The pervasiveness of popular music and its associated practices in current youth cultures brings into question the relevance and effectiveness of more traditional music pedagogies, and propels a search for a more current and engaging music pedagogy informed by popular music practices. With this as the basis, this study seeks to explore factors that may enable the success and effectiveness of popular music programmes in public schools through the lenses of three Singapore secondary school teachers as they conducted their popular music lessons over seven to ten weeks. In the process, the study also describes how these teachers pragmatically negotiated the execution of these programmes within Singapore's unique educational context. The findings may serve to inform music teachers and school leaders keen to establish similar programmes as a matter of on-going dialogue.