Where to Start with David Foster Wallace: A Reading Guide
Where to start with David Foster Wallace — whether to begin with Infinite Jest, Brief Interviews with Hideous Men, or The Pale King. A complete reading guide.
David Foster Wallace (1962–2008) is the American novelist whose combination of maximalist formal ambition, encyclopaedic cultural knowledge, and urgent moral seriousness made him the most discussed serious American fiction writer of his generation. His fiction is difficult — long, footnoted, formally fractured, emotionally demanding — and it demands commitment from its readers; but it also offers pleasures that no other American writer of his generation can match: genuine comedy, genuine pathos, a prose style that can move between registers (formal academic, vernacular, technical jargon, genuine tenderness) in a single paragraph. He died by suicide in 2008 at the age of 46.
Where to Start: Infinite Jest (1996)
The only starting point — and one of the most ambitious American novels of the twentieth century. Set in a near-future North America where calendar years are sponsored by corporations (‘the Year of the Depend Adult Undergarment’), the novel interweaves two primary locations: Enfield Tennis Academy, an elite junior tennis school in Boston, and Ennet House Drug and Alcohol Recovery House nearby. At its centre is the film ‘Infinite Jest,’ an entertainment so pleasurable that viewers cannot stop watching it — a McGuffin that allows Wallace to explore his central concerns: addiction (to substances, to entertainment, to irony, to comfort), loneliness, the possibility of genuine connection, and what it would mean to live sincerely in a culture that makes sincerity impossible.
The novel is over a thousand pages long and has several hundred endnotes, some of which are longer than chapters; its chronology is fragmented and its cast is enormous. It is not easy. It is also one of the most rewarding novels in American literature, and its comedy — in the tennis academy sections especially — is genuinely funny.
Brief Interviews with Hideous Men (1999)
Wallace’s short fiction collection and the best shorter introduction to his concerns. The title series — a collection of numbered ‘interviews’ with men who speak at length about their attitudes toward women and relationships, while the interviewer’s questions are left blank — is Wallace’s most direct confrontation with male self-justification and the distance between how people explain themselves and what they actually are. The collection also contains formally inventive stories about suicide, television, sexual violence, and the impossibility of genuine communication.
The best short entry point for readers who want to test their engagement with Wallace’s voice and concerns before committing to Infinite Jest.
The Pale King (2011)
Wallace’s posthumous and unfinished novel — assembled from drafts left at his death and published by his editor Michael Pietsch, who has described the choices he made in organizing the fragments. Set at an IRS examination centre in Peoria, Illinois in 1985, the novel follows a group of tax examiners doing work of almost inhuman tedium — and asks whether sustained, unglamorous attention to boring work is not, in fact, a form of ethical heroism.
The novel is incomplete, and reading it requires accepting what it cannot be. But it is also — in its completed sections — among the most interesting fiction Wallace ever produced, and its meditation on attention and boredom feels prescient in an era of chronic distraction.
Reading David Foster Wallace
Wallace’s fiction asks more of its reader than almost any other major American novelist — more time, more patience, more willingness to sit with difficulty and confusion before the shape of things becomes clear. But it also gives back more: a prose that can achieve genuine emotional directness after pages of ironic indirection, a comedy that is genuinely funny, and a moral seriousness about the problem of how to live with genuine care and attention in a culture designed to prevent both. Begin with Infinite Jest — there is no real alternative. For those who want a shorter test first, the essays are the most accessible and immediately pleasurable Wallace.
Frequently Asked Questions
Where should I start with David Foster Wallace?
Infinite Jest (1996) is the only place to start — it is his masterpiece and the most complete expression of his vision, concerns, and method, and no other work prepares you for it as adequately as simply reading it. At over a thousand pages with several hundred endnotes, it is genuinely demanding, and many readers do not finish it; but it is also genuinely rewarding in a way no shorter entry point can replicate. Brief Interviews with Hideous Men is the best alternative for readers who want a shorter introduction to his fiction; the essays (particularly those collected in Consider the Lobster and A Supposedly Fun Thing I'll Never Do Again) are the most accessible Wallace and often recommended as a first step.
What is Infinite Jest about?
Infinite Jest (1996) is set in a near-future North America where years are sponsored by corporations, and centres on two institutions: Enfield Tennis Academy, an elite junior tennis school in Boston, where Hal Incandenza (whose father, a filmmaker, has recently committed suicide) is one of the students; and Ennet House Drug and Alcohol Recovery House nearby, whose residents include Don Gately, a recovering Demerol addict. The novel's central McGuffin is the film 'Infinite Jest' — an entertainment so pleasurable that viewers lose the will to do anything but watch it — which various parties are seeking for political purposes. The novel is about addiction, entertainment, loneliness, the pursuit of meaning, and the tension between irony and sincerity in American culture.
Is Infinite Jest worth the difficulty?
Infinite Jest is genuinely difficult — its length, its footnotes (some of which are longer than chapters), its fragmented chronology, its large cast, and its demanding prose all require sustained commitment. Many readers find the first 200 pages the hardest and the novel easier once the characters are established; many readers do not finish it. Whether it is 'worth it' depends on your tolerance for difficulty and your interest in Wallace's themes (addiction, loneliness, American entertainment culture, the possibility of genuine sincerity). For readers who engage with it fully, it is one of the most rewarding novels in American literature. For readers who bounce off the difficulty, the essays are a better entry point.
What is The Pale King about?
The Pale King (2011) is Wallace's unfinished posthumous novel — assembled from drafts he left when he died in 2008. Set at an IRS tax processing centre in Peoria, Illinois in 1985, it follows a group of IRS examiners whose work requires almost superhuman levels of sustained attention to detail. The novel is Wallace's sustained meditation on boredom, attention, and the ethical value of doing unglamorous work with genuine care. Published posthumously and incomplete, it is a remarkable fragment of what might have been his masterpiece.
