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

A Defining Voice of His Generation

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Irony, Sincerity, and the Search for Meaning

A central concern of David Foster Wallace’s work is the relationship between irony and sincerity, his diagnosis of the pervasive irony of contemporary culture and his search for a way beyond it toward genuine sincerity, connection, and meaning. Wallace was deeply concerned with the pervasive irony and detachment of contemporary American culture, with the way that irony, cynicism, and self-consciousness had come to dominate the culture and to foreclose genuine sincerity, feeling, and connection. His work diagnoses this pervasive irony and searches for a way beyond it, toward a renewed sincerity, genuine feeling, and authentic human connection, and this search for a way beyond irony toward sincerity and meaning is among the central concerns of his fiction and essays. This concern with irony, sincerity, and the search for meaning gives Wallace’s work its depth and its distinctive significance, for he diagnosed the pervasive irony of contemporary culture and sought, against it, a renewed sincerity, connection, and meaning. His work grapples with the difficulty of achieving genuine sincerity and connection in a culture dominated by irony and detachment, and it searches for a way toward authentic feeling and meaning. For readers, Wallace offers a profound engagement with irony, sincerity, and the search for meaning, the diagnosis of contemporary irony and the search for a way beyond it toward genuine sincerity and connection. Irony, sincerity, and the search for meaning are central concerns of Wallace’s work, his diagnosis of the pervasive irony of contemporary culture and his search for a way beyond it toward genuine sincerity, connection, and meaning.

A Demanding and Rewarding Art

David Foster Wallace’s fiction is genuinely demanding, marked by its length, complexity, and formal challenges, but it rewards the reader’s effort with an intelligence, depth, and humanity that have made it among the most admired and influential work of its era. Wallace’s fiction, particularly his monumental Infinite Jest, is notably demanding, marked by its great length, its formal complexity, its difficult structure, and its intellectual challenges, requiring real effort and commitment from the reader. Yet this demanding art rewards the effort it requires, offering an intelligence, depth, humanity, and brilliance that have made Wallace’s work among the most admired and influential of its era. The demands of his fiction, its length, complexity, and formal challenges, are integral to its ambition and its achievement, and the reader who meets these demands is rewarded with a work of extraordinary intelligence, depth, and humanity. This demanding and rewarding character is important to understand in approaching Wallace, for his fiction asks much of the reader but repays the effort with the rewards of its intelligence, ambition, and humanity. For readers prepared to meet its demands, Wallace’s fiction offers a demanding but deeply rewarding art, an intelligence, depth, and humanity that reward the reader’s effort. A demanding and rewarding art marks Wallace’s fiction, genuinely demanding in its length, complexity, and formal challenges, but rewarding the reader’s effort with an intelligence, depth, and humanity that have made it among the most admired and influential work of its era.

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.