In this paper, the authors consider early results from their ethnographic research in urban drama classrooms by parsing the aesthetic and social imperatives at play in the classroom. Moved by the observation that teachers and students alike seem to be pursuing elusive aesthetic and social ideals, the authors draw on Judith Butler's notion of "melancholia" to explain the feeling of disappointment that sometimes follows difficult drama work--the sense, as a teacher in one of the research sites put it, that "it could have been so much better". Reflecting on a larger international research project, "Urban School Performances: The interplay, through live and digital drama, of local-global knowledge about student engagement" (USP) project, the authors illustrate and theorise this concept of disappointment using qualitative data from two urban Toronto drama classrooms. On the surface, one of these sites was focused on aesthetics and the other on social development, but the authors dig deeper to consider the subtler values and outcomes that are made available by ethnographic research. This partly leads to a consideration of how students, teachers and researchers alike are each burdened with a responsibility to "perform" and "advocate". (Contains 4 notes.)