This article describes a collaborative and emergent approach utilizing Tupac Shakur's "Brenda's Got a Baby" to leverage theory education. This song/video uses a fictionalized account of a pregnant 12-year-old African American girl to chronicle the ecological realities of life in the inner city (e.g., teen pregnancy, drug addiction and trafficking, incest, poverty, dysfunctional families, lack of opportunity, ineffective educational and welfare systems, runaway youth, commercial sexual exploitation, violence, and a racially insensitive law enforcement response). Because of the complexity and convergence of multiple issues and social problems in Brenda's life, and their impact across the micro-macro spectrum, this song/video is an effective anchor for a semester-long emphasis on a critically conscious approach to theory. This article (a) reviews hip-hop as a vehicle for pedagogy; (b) explores Tupac's early history and approach to information dissemination; and (c) discusses underlying assumptions and application in BSW-, MSW-, and PhD-level theory courses.