Though often posed in oppositional terms, modernist and popular music have always shared common ground. This is reflected in a growing body of literature that examines crossover as much as conflict, but mutual entanglement has been the case from the get-go. It is of course important to understand modernism and pop as two fairly distinct forms, but the territory between them has proved fertile. This chapter studies that territory. It provides a critical synthesis of literature on the topic, and looks at a number of concrete musical examples of ‘popular modernism’, a limit case of pop/modernist entanglement.