Popes’ relationship with modern media can be assumed as a prism through which the cultural, social, and political transformations of the twentieth-century papacy can be observed. Cinema, radio, and television were means through which the voice and the image of the popes were almost known simultaneously for the first time in history throughout the world. Internet and social media were exploited by the Holy See adapting the apostolate to the new way of communicating. Each pope’s choice to use new media reflected how they conceived the role of the papacy and more generally the Church. In other words, the adoption of the new media and therefore the way through which the papacy decided to communicate to its flock had ecclesiological, theological, and of course political reflections. The chapter provides an overview of the relationship between the popes and the means of mass communication from Pius XI to Francis I. It shows that even when the popes were imbued with an anti-modern culture, they grasped the opportunity to fulfill their task of Catholic propaganda instead of demonizing the new inventions.