The relationship between the law and the essay, this chapter shows, is visible in the etymology of the latter. Derived from assayer, to try, and essai, or trial, the etymology connotes action, endeavor, and experiment aimed at proof leading to judgment. However, the essay as literary genre is often marked not by the finality of judgment but by levity, incompletion, indigestion, distraction, and exploratory attempts. The apparently antithetical senses of the essay – as comedic and judicial, frivolous and veridical, theatrical and juristic, popular and esoteric – are key to understanding its later development and certain specifically distinctive features of the “American” genre of legal exploratory discourse. This chapter shows the influence of pragmatism and egalitarian realism on American legal writing, offers examples of the legal polemics that unfolded in the pages of important American law journals, and argues that the importance of the essay form is to clear a space, to act out in ideas what practice has not yet tested, and so to become the theater that stages in advance the future of law.