Willie then asks Wining Boy to play the piano. Wining Boy moans that he is tired of carrying a piano on his back. "Am I me? Or am I the piano player?" he asks. Willie remarks that someone better play the piano quick, rehearsing his plans to sell it and claim Sutter's land. Once again Doaker insists that Berniece will not sell it and begins to explain its history to Lymon.
Scene 2 focuses on male camaraderie, the first of two in the play, introduces the ironically named Wining Boy, a wandering, washed-up musician who is clearly past his time and looks back upon his life with an "odd mixture of zest and sorrow." A traveling man, he functions as one of the play's primary storytellers, delivering in this scene a number of thematically significant speeches. Certainly his call to the Ghosts of the Yellow Dog, a dialogue with the dead at the crossroads, once again underlines how the play poses these characters' ancestors as sources of strength and renewal. Wining Boy is not only occupied with the ghosts of the railway, however, lamenting the passing of his wife and the certain home she emblematized. As the omnipresence of these ghosts suggest, The Piano Lesson is a play about mourning and attending to the memory of those lost. As in Wining Boy's stories of the crossroads and Cleotha, this mourning will specifically involve the address across the grave, a call to the dead both in speech and, importantly, in music.
Though not named explicitly, among the ghosts with whom the men are in such dialogue are those of slavery, ghosts that assert themselves in the group's memories of the Parchman Prison Farm. As Wilson largely leaves this reference unexplained in the script, Parchman requires a brief historical detour. The Parchman Prison Farm opened in 1904 by Governor James K. "White Chief" Vardaman as a highly profitable labor camp. Boasting over 20,000 acres and covering over forty-six square miles, the prison contained a sawmill, a brickyard, a slaughterhouse, a vegetable canning plant and two cotton gins. Unlike most prisons that consumed state revenue, Parchman furnished the state treasury annually with substantial profits from the sale of cotton and cottonseed.
Prisoners at Parchman endured conditions and cruelty that paralleled the former days of slavery. Inmates lived in over-crowded cells with bloodstained floors, overflowing waste buckets, and vermin-covered walls. Convicts were forced to work long hours in scorching cotton fields and were barbarously whipped by "Black Annie," a three-foot long, six-inch wide leather strap. Convicts were always stripped to the waist, and whipped in front of other men. An apprehended escapee faced an unlimited number of lashings. Prisoners were supervised by a handful of paid guards and a large number of armed prisoners called "trusty shooters" with the authority to shoot escaping convicts.
The men's shared history at Parchman—a history shared across generations—and encounters with a racist legal system, marks the specter of slavery in their lives. In particular, Lymon's anecdote of fleeing Stovall after his racist arrest and sale into bondage can only evoke the memory of the runaway slave. Also connected to these memories of Parchman is Wining Boy's allegory of the difference between the white and black man, a difference that lies in the white man's ability to use the law. Notably, Boy Willie rebels against the fact of these racist conditions, declaring that there is no difference between him and the white man, and that he can only follow laws he considers just. This rebellion against racism prefigures his final outburst in Scene 5.