This essay explores Wittgenstein’s encounter with Stumpf’s work in Tone Psychology during a rarely studied period in Wittgenstein’s early career when he worked as a researcher in Myers’s laboratory for experimental psychology in Cambridge. I argue that Stumpf’s emphasis on the notion of musicality as the ability to characterize what is ‘musical’ about music troubled Wittgenstein’s initial formulation of his career-long adherence to the comparison between language and music. In the Tractatus the importance of internal projective relations far exceeds that (...) of arbitrariness in language. This results in the curious elision of musicality in the Tractatus, as shown in his gramophone analogy. The acknowledgment of the enormous complexity pertaining to the facts of human life remained underdeveloped in Wittgenstein’s philosophy until the anthropological turn in his middle-period. Only then do we see the blooming of the language-as-music simile and its eventual impact on Wittgenstein’s later philosophy. (shrink)