This study develops an interdisciplinary approach to the analysis of the cultural history of the German Democratic Republic, examining the interaction between intellectuals and Party functionaries from a literary and historical perspective. Divided into three case studies, the work focuses on writers positioned along a spectrum of conformity and dissent and who had quite different relationships to political power: Hermann Kant, Stefan Heym and Elfriede Brüning.Drawing on and comparing unpublished archive material, autobiography and the literary output of the three named writers, this study brings to the fore the ambiguities and contradictions of intellectual life in the GDR. Tensions between the different sources point towards tensions inherent in the subject positions of writers, publishers, reviewers and cultural authorities. This granular approach to the study of GDR cultural history challenges top-down interpretations and builds into a theoretical understanding of GDR cultural life based on the concepts of ambiguity and ambivalence and the increasing fragmentation of ideology. Comparison with other spheres of GDR life points towards the significance of these concepts for the study of East German society as a whole.