
His painting demo begins.
The demo continues. "I can be down and out," he says, "feeling bad that morning. But if I can make it out to where I paint, everything picks up ... and makes me feel real good."
“Carrying them around, paintings would get scarred and I had to fix them. By me being the salesmen, I'm walking around watching the colors that they mix, and I can mix that color, and I would fix them. And so after I learned how to fix some of the stuff, I started to paint myself.” (He learned to paint partly from repairing damaged works that had been loaded into his car while still wet.)
Question: do you paint real scenes or from memory?
Answer: “I been there, I don’t have to go there no more.”
Question: Do you always have water in your paintings?
Answer: “Water sells
Question: How do you know when a painting is finished?
Answer: “When it looks pretty good, I know when to stop.”
Black considers the work finished because it’s been sold to a member of the audience.
Black’s demo painting
The three birds he places in his landscape signifies the Trinity. It is a sure way to identify Al Black’s paintings. On occasion, he will paint a fourth white bird lagging behind. That bird, he said, is him.
The three birds he places in his landscape signifies the Trinity. It is a sure way to identify Al Black’s paintings. On occasion, he will paint a fourth white bird lagging behind. That bird, he said, is him.
The demo painting close-up
Black is a salesman
“Al Black is still a salesman who could snatch you breath away and sell it back to you.” Highway woman artist Mary Ann Carroll describes him this way. “He would sell a mosquito a jacket in the summertime. The only paintings he didn't sell was the ones you didn't give him.”
Black now makes use of modern technology when selling his artwork.
Black’s assistant helps with the sales of his artwork.
Now the paintings are sought after, some fetching prices of between $3,000 and $4,800 each from an online art dealer who sells Florida Highwaymen works.
After the demo, interested audience members gather around Al Black.
“Al Black is still a salesman who could snatch you breath away and sell it back to you.” Highway woman artist Mary Ann Carroll describes him this way. “He would sell a mosquito a jacket in the summertime. The only paintings he didn't sell was the ones you didn't give him.”
Black now makes use of modern technology when selling his artwork.
Black’s assistant helps with the sales of his artwork.
Now the paintings are sought after, some fetching prices of between $3,000 and $4,800 each from an online art dealer who sells Florida Highwaymen works.
After the demo, interested audience members gather around Al Black.
The Highwaymen works of art on display
The works are classified as “Outsider Art,” or "Folk Art. They honed techniques to rapidly produce their paintings and developed strategies to sell and market their artwork outside of the formal world of art galleries and exhibitions .
The Highwaymen were rediscovered in the mid-1990s and today are recognized as an important part of Florida culture and history. Al Black, and the other 25 artists known as The Highwaymen (18 of whom are still alive), were inducted into the Florida Artists Hall of Fame in 2004. Black is back in Fort Pierce, painting in the old Highwaymen style: outdoors, several canvasses at a time. He paints traditional Highwaymen subject matter: rivers, beaches, waves, sunsets, and varying kinds of foliage. And how does he know when a painting is finished? In his own words, “A painting isn’t finished until it’s sold.“ Now people come to him to buy artworks and he sells with the same smooth talking finesse and enthusiasm that he has always used. Al is proud to report that he has been drug free since his early days in prison.
It has been said about Al Black: “His ability to charm a prospective customer or journalist, even while you know you may be hearing exaggerations (or maybe lies), is what marks his personality.” In his presentation at the Alliance, Al told his life story truthfully, without glossing over the demeaning parts, but he’s a storyteller and there’s something about his manner of speaking that draws in his audience completely, and we in the audience at the Alliance that morning were no exception.
