This chapter offers a brief scholarly overview of the ancient art of rhetoric and outlines rhetoric's philosophical and practical relationship to literary criticism. Beginning with the issues raised by the classical rhetoricians, this chapter focuses on the critical rhetorical philosophy developed within the Scottish Enlightenment, from which arose literature as a modern academic field. The work of Adam Smith is used as a rubric by which to outline the interdependent moral, linguistic, psychological, rhetorical, and philosophical considerations that underpin eighteenth-century rhetoric and develop literature and criticism as essential to moral education. This chapter argues that the philosophical relationship between rhetoric and literary criticism is inherent and the ideological issues raised between them critical to the current state of the humanities.