The correlation problem of postmodernism and modernism is not solved definitely in philosophy. The widespread point of view on possible drawing a parallel between them also is interpreted differently. Some supporters of postmodernism and modernism relationship consider that the basic conceptual theses of postmodernism have been formed due to nonviability of modernism. There are some interpretations of postmodernism among which it is possible to note the postmodernism characteristic as transition to something essentially different and its estimation as the continuation of modernism. The seeing of the relationship between postmodernism and modernism is caused first of all by a prefix “post” which refers to condition, following the given one, i.e. the term “postmodernism” means literally what goes after “modernism”. The given connection can be interpreted as genetic. The connection between postmodernism and modernism and their philosophical bases can be considered in a number of discourses, each of which discloses the various aspects of the problem. In some cases postmodern is defined as denial of modern or its overcoming. However, postmodernism is characterized by pluralism and unlike any anti-modernism includes modernism. At the same time as uniting factor of modernism and postmodernism the deep, typological relationship based on an idea of total and revolutionary break off the whole old world and its history is underlined. The given approach contradicts that postmodernism in most cases is a conscious dialogue with the past what has directly something in common with that postmodernist pluralism includes all the past and the present. One more prism through which the parallel between postmodernism and modernism can be drawn is a dialogue where dialogic nature of postmodernism is opposed to monologicality of modernism. The other prism – postmodernism includes poststructuralism, and modernism is identified with structuralism. Proceeding from the above-stated, it is possible to notice that “modernism” and “postmodernism” are not identical, but closely connected with each other conceptually. Both are an integral part of the characteristic of modernity and make up the present cultural context. The given theses cause the necessity of the philosophical analysis of the given concepts – modernism and postmodernism – with regard for the different approaches and deducing the pivotal parallels between their basic regularities.