It is the aim of this work to examine the pivotal role of Johann Joachim Winckelmann (1717–1768) as a judge of classical sculpture and as a major contributor to German art criticism. John Harry North seeks to identify the key features of his treatment of classical beauty, particularly in his famous descriptions of large-scale classical sculpture. Five case studies are offered to demonstrate the academic classicism that formed the core of his philosophy of art. North aims to establish Winckelmann’s place in the development of the German language. His prose contributed to a literary style that was suitable for the expression of an emotional response to visual experiences. His use of rhetoric in the assessment of classical art, however, make his judgements propagandist rather than analytical. The published works of Winckelmann, his draft essays and his collected private correspondence are advanced as criteria in the evaluation of his impact on the development of German classicism that culminated in the Weimar group of poets and writers. His Grecophile enthusiasm, however, led him to introduce stylistic categories in the development of classical marble sculpture that are no longer regarded as truly reflecting the evolution of Greco-Roman art. Thus his historicity and his classification of styles remain in doubt. Winckelmann proposed that the training of modern artists should concentrate on the observation and imitation of classical models instead of looking to nature as the source of inspiration. This plan succeeded to some extent in the generation that followed his untimely death. Throughout the succeeding century, artists and their sponsors did favour classical models and developed stylistic classicism in European freestanding sculpture, in painting and in architecture.