Is it possible to reconcile the spectacular approach of the media with the inner nature of the spiritual? Can one imagine the presence of religions within an ambience of entertainment? There always were tensions between religions and plays and games. Religions feared theatre, play, music, arts, dance, cards, and media, of course. Why are play and entertainment considered to be so dangerous? Would it be a better approach to discern true spiritual openings through play, and through media entertainment? In this chapter, the authors discuss the point of views of an historian, a film director, communication researchers, a philosopher, sociologists, and anthropologists, who offer a refined understanding of the capacity of playing to reveal the human search for meaning and spiritual journey. Play, and certainly media entertainment, can open humans to their own various potentialities, giving significance to their relation with the world and with other humans, and so with the sacredness. However, this can be done only if one respects the typical languages of the media made out of narratives and storytelling, which implies capacity of creativity in arts and rhetoric, combined with respect for ethical and spiritual dimensions of believers.