Abstract: While dreaming has garnered considerable attention as part of the discourse of modernity, waking dreams, dreams in which waking consciousness is present, have been considerably overlooked by humanities scholars. Walter Benjamin and Carl Jung were two theorists of modernity who sought alternate epistemologies to counter the homogenizing force of pure reason felt to dominate modern life, and wakeful dreaming played a crucial role in their respective projects. The similarities in their interests in dreams, however, are comprehensible only in light of the widely divergent conceptualizations of subjectivity and the messianic that undergird their writings. These profound differences indicate the epistemological breadth of waking dreams in the modern era.