This case seeks to add to the growing research on the hip-hop culture and the importance of visual images in qualitative research. This study explores the use of visual imagery as a tool for describing the changes that have led to hip-hop culture's transformation to the hip-hop industry while also providing an interpretation of the impact of hip-hop-influenced visual imagery on two educators. Participants selected a text, film or video, book or image that spelled out the journey that the participants traveled within hip-hop from its inception to today. The use of imagery, incorporated into in-depth interviews, extended the dialog with participants, and evoked deeper comments about their backgrounds, pedagogy and the connection to hip-hop. The participants are educators who are knowledgeable about hip-hop culture from a multi-decade perspective and view themselves as lifelong members of the hip-hop community.