This article focuses on the dialogues within and between Disney's The Princess and The Frog and a 1930s animated series about a young Black boy-Little Ol' Bosko. Both films feature Black characters who navigate a fairy tale world set in the swamps of southern Jim Crow era America in which they grapple with fears about reductive and demeaning black film stereotypes. Although they are in some ways trapped within the white gaze of the film's meaning, I argue that in their fantasies, both Bosko and Tiana outmaneuver the regime of representation that underlies racial stereotyping, opening a space for trans-coding and revision of its meanings. In addition, a comparison of the films demonstrates a clear improvement from the 1930s in terms of an increased differentiation in the representation of Black Americans, acknowledging, if not embodying, the fact that "Black America" is a diverse and complex reality.