Based on the experience of teaching the history of American hip hop music to a classroom of Canadian university students, the author considers the disjuncture between the cultural orientations of herself and her students. The author considers teaching methods to solve the place-based disjuncture that often occurs when teaching genres such as hip hop, as well as in the teaching of mediated and virtual musics. She draws upon the fields of ethnomusicology and popular music to consider solutions that examine the relationships between the performers and listeners of hip hop music and the mediators that are involved in the process of negotiating the space that is created in the production and consumption of music and who have the greatest influence on how the music is heard by the listeners. This article presents several ideas on how cultural specificity can be dealt with when studying or teaching about a musical system.