Drawing on research with musicians, producers, critics, business figures, copyright specialists, and young audiences, the author analyzes popular music in contemporary Bulgaria and argues that the local music scene is characterized by the ideas of amorphousness, fluidity, and marginalization, rather than clearly defined structures. She shows how contemporary Bulgarian popular music has local specificities but operates through the tools of a global dialogical platform, in which folklore references and language are markers of identity, as well as involving a negative stereotype of the Other. She emphasizes the idea of the crossroads in how the music interacts with social, political, and economic change; the complexities of incorporating global and local markers of meaning; and the relationships between cultural concepts of centrality and peripherality. She uses the idea to explore levels of change and struggle in popular music and focuses on the contemporary cultural and structural characteristics of the environments in which popular music operates and how they have evolved under the influence of democratic transitions following the communist regime. She discusses key areas of debate and concepts in popular music research; her research design and processes of fieldwork data collection, analysis, and interpretation; the characteristics of the local pop music sector in Bulgaria, the cultural influences of post-communist transitions, and the cultural context of the crossroads, where global and local identities interact; and the fluid character of the local music sector, the power relations that define its dynamics, the impact of post-communist transitions on music meanings, and the complexities derived from Bulgaria's position between the cultural constructs of the East and West.