Interactive entertainment poses particular regulatory challenges. More specifically, the democratization of technology and creativity has meant that there is no capacity for a governmental agency to effectively regulate the spread, and enjoyment, of allegedly problematic expressions. This article will explore this by contrasting the regulation of non-interactive entertainment (including Dada art and punk music) with more recent forms of (at times) transgressive expression (amateur pornography, video games and fake news). The analysis will be carried out in terms of the different motivations of the range of parties involved in the process (including creators, distributors, consumers and the broader public) and of the different conceptions of the consumer that are implicit in different... modes of regulation. The complexity of the interactions means that there is no single regulatory solution; the historical exploration of the issue, nonetheless, suggests that interactivity may be no worse for society than the earlier forms of expression that were, at the time, deemed to be a threat to its moral fabric.