While literature and history are two distinct fields, they are not entirely independent of each other. Literature/art and history build off of each other and to fully understand either field, they must be studied in conjunction. The historical setting in which a piece of art is created leaves an indelible mark upon the creation, just as the creation permanently influences history. To examine this relationship, my partner and I decided to study the career of Bob Dylan, a musician who influenced/was influenced by the turbulent atmosphere of the 1960 s. This project took the form of a ten week long Honors Colloquium that my partner and I team taught. By teaching a class rather than writing a research paper, I was able to not only study the interdependence of literature and history, but I was able to experiment with different, interdisciplinary teaching techniques, which themselves helped to illuminate the relationship between these two fields.