This is a provocative account of pianist Glenn Gould's intellectual and musical thought. Gould was a philosopher who incessantly pursued wisdom through his art. If the reader follows Gould's ardent campaign through the metaphorical thicket found in his ideas, a compelling Gouldian model for a philosophy of music unfolds. Gould argues that music is not only a reflection of social dynamics, but could also be a tool for the betterment of society. The original methodology conceived and implemented in this study contributes an important design for subsequent historical/philosophical studies, particularly in music education.