In this article, the author examines the dilemmas that emerged in his role as teacher-researcher in Hip-Hop Lit, a hip-hop-centered literature class within an evening education program. Specifically, the author examines the complex and often competing roles and identities that he performed within the research context, as well as during the process of ethnographic writing. The author details how these roles and identities were mediated by the various allegiances, commitments, and beliefs that prompted the study, as well as those that developed in response to the relationships that were forged with research participants. The article argues for a constant reflection on and response to issues of identity, authority, and power while in the field and "behind the desk."