In this article I will explore the concept of transgression within the realm of rock music using the biography of Lou Reed, known for such songs as ‘Walk on the Wild Side’ and ’I’m Waiting for the Man’. I discuss Lou Reed’s social transgressions as a reaction to and resistance toward institutions of social control such as family, media and the music industry, which stigmatized him as an outsider. This study, which is based on secondary material, such as biographies, interviews and songs, shows how Lou Reed transgressed social norms with respect to drugs, sex, and gender.