Comedy has a notoriously unstable relationship to authority. On the one hand, comedy offers a subversive de-masking of the claims of authority, bringing it down to earth and exposing its functioning. On the other hand, comedy can also, as in the case of the Shakespearean fool, give authority a necessary flexibility and the capacity to absorb criticism. In the present moment we witness, in the figure of the ‘postmodern boss’, the combination of master and fool: an authority which presents itself as comic, as capable of laughing at itself, but which remains in charge. To analyze this figure I turn to Lars Von Trier’s self-declared ‘harmless comedy’ The Boss of it All (2006). While Lars Von Trier’s films have attracted considerable critical attention, especially from Lacanian critics, this has been particularly focused on its melodramatic figurations of female excess, sacrifice, and jouissance. In fact I argue this seemingly ‘minor’ work, an office comedy no less, offers a capacity to critique the integration of comedy and authority. The film does so by taking the appearance of authority seriously, and so indicating how authority constantly displaces itself through ‘comic’ masking of its function. The truth lies not beneath the mask, but in the masks, especially the comic mask, that authority presents to us. In this way The Boss of it All allows us to trace what I call ‘the psychopathology of everyday authority’.