The concept of irony is difficult to pin down, difficult to capture. This book is a critical examination of how Søren Kierkegaard and the pragmatist Richard Rorty approach the complex subject of irony. Gregory L. Reece traces the development of the philosophical concept of irony from Socrates to Hegel, Schlegel, Kierkegaard and Rorty, while addressing the very question that is central for both Kierkegaard and Rorty, the question of the relationship of ironic philosophy to an ironic life. Must ironic philosophy result in what Kierkegaard calls infinite, absolute negativity or in what Rorty describes as doubt and meta-stability? Gregory L. Reece argues that the answer is no, and that the belief that it must is based on an important philosophical mistake which in different forms is committed by both the early Kierkegaard and by Rorty. The insights of these philosophers, as well as those developed by Wittgenstein, are used to develop the beginning of an ironic philosophy of religion. Specifically, this work follows Kierkegaard and pursues these questions with special concern for the relation of ironic philosophy to religious belief.