The purpose of this comparison and analysis was to examine the tenets of expressionism and existentialism as found in the aesthetic theories of Robin G. Collingwood and Eugene F. Kaelin, respectively. It was felt that both aesthetics proper, as a philosophic concern, and educational practices in art could benefit by the tenets of these two theories. In addition, many of the concepts explored were found to be mutually complementary not only in a logical sense but also in terms of clarifying the process of creation of works of art as well as contributing a pellucid view of response to art works.