This dissertation demonstrates how theatrical performances allowed for African political interventions into many of the most significant political moments in Kenya’s colonial history. Though the African majority was largely blocked from participation in the white settler colony’s centralized political institutions, many Africans found roles as musicians, audience members, and even actors within their colonizers’ ubiquitous pastime of amateur theater. By refashioning themselves as performers, disenfranchised people of color reinvented themselves as political actors—arming themselves with the language and ideology of the imperial state and using that language to both participate in and to undermined colonial politics. Bringing expressive culture to bear on Kenyan history, suggests that East African political culture has a dual nature that complicates narratives of collaboration or resistance. The great body of studies published on Kenyan colonial history to this point have given us a rich understanding of both ethno-historical forces and the frameworks of major political tensions. Because Kenya was a deeply divided colony, one in which both African and British ethnic nationalisms demanded central roles, it is easy to be drawn into a fragmented understanding based on historically entrenched cultural difference. The study of theater in this period gives us a more integrated and accurate way to understand the period’s many dynamics, because it shows that Africans, through their expressive culture, all the while moved back and forth across constructed cultural boundaries. They took repressive elements in the colonial armory and undermined them. They played scenes against the apparent grain to find ways for strong political and social self-expression. To reconstruct Kenyan theater as a regional practice, in addition to pursuing official colonial papers and archives in Nairobi, London, and Oxford, I also conducted two years of fieldwork in Kenya. What distinguishes my method of research, is the inclusion of photographs, films, theatrical programs, musical scores, and scripts—archival materials that historians rarely consider. These sources make clear that colonial-era actors were neither sellouts nor transgressors, but cultural interpreters who understood their fast-moving, divisive worlds and used the stage as a middle ground and a mediating voice.