Inquiring into the role that paradox and double-binds play within the work of Alan W. Watts, this essay addresses a quintessential theme in Watts’ philosophy: a twofold sense of ontological estrangement (i.e., from oneself and from the cosmos). Such paradoxical separation constitutes an ontological double-bind and is referred to herein as life’s ultimate riddle. Based on an exegesis of 73 of Watts’ books, articles, and secondary sources, this essay presents what is called Wattsian double-bind theory, which extends David Smith’s (2010) triadic thesis of Watts’ mature works featuring a three-fold conceptual structure: the field, the double-bind, and play. Following an overview of Wattsian ontology, this essay then aims to (a) identify Watts’ double-bind framework informed by paradox, koans, double-binds, and their resolution via acceptance; (b) clarify the similarities and vast differences between Wattsian and classical Batesonian double-bind theories; and (c) reveal the interconnected elegance of the former, as it occurs in the themes of language, time, perception, identity, science, and religion.
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