Michael Ray Charles is filmed on location at his home and studio in Austin, Texas. Through his studies of advertising, the minstrel tradition, and blackface, Charles seeks to deconstruct and subvert images of blackness through painting. "I've been called a sellout. People question my blackness. A lot of people accuse me of perpetuating a stereotype," he says. "I think there's a fine line between perpetuating something and questioning something. And I like to get as close to it as possible." Pointing out items from his collection of memorabilia, Charles traces the transformation of stereotypes in his work. The segment concludes at an exhibition of Charles' work in New York City.