David Foster Wallace Books in Order: Complete Guide & Best Starting Points

David Foster Wallace was the most technically ambitious American fiction writer of the 1990s and one of the finest essayists of his generation. His novel Infinite Jest (1996) is one of the most demanding and most celebrated in American literature — at over a thousand pages with hundreds of endnotes, it is the formal expression of his attempt to render the texture of contemporary American consciousness. He also wrote essays that are among the most discussed in recent literary non-fiction.

He died by suicide in 2008, having struggled with depression for most of his adult life. His writing about depression — both the explicit treatments and the implicit presence throughout Infinite Jest — has made him a figure of particular importance to readers who have experienced similar states.

Where to Start

A Supposedly Fun Thing I’ll Never Do Again (1997)

The right starting point for almost all readers. Seven essays — the title piece on a Caribbean cruise, a piece on David Lynch’s film sets, an extended analysis of television and literature, a profile of the tennis player Michael Joyce — introduce DFW’s voice in its most readable form: the intelligence, the self-consciousness, the footnote-dependent syntax, the capacity to move from comedy to philosophy within a paragraph. The cruise essay is the best introduction to what he does, and is also very funny.

Consider the Lobster (2005)

The second collection, more varied and in some ways more mature. Includes the title essay (a meditation on animal consciousness and the ethics of boiling lobsters, prompted by the Maine Lobster Festival), ‘Up, Simba’ (on John McCain’s 2000 campaign), ‘The View from Mrs. Thompson’s’ (9/11 in small-town Illinois), and a remarkable analysis of Fyodor Dostoevsky. The essays demonstrate DFW’s range and represent his essay voice at its fullest development.

The Novels

Infinite Jest (1996)

Wallace’s masterpiece and the most demanding major American novel of the 1990s. Set in a near-future America (with a satirical calendar system in which years are sponsored by corporations), the novel follows residents of an Enfield Tennis Academy and a nearby halfway house, converging around a film so entertaining it destroys the will to do anything but watch it. The novel is about addiction, entertainment, loneliness, and the specific failure of irony as a mode of being in the world — Wallace’s most sustained argument that genuine sincerity is possible and necessary.

The 388 footnotes are not optional — some contain essential narrative information. Many readers use two bookmarks.

The Pale King (2011)

The unfinished novel published posthumously, set in an IRS regional examining centre in Peoria, Illinois, in 1985. The premise sounds deliberately unpromising (boredom as subject matter) but the novel is Wallace’s attempt to argue that the capacity for sustained attention — for sitting with boredom rather than fleeing it — is one of the most important and most threatened human capacities. What exists is extraordinary; the absence of what was never written is one of literature’s genuine losses.

The Short Fiction

Brief Interviews with Hideous Men (1999)

A formally experimental collection in which the interview subjects are men, the interviewer is never represented, and the questions must be inferred from the answers. The stories are about misogyny, self-deception, the performance of authenticity, and the specific failures of men in contemporary America. Some of the most formally adventurous fiction DFW wrote, and the most difficult of his book-length works for readers who come to him through the essays.

Complete Bibliography in Order

Reading Order Recommendations

New to DFW: A Supposedly Fun Thing → Consider the Lobster → Infinite Jest (if the essays work).

Fiction first: Infinite Jest → Brief Interviews with Hideous Men → The Pale King.

Chronological: Girl with Curious Hair → A Supposedly Fun Thing → Infinite Jest → Brief Interviews → Consider the Lobster → The Pale King.