This thesis contends that the Lehrstück (Learning Play) created by Bertolt Brecht and his composer collaborators – Weill, Hindemith, Eisler, Dessau, and Schwaen – is a dialectical genre that merges the realms of music and text in an interconnected, dialogic manner that is informed by Taoist and Marxist dialectical thought. Commencing with an original in-depth elaboration of how the Lehrstück emerged within the socio-historical and aesthetic framework of Neue Musik (New Music) in Weimar Germany, this thesis illuminates the musical and social strategies of Neue Musik, their impact on the Lehrstück genre, and their usefulness for the development of dialectical music. This thesis also investigates the nature of all Lehrstück collaborations, arguing that they demonstrate a prime example of collective creativity between writer and composer, in which the literary and musical realms are equally involved with, and challenged by, each other. The main argument of the thesis is that music and music-text relations in the Lehrstück are both the product and proponent of a dialectical method for analysing and conveying social realities. The thesis provides clarification of both dialectically conceived music and of how it relates to the text, by applying qualitative content analysis to the music of all six Lehrstücke. This analysis is informed by Jürg Boner’s notion of dialectic as “unity of representation and critique”. Within this unity, musical Verfremdung (defamiliarization) assists in the depiction of the social realities portrayed in each Lehrstück as contradictory, erratic and in a constant state of change. My analysis reveals and elaborates on the various modes of Verfremdung that occur in the Lehrstück choruses, solo vocal forms and purely instrumental pieces. It does so through organizing these modes of musical Verfremdung into a taxonomy consisting of three complexes: 1) musical parody, 2) the outer musical form (style, compositional technique, and instrumentation), and 3) the inner musical form (melody, harmony, and rhythm). This thesis aims to provide a detailed and accessible music-text analysis that results in an illumination of how dialectical music encourages both the performer and the audience participant to take an inquiring attitude towards the events represented and to commence their own social critique.