One of the most memorable characters of the play, Wining Boy is a wandering, washed-up recording star who drifts in and out of his brother Doaker's household whenever he finds himself broke. A comic figure, he functions as one of the play's primary storytellers, recounting anecdotes from his travels, glory days, and the family history. He is one of the two older players in Wilson's scenes of male camaraderie, playing a sort of godfather to Lymon when he deftly sells him "magic suit" with the promise that it will assist him in the arts of seduction. Finally, Wining Boy also appears as the other character in the play who can speak to the dead, conversing with the Ghosts of Yellow Dog and calling to his dead wife, Cleotha. As with Berniece, his musical abilities apparently put him in closer communication with the deceased, the call and response of the play's many songs oftentimes a call across the grave as well.