The article revisits classical debates about the positive and negative relation of popular culture and socio-political developments with regard to the Arab world. Within the Frankfurt School and modern Cultural Studies at times contradictory approaches to the role of entertainment in political culture are being debated. In Islamic and Middle Eastern Studies rather positive readings of entertainments’ political potential seem to prevail. During the “Arab Spring” the impact of participatory values promoted by both popular culture and the new social media (“entertainment is political”) appeared to be actually tangible. The article discusses the dynamic relation of entertainment television and individualization on a theoretical and empirical level. On the basis of a large body of follow-up discourses of media reception (group discussions) with young Egyptians during the time of the “Arab Spring,” we ask whether contemporary television shows promote both individualization on a cognitive, affective and practical level of experience as well as the appreciation of individualization as a social value. We argue that popular culture reveals tendencies of differentiation and modernization in Arab societies, which are all too often described as “collectivistic.” The case study shows that critical faculty, media literacy and the appreciation of individual articulation can be triggered by entertainment. Moments of “ironic pleasure” and transitions of simulated empathy and stimulated action are discussed.