David Foster Wallace’s works engaged with his literary moment–roughly summarized as postmodernism–and with the author’s historical context. From the famous Complexity of novels such as Infinite Jest to the direct critique of American culture in his essays, his works have at their core basic themes, such as self-understanding, connecting with others, ethical behavior, and finding meaning. The essays in this volume suggest ways to elucidate Wallace’s philosophical and literary preoccupations as students continue to contend with urgent issues, both personal and political, through reading literature.Part 1, Materials, offers guidance on editions of Wallace’s works and critical responses to them. The essays in part 2, Approaches, discuss teaching key works and genres in high schools, first-year undergraduate writing classes, American literature surveys, and world literature classes. They examine Wallace’s social and philosophical contexts and contributions, treating topics such as gender, literary ethics, and the culture of writing programs.