This dissertation offers a critical analysis of Walter Benjamin's philosophy of language, compares it to Ludwig Wittgenstein's thought on language, and traces the historical foundation of both accounts of meaning to 18th and 19th century German philosophy.Benjamin's theory of language, espoused in early essays and in The Origin of German Tragic Drama, is notoriously dense and obscure. In elucidating it, I emphasize Benjamin's attempt to reorient the Kantian project around language – the medium in which knowledge is expressed – and his concern with the logical understanding of language gaining credence in the work of Russell and Frege in the early 20th century. The result is a radical model of the relationship between language, experience, and world that sees "absolutely everything" as linguistic in a broadened sense and which sees the logical or designative capacities of language as grounded in an aesthetic foundation. The famous "Epistemo-Critical Preface" to his book on German tragic drama is an extension of the theory of language into a metaphilosophy. Benjamin develops full-fledged theory of concept-use and a view of philosophy as criticism. These ideas have various sources, but their foundation is in the expressivist philosophy of Hamann, Herder, and Schlegel, the main subject of Benjamin's dissertation The Concept of Art Criticism in German Romanticism.This expressivist tradition is influential in the 19th century in the works of, among others, Nietzsche and Fritz Mauthner, whose import for the late Wittgenstein has been recognized. I read the turn in Wittgenstein's thought as a turn back to this tradition. The Philosophical Investigations radicalizes certain strains in Mauthner's thought, ridding it of some of its empiricist biases and drawing expressivism closer to its roots in Hamann's work. The work of the late Wittgenstein's shares much of its impetus and some of its substance with Benjamin's theory. The two are read as complementary to one another, sharing, among other things, comparable critiques of empiricism and comparable accounts of concept use, linguistic understanding, and the relation between experience and language. Ultimately, the comparison breaks down over Wittgenstein's account of the "experience of meaning," which is subordinated to his account of meaning as use. I argue that Benjamin's theory of language can productively address some unresolved issues in Wittgenstein's understanding of meaning.