This article explores the possibilities for effecting Transformative Learning in students of German language and culture through the use of popular music videos, in both the target and the students’ own languages. Transformative Learning, a term that has differing valences in numerous academic disciplines, is employed here in its social-scientific context to denote the ability of learners to negotiate successfully between different cultural frames of reference in order to understand their experiences of cultural dissonance (Anderson & Cunningham, 2010). While Transformative Learning is indeed a higher order cognitive goal, the author argues here that the German language classroom can be an ideal location for building the skills (reflection, interpretation, acquisition of concepts and nuanced self understanding) that set the stage for Transformative Learning to take place over time. The author first lays the theoretical groundwork for this type of learning, followed by a brief introduction to the concept of transculturation (Pratt, 2005) as an important framework for understanding developments in German hip-hop musical and visual styles from the early 1990s to the present. The article includes an in-depth comparison of music videos from Germany and the United States.