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Character analysis

Hugh Steeply

in Infinite Jest by David Foster Wallace

Hugh Steeply works as a field agent for the U.S. Office of Unspecified Services (O.U.S.), tasked with finding and neutralizing a dangerous entertainment cartridge called "the Entertainment," which is a film created by James O. Incandenza, in Infinite Jest. Steeply goes undercover, most notably disguised as "Helen Steeply," a large woman pretending to be a journalist profiling Orin Incandenza, whom the O.U.S. suspects may know something about the cartridge's distribution.

A key aspect of Steeply's role is his participation in the philosophical dialogue scenes set on an Arizona hillside. Here, he engages in lengthy, circular debates with Québécois wheelchair-assassin Rémy Marathe, discussing topics like freedom, desire, entertainment, and national identity. These fragmented conversations, spread across hundreds of pages, serve as the novel's ideological backbone, with Steeply embodying a broadly American liberal-individualist viewpoint that values choice — even when it's self-destructive — in contrast to Marathe's collectivist perspective.

Steeply's character is characterized by irony and concealment; his cross-dressing disguise reflects the novel's themes of performance and hidden identity. He is skilled and sardonic, but his confidence in American values is gradually undermined by Marathe's arguments. His backstory, especially his father's obsessive fixation on a TV game show, adds unexpected personal stakes to the novel's exploration of addictive entertainment, anchoring his philosophical discussions in real familial grief.

About this character

Form
Novel
Author
David Foster Wallace
First published
1996

The person01–03

01·Who they are

Who is Hugh Steeply?

Hugh Steeply is a field operative for the U.S. Office of Unspecified Services, a deliberately vague acronym that suits a deliberately vague man. Tall, broad-shouldered, and male, he spends much of the novel's present action dressed as "Helen Steeply," a female journalist—a disguise that requires industrial quantities of foundation, a wig, and considerable physical implausibility. Wallace describes the costume in almost comic terms, Helen being conspicuously large and not quite convincing, which is precisely the point: concealment in Infinite Jest is never seamless, and Steeply's cover reflects a culture skilled at performance but poor at genuine self-knowledge. He is sardonic, professionally fluent, and broadly representative of a certain American confidence—the belief that individual choice is its own justification, that freedom and desire are essentially the same thing. That confidence is what the novel targets.

02·Arc & motivation

What is Hugh Steeply's arc and motivation?

Steeply's mission is straightforward on paper: locate and neutralize the master copy of James O. Incandenza's lethal film, the Entertainment, which renders viewers catatonically pleasured to death. His cover as Helen Steeply is designed to get close to Orin Incandenza, whom the O.U.S. believes may be a distribution node. At the operational level, Steeply is competent and methodical. At the philosophical level, however, his arc is one of slow erosion. His repeated hillside meetings with Rémy Marathe—themselves a kind of addictive loop, each conversation circling back without resolution—gradually expose the fault lines in his worldview. He begins each exchange certain that American liberal individualism is defensible, even admirable, and ends each one slightly less sure. He does not convert, but he is demonstrably shaken. His personal history with his father gives this erosion private roots: Hugh watched a brilliant, sensitive man destroyed by obsessive fixation on a television game show, which means he has already lived, in miniature, the catastrophe the Entertainment threatens to inflict on an entire population.

03·Key moments

What are Hugh Steeply's key moments?

The hillside dialogues themselves are the defining textual event for Steeply, structured as interruptions spread across hundreds of pages—Sections 17, 28, 39, and beyond—so that readers experience the circularity Marathe and Steeply enact. When Steeply defends the right of individuals to choose their own pleasures, even fatal ones, Marathe's rejoinder—that a culture which cannot distinguish between a want and a need will choose the Entertainment freely and die freely—visibly lands. Steeply has no clean answer. Equally significant is the extended passage in which Steeply recounts his father's spiral into obsession with the game show Jeopardy!—staying up through the night, neglecting his family, his mind colonized by the show's rhythms. This backstory, delivered conversationally to Marathe, is one of the novel's quietly devastating sequences, transforming Steeply from ideological mouthpiece into a son who has already lost someone to the logic of compulsive entertainment. His undercover seduction of Orin, by contrast, registers as dark farce: Helen's improbable femininity charming an Incandenza who cannot resist the attention.

