In this paper the development of social structures and generations in the GDR is outlined, and it is compared with developments of the “people’s republic” of North Korea in three aspects. Firstly, the emergence of a socialist establishment, that means larger social milieus which are apparently loyal to the state, is interpreted as a basis for stabilization in the GDR and in North Korea. Secondly, in the GDR Western oriented alternative milieus and subcultures became important actors during the political upheaval during the end of the 1980s. There is, however, no evidence of comparable intellectual or cultural counter-elites in opposition to the socialist establishment in North Korea. And third, the history of the GDR is distinguished by a sharply declining rate of integration of the younger generations into the socialist system. The last generations of the GDR are labelled with the adjectives “reserved and unadvised.” In contrast to the GDR, in North Korea each new generation seems to experience major historic events which had possibly had a constituting generative effect on some age cohorts. Thus, even the famine of the 1990s became a national challenge whose overcoming were laid in the responsibility of everyone, including the young generation. Finally, the conclusions of these differences between the former socialist states (using the example of GDR) and North Korea are discussed in the paper.