The East German musical youth film Heißer Sommer (“Hot Summer”, dir. Joachim Hasler, 1968) was a smash hit in the summer of 1968. In the height of the Cold War and the transnational youth movements of the 1960s, a breezy teen film sporting Western fashions and music is hardly what one would expect DEFA, the GDR’s official film company, to produce. However, growing anxiety from the youthful revolutionary spirit of ‘68 on the one hand and dire desperation for the teenagers’ support on the other forced the GDR to resort to such measures. This article argues that Heißer Sommer’s success came from its rare ability to ‘speak the language’ of the youth, which allowed it to be a heavily didactic film without appearing so to its audience. By examining it through the prisms of generational conflict, Americanization, gender and sexuality, and the problem of individualism vs. collectivism, this article suggests viewing the film as a highly complex effort at effectively winning back the youth by teaching it that socialism can be fun.