The boundaries between news and entertainment, and between public affairs and pop culture, have become difficult if not impossible to discern. At the intersection of those borders sits The Daily Show with Jon Stewart, a hybrid blend of comedy, news, and political conversation that is difficult to pigeon hole. Although the program often is dismissed as being “fake” news, its significance for political communication may run much deeper. This study first locates The Daily Show within an emerging media environment defined by the forces of technological multiplication, economic consolidation, and discursive integration, a landscape in which “real” news is becoming increasingly harder to identify or define. It then offers an interpretive reading of the program that understands the show not as “fake news,” but as an experiment in journalism. It argues that the show uses techniques drawn from genres of news, comedy, and television talk to revive a journalism of critical inquiry and advance a model of deliberative democracy. Given the increasing popularity of the program, this essay concludes that The Daily Show has much to teach us about the possibilities of political journalism in the 21st century.