This chapter argues that the shift toward individualized entertainment engendered by digital disruption and Technology-Media-Telecommunications convergence is heralding a new phase in Indian Media and Entertainment industries on global, national, regional and local scales that the author describe as post-Bollywoodization. It examines the rise of individualized entertainment in relation to the historical legacy of “family viewing” as a state-sponsored nationalist ideology in India. The chapter outlines the emerging strategy of Consumer acquisition, retention and transaction that traditional and new media organizations alike are embracing to target the complex mobilities of their constantly shifting audiences. It is important to note that the concept of individualized entertainment is hardly representative of the current industry practices or of media consumption patterns in India or in other globalized markets today. The shift away from the ideology of a “national family” of audiences toward the delivery of individualized entertainment through digital platforms is clearly challenging the Bollywoodization of the Indian media and entertainment industries.