Tom Petty (1950-2017) was an award-winning American musician and lyricist long associated with cannabis and other drugs. This lesson revolves around Tom Petty’s song You Don’t Know How it Feels (1994), which provides a rich opportunity to build drug literacy while exploring the connections between experiences, relationships, emotions, thoughts and actions. The song, with its reference to rolling a joint and sharing it with friends, sparked controversy at the time. This provides an opportunity to explore issues like censorship and artistic freedom. And the history of Tom Petty and his long-time band, the Heartbreakers, provides further opportunity to explore the impacts drug use can have on life, work and relationships. In each case, the use of dialogue rather than the transmission of the “right message” is likely to lead to greater understanding. The instructional strategies provided are examples of how this could be achieved.