Carnival performances and their political implications underwent significant transformations in nineteenth- and twentieth-century Guinea-Bissau, West Africa. By focusing on two periods of colonization, this article examines carnival as an event that involves a multitude of meanings and forms of imitation that could imply resistance to colonialism, but were by no means limited to critique and upheaval. Colonizers, colonized, and the people mediating and situated between these overarching categories could ascribe various meanings to specific performances, thereby underlining the multi-dimensional character of carnivalesque rituals and their heterogeneous significations. In these performances, mimicking the colonizers was an active, creative, and ambiguous undertaking that repeatedly and increasingly challenged colonial representation. However, the colonial state proved to be far less controlling and totalizing than is often assumed.