By saying that punishment was festive, Nietzsche called attention to a contradiction in modern life which affected the mechanisms through which the pleasure of punishment was generated. It may be festive, but not in the sense of joining-in with everybody else, undisturbed by morality or shame. Instead, what provided pleasure was the participation in something everyone knew was forbidden. The element of prohibition was integral to the pleasure. Still and in fact more than ever, pleasure had to be taken seriously, since it had lost none of its disruptive force. Nietzsche, and later Freudian psychoanalysis, picked up what had been sidelined in the historic cleansing of punishment, from Plato and onwards: the disproportionate, all the passions, and the illegitimate – and turned that into an area of investigation. This chapter is entirely devoted to obscene enjoyment as a specifically modern pleasure of punishment. Each section is organized around authors who stress different aspects of the enjoyment: Lacan discussed the obscene enjoyment of being implicated in transgressive punishment, Žižek discussed the guilt-ridden enjoyment of guarding inglorious secrets, and Nietzsche the sense of power in partaking in unrestrained assertion, as spectator. Contemporary examples regarding transgressive punishments are used to elucidate the different aspects.