This article examines the politics of irony and considers the role this ostensibly elitist mode of communication plays in a world characterized by economic inequality and unequal access to educational resources. Its study of the political uses of irony is grounded in an analysis of Søren Kierkegaard's dissertation On the Concept of Irony with Continual Reference to Socrates and Antonio Gramsci's prison notes on the usefulness of irony and sarcasm for revolutionary politics. The essay places Kierkegaard's canonical and conservative evaluation of irony in dialog with Gramsci's lesser-known writings on “passionate sarcasm” — a politically progressive manifestation of irony that vigorously ridicules the corruption of the social status quo while also building a positive movement for historical change. It argues that although Kierkegaard's philosophical study of irony is of enduring interest to scholars of classical Athens and nineteenth-century Romanticism, Gramsci's historicist evaluation of irony as a political tactic provides a more open and practical framework for the study of today's political satire. Although Gramsci's notes on irony and sarcasm are rooted in the cultural politics of early twentieth-century Europe, and interwar Italy in particular, many of their observations are applicable to the world in which we live. The article concludes by applying Gramsci's insights to select uses of irony in contemporary culture, including New Yorker cartoons and television programs such as The Daily Show.