This nontraditional dissertation, which I prefer to label as a manuscript, is a qualitative study that explores the complexities of life in the South Bronx. This manuscript represents my multifaceted journey as a young Puerto Rican man making meaning of life in the South Bronx as well as making meaning of my lived experiences navigating through academia. This journey implicitly employs a theoretical framework of détournement, critical race theory, lived experience, and representation in order to construct a counterstory that critiques popular and distorted (stereotypical) representations of life in the South Bronx. Additionally, this manuscript examines the complexities in the representations of Hiphop. Along this journey I explored the life of world renowned Hiphop pioneer, Phase 2. Phase 2’s experiences and knowledge concerning interpretations of the origins, shifts, and objectifying of Hiphop speak to its [Hiphop’s] social origins, evolution, and position in reality. The lived experiences of Phase 2 are mirrored against my own lived experiences in order to create a dialogue that speaks to Hiphop as culturally lived experiences rather than a set of elements (rapping, break dancing, aerosol art, and dee jaying) to which Hiphop is often reduced.