Over the past few decades, music theorists such as Allen Forte, Martin Eybl, and Nicholas Cook have noted connections between the psychoanalytic theories of Sigmund Freud and the music theories of Heinrich Schenker. This paper fills an important gap in this discussion by demonstrating a more direct connection between Schenker and Freud. It examines an article by Freud, Die Wege zum Glück, which is found as a clipping from Neue Freie Press in Schenker's Nachlass. Die Wege zum Glück is an excerpt from the second chapter of Freud's Das Unbehagen in der Kultur. This paper will explore direct connections found between Freud's Das Unbehagen in der Kultur and the writings of Heinrich Schenker, specifically passages found in Harmonielehre and Der freie Satz. These passages are significant because they confirm several similarities in Freud and Schenker's thinking. This paper will explore these similarities which include common attitudes about the nature of society and culture, the instinctual drives (both musical and psychical) that inspire conscious manifestations of unconscious substructures, and the source of beauty. A comparison of Die Wege zum Glück with Schenker's writings reveals that Schenker, like Freud, saw "the love that procreates" as the highest of instinctual processes.