This study describes three aspects of the learning context of a Community-Based Theatre Arts Program with attention to their impact on the literacy practices of adolescent participants. Studied were 1) talk about social and political difference between staff and youth participants, 2) participants' perception and uses of space for program purposes, and 3) community-building activities. Also, this study describes those contextual factors as they support or constrain the establishment and development of expert-apprentice relationships between adult mentor artists and youth participants. A second phase of the study involved following four participants back to their home school language arts classrooms. The same three aspects were observed there, and data from these observations were compared to the data from the program. The study concluded that the youth participants were more engaged and involved in the program activities compared to the literacy activities in their language arts classrooms. Key differences between the two contexts were 1) apprentice-type relationship to adult discourse, and 2) spatial practices. Expert adults in the program modeled compelling identity positions.