A Supposedly Fun Thing I'll Never Do Again

Describe the ways that irony features in the collection, both in terms of a theme and a device. Use textual evidence to develop an argument.

In the essay about tennis player Michael Joyce, to what extent does Wallace portray him as a tragic figure? Why?

In what ways do the essays in A Supposedly Fun Thing I’ll Never Do Again explore the ideas of Postmodernism? Use textual evidence to explore this aspect of the work.

What is Wallace’s relationship to the American Midwest? How do his essays reflect this dynamic?

What was the significance of tennis in David Foster Wallace’s life? How does the essay collection draw on this?

How does the use of footnotes evolve over the course of the essay collection? Why did Wallace feel so strongly about including them? Cite the book and any other sources you use in researching this topic.

Using textual evidence, examine how the character of Joe Briefcase reflects Wallace’s own biases.

Wallace profiles David Lynch and admires his work. To what degree does he like David Lynch as a person? Does it matter?