In this paper, I show that our ability to understand a piece of music as a gestalt, a cohesive cognitive unit separate yet emerging from the summation of its constituent parts, is shaped at large by enculturated patterns of music cognition and expression. I do this by examining West African and Western music culture’s respective dispositions towards orality or literacy which are evident in their pedagogies. Juxtaposing these pedagogies makes clear the kinds of oral and literate means of transmission and thinking by which individuals of these music-cultures form orientations, the point from which one “feels” a music structure’s rhythmic and phrasal attributes, and, ultimately, gestalts. When individuals encounter a different mode of cognition and expression, one that has not been culturally prescribed to them, gestalt formation can become impeded due to an incongruity of orientation between music structures resulting in their inadequate integration. I use my own experiences as examples to explain my claims.