Since the Highwaymen aspired to sell their paintings as quickly as they were made, Al Black took the still wet paintings on the road, and he learned to paint by repairing smears and scratches that occurred as he loaded and unloaded the paintings from his car throughout the day. He often asked the artists not to sign their paintings, explaining that by offering to sign a painting in front of a consumer would facilitate sales; he would sign his own name to these paintings. Black did not start creating his own works until Alfred Hair’s death in 1970. Until then, he simply could not spare the time to paint. He was earning huge profits as a salesman, taking a commission of 30 percent for each painting he sold and selling at breakneck speed.
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While incarcerated Al Black was permitted to paint. He created 90 murals at the Central Florida Reception Center, a clearinghouse prison east of Orlando.