James joins Daniel Emmett's minstrel troupe as it marches down the town's main street, a grotesque procession of white performers in blackface, Norman passing as white while painted black, and James painted in a way that makes his real identity even more precarious. As white townspeople cheer, clap, and laugh, James sees that they are enjoying a shared act of ridicule aimed at Black people and enslaved people. The parade and songs make the town itself seem unreal to him, and he concludes that the line between the so-called free side and slave side means little in such a place.

At the town hall auditorium, the troupe performs more songs, and James quickly keeps up well enough to sing the choruses. The audience responds with delight, taking pleasure in the caricature being played before them. James endures the humiliation by reminding himself that he is, in one sense, fooling them, even as their laughter makes the performance emotionally painful.

After the show, the white performers can safely blend into the crowd, but James cannot leave without help and is left stranded when Norman is occupied. A young white woman named Polly approaches James and flirts with him, asking his name and where he has traveled. Terrified, James gives short answers and even tries to discourage her by saying he has a wife. The encounter becomes more dangerous when Polly's father arrives, inspects James's face and hair, and boasts that he can always detect a Black person or an enslaved person by smell. Emmett intervenes just in time, pretending James's hair is part of an expensive wig and steering suspicion away.

Once outside, James and Norman admit how frightened they were, and James says plainly that he must get away because he cannot survive indefinitely under makeup and disguise. Emmett jokes about how badly things might have gone if James had been exposed, but Norman points out that all of them would have been at risk, which silences Emmett. Walking back to camp, James reflects on what the encounter awakened in him: anxiety, anger, and a more complicated judgment of Emmett. Though Emmett claims not to believe in owning slaves, James recognizes that buying him for a purpose still makes Emmett part of the same system, and James leaves the chapter more determined to escape.