With the growing number of entertainment—education (E—E) interventions worldwide, and the extensive evaluation research on their impacts, the time is ripe to explore in—depth the theoretical underpinnings of entertainment—education. This introductory article provides a historical background to this special issue of Communication Theory on entertainment—education, and charts a 5—pronged theoretical agenda for future research on entertainment—education. Theoretical investigations of entertainment—education should pay greater attention to the tremendous variability among entertainment—education interventions and to the various resistances to entertainment—education interventions. E—E theorizing will also benefit from close investigations of the rhetorical, play, and affective aspects of E—E. Further, E—E “effects” research should consider employing a broader understanding of individual, group, and social—level changes and be more receptive to methodological pluralism and measurement ingenuity.