This chapter explores the role that cartoon minstrels played in the transition to sound in American commercial cinema. As a part of live extravaganzas staged with silent films in the 1920s or in the sing-along cartoons of the Fleischer studios, animation formed a bridge between the worlds of the screen, the stage, and the audience. Just as live minstrels such as Al Jolson and Eddie Cantor were important in cinema’s transition to sound, so were animated minstrels. Playing on animation’s tradition of questioning and reestablishing the boundary between the screen and the real world, cartoons trained audiences in how to understand their changing relationship to a new screen space. Cartoons became replacements for the live shows that had formerly framed silent features. As artifacts they offer insight into the complex relationships between race and the organization of social and cultural space, and of the labor that makes and occupies that space.