Left: Untitled, 1993.
Right: Beware, 1994. The old stereotypes have only been repackaged, Charles says.

Right: Clockwise from top left, four paintings from the Liberty Bros. Permanent Daily Circus series: Blue Period, 1995, Oop’s, 1995, Desperados Leap for Life, 1996, and Smiles, 1996. “I’m trying to be as honest as possible in depicting these caricatures,” says Charles. “Sports and entertainment were avenues in which blacks were allowed to excel. This is American history. This is American culture.”

Clockwise from top left: Vote Black, 1993, For Women, from the Forever Free series, 1992, and Invest Well, 1996, reflect Charles’s belief that the promises of freedom—and the free market—have often seduced and abandoned African Americans. “We don’t really talk about the things we need to talk about,” he says. “These stereotypes are images that haven’t really been addressed in our society.”

Right: A Lincoln penny glued to his paintings is Charles’s trademark. Photograph by Patrick Demarchelier