In academic circles, the extent to which ideas of Austrian-British philosopher Ludwig Wittgenstein (d. 1951) are comparable to Zen Buddhist thought has been explored since at least 1958 with the publication of Paul Wienpahl’s article “Zen and the Work of Wittgenstein.” Articles written on the subject tend to focus on two aspects of Wittgenstein and Zen. One is the goals, namely the aim of Zen Buddhist practice compared with what Wittgenstein believes should be the aim of all philosophy. The other is the methods, namely traditional pedagogies used in Zen Buddhism to achieve Zen’s aim compared with how Wittgenstein believes philosophy can achieve its only legitimate aim. This amounts to comparing primarily the Zen ideas of satori, mushin, and kōans with the Wittgensteinian ideas of “complete clarity,” “just playing the game,” and “the only strictly correct method,” respectively. I argue that the accuracy of the comparisons made in scholarly works is lackluster until significant improvements begin around 1977. While analyses by Wienpahl (writing in 1958) and John Canfield (writing in 1975) leave much to be desired, analyses beginning with D. Z. Phillips and Dick Garner (both writing in 1977) more accurately represent the similarities and differences between Wittgensteinian and Zen thought. This paper leaves the reason for this phenomenon open to questioning, but invites the possibility that the improvements reflect increased exposure to authentic Zen thought by Western scholarship.