Where Adam Smith’s The Theory of Moral Sentiments (1759) extends the domain of spectatorship beyond the ocular realm and claims that we must become the impartial spectators of our own character and conduct, Jean-Jacques Rousseau’s Rousseau juge de Jean-Jacques, Dialogues (1776) also attempts to probe beyond the visual surface to examine through careful study the constitution of another, who is actually himself. This chapter traces a Smithian sentiment in the radical division of the self dramatized in Rousseau’s fictional autobiographical Dialogues, emphasizing Rousseau’s attempt to liberate his own gaze and render an unbiased judgment upon himself. Although Rousseau does not write in direct discourse with Smith, he applies a strikingly similar rhetorical device to the spectator within the dialogic structure of his apologia. Reading Rousseau alongside Smith resituates the Dialogues not as a work of madness, as it has frequently been interpreted, but rather as an unrelenting struggle for justice.