This article explores how and to what extent collaborative ethnographic fieldwork enables comparison both inherently and in practical terms. More often than not, ethnographic comparison involves the juxtaposition of studies carried out separately by individuals and relates to comparing arguments rather than empirical incidents. This obscures important contextual specificities across research sites and dilutes the comparative endeavor. We argue that it is necessary to be transparent about the way empirical data are produced for meaningful comparative analysis to be generated. One promising way to ensure this is through a reciprocal engagement with each other’s field sites by means of joint fieldwork. This form of collaboration iteratively produces a combination of empirical experiences of bafflement on the one hand and forces the dialogical integration of different epistemological perspectives on the other, which we label “epistemo-methodological disjunctures.” Drawing empirically on our collaborative ethnographic research on gang dynamics in Nicaragua and South Africa, we describe how questions surrounding the nature of the object being studied, the practicalities of collaborative comparative ethnography including the importance of understanding each other’s “ethnographic ground zero,” and the need to reconcile epistemological differences all emerged as critical to shaping the possibilities of comparison.