This study employs interactional sociolinguistics to address the role of principalship in fictionalized improvised entertainment. Although improvisation offers a singular forum for approaching awkward cultural issues like racism, improvisers may evade this exactly seeing principalship ambiguity. This study adds to contemporary work in sociolinguistics addressing the intricate manners in which language may be employed in interaction to express cultural meaning. We explore how improvised contexts can offer an ambiguity of principalship. The animator could in fact be the principal, offering the performer the potential to articulate cultural truths. The possibility that he/she may not be provides a freedom from responsibility for what is being said, a space that performers may exploit to animate controversial beliefs without the normal interactional repercussions. We explore this in two sets of data, one from a production day of a Canadian television series in which the dialogue is improvised, and one from a large-scale ethnography of a community in Washington, DC, of performers of improv (a humorous theatrical performance in which characters, dialogue, and the performance structure itself are improvised). Observing footing shifts and drawing on metacommentary, we consider how improvisers show awareness of this potential, and we consider the cultural implications. Thus, while improvisation provides a unique forum for tackling difficult cultural issues, such as racism, improvisers may avoid doing so precisely because of the ambiguity of principalship. This research contributes to the current work in sociolinguistics considering the complex ways that language may be used in interaction to articulate cultural meaning.