The music of Dmitriy Shostakovich has typically been regarded as containing a semantic message, that reflected the political environment in which he composed. Such interpretations inadvertently relegated his works to little more than political propaganda, disregarding not only his artistic skill but the non-political purport of his music. Other studies focused on the music alone, ignoring the multi-dimensional nature of his works. Both approaches neglect an essential point, fundamental to the understanding of the traditional Russian perception of the arts. According to this tradition, an interrelationship between artistic technique and ideological content is the main aesthetic criterion. This study views music as a form that purports semantic content. As such, it correlates with other, mainly visual and verbal, forms of expression and communication. On the basis of this premise, this study investigates the musical manifestation of four semantic modes - irony, satire, parody and the grotesque - all of which are related to the comic. These four modes are analysed as specific cases of the overall semantic structure of ambiguity. Subsequently, a correlative structure of musical ambiguity is drawn. Thus the correlations between the musical, visual and verbal modes of expression are made principally on the basis of structural parallelism. Within the greater semantic web, music has a continuous interrelationship with other cultural units. In order to understand this interrelationship, some understanding of those cultural units is needed. Therefore irony, satire, parody and the grotesque are inspected as philosophical approaches, as creative principles, and as artistic techniques. Special attention is allotted to particulars that are characteristic of the Russian culture. Therefore, musical examples that correlate with the above modes and their techniques are analysed on the basis of their cultural associations and characteristics. These analyses are then compared with parallel examples from the works of Dmitriy Shostakovich, thus clarifying some former unacknowledged compositional techniques and characteristics of his music.