The culture at the ducal court of Sigmund and Albrecht IV of Bavaria-Munich was characterised by a coexistence of traditional as well as novel concepts and interests, which were expressed in the dukes’ artistic, architectural and literary patronage. Apart from examining the orthodox means of aristocratic self-aggrandizement like jousting, clothes, decorative arts and precious, exotic objects, this thesis discusses ‘innovative’ tendencies like the forward-looking application of retrospective motifs, historicising styles as well as the dukes’ genealogy, the ducal government’s imprint on the territory and the aesthetic qualities of the landscape. The study of a selection of buildings and works of art with the methodologies of the stylistic analysis, iconology and social history emphasises the conceptual relations between the ducal court’s various cultural products, which were conceived as ensembles and complemented each other. The elucidation of their meanings to contemporaries and the patrons’ intentions is substantiated with statements in contemporary written sources like travel reports, chronicles and the ducal court’s literary commissions. The principal chapters explore three thematic strands that are idiosyncratic for the culture at the court of Sigmund and Albrecht IV between 1460 and 1508, because they were consistently realised in several buildings and works of art. The first chapter provides an overview of the history of Munich, the Duchy of Bavaria and the Wittelsbach dynasty. The second chapter explores the princely self-conception at the threshold of the Late Middle Ages and the Early Modern Era by considering the application of clothes, decorative arts, knightly skills, exotic animals, and monuments of the patrons’ erudition as means of social communication and differentiation. The third chapter considers the dukes’ awareness as well as ‘manipulation’ of their genealogy and history as a forward-looking means for legitimating and realising their political objectives. It also examines the symbolism and origins of historicising motifs in art and architecture like the Church of Our Lady’s bulbous domes that acted as markers of the ducal sepulchre. The fourth chapter scrutinizes the impact of the dukes’ government and artistic as well as architectural patronage on their territory. It also considers emergence of poly-focal panoramic views from the interiors of castle and palaces into the surrounding countryside by examining the origins of this phenomenon and the perception of the landscape’s aesthetic qualities.