The cast04–05

04·Relationships

What are Hugh Steeply's most important relationships?

Steeply and Marathe form the novel's most explicitly dialectical relationship. They are nominal adversaries—Marathe is a Québécois separatist working with the Wheelchair Assassins, Steeply his O.U.S. counterpart—but both are effectively double agents, and both know it, which strips their exchanges of any pretense of pure opposition. What remains is something closer to friendship shaped by argument: two men who need each other to think. Marathe's collectivist ethics, his willingness to subordinate individual desire to communal survival, challenge Steeply in ways no American colleague could.

Steeply and Orin is a relationship built entirely on false premises. Orin's susceptibility to women's attention—itself a compulsion Wallace traces through the novel—makes him an ideal target for Helen Steeply. The manipulation is effective and faintly pitiful, a surveillance operation that mimics intimacy.

Steeply and James Incandenza never meet; James is dead. Yet the creator of the Entertainment is the gravitational center of Steeply's entire professional existence, making theirs a relationship conducted entirely through artifact and consequence.

05·Connected characters

How is Hugh Steeply connected to the other characters?

Rémy Marathe

Steeply's ideological sparring partner and nominal adversary. Their hillside dialogues — conducted in mutual awareness that each is a double agent of sorts — are the novel's primary arena for debating freedom, addiction, and national character. Marathe's arguments about the danger of absolute choice visibly unsettle Steeply's American certainties, and their relationship blurs the line between opponent and confidant.

Orin Incandenza

Steeply's undercover target. Disguised as journalist 'Helen Steeply,' he cultivates Orin to extract information about the Entertainment cartridge. Orin, characteristically susceptible to female attention, is manipulated without realizing it, making the relationship a dark comedy of seduction and surveillance.

James O. Incandenza

The O.U.S. investigation Steeply leads centers on James's film. Though James is dead before the novel's present action, his creation of the Entertainment is the gravitational force behind Steeply's entire mission.

Joelle Van Dyne

Joelle, as the veiled star of the Entertainment and a figure connected to its production, is a person of interest within the O.U.S. investigation Steeply conducts, linking her indirectly to his surveillance network.

Hal Incandenza

As a son of the Entertainment's creator and a resident of Enfield Tennis Academy, Hal exists on the periphery of Steeply's investigative interest, representing a potential thread connecting the Incandenza family to the cartridge.

Study06–07

06·Questions

Questions readers ask about Hugh Steeply

Who is Hugh Steeply's most important relationship in Infinite Jest?

Rémy Marathe is Steeply's most important relationship in the novel. Though nominal adversaries — Steeply works for the U.S. Office of Unspecified Services, Marathe for the Québécois Wheelchair Assassins — both are double agents who know it, which strips their hillside dialogues of pure opposition. What remains is something closer to a friendship shaped by argument, with Marathe's collectivist ethics persistently unsettling Steeply's American liberal-individualist certainties.

Why does Hugh Steeply dress as a woman in Infinite Jest?

Steeply disguises himself as "Helen Steeply," a female journalist, to get close to Orin Incandenza, whom the O.U.S. suspects knows something about the distribution of the lethal Entertainment cartridge. The disguise is played in almost comic terms — Helen is conspicuously large and not quite convincing — which Wallace uses deliberately to reflect a culture skilled at performance but poor at genuine self-knowledge.

What is Hugh Steeply's mission in Infinite Jest?

Steeply's mission is to locate and neutralize the master copy of James O. Incandenza's lethal film, the Entertainment, which renders viewers catatonically pleasured to death. Operating for the U.S. Office of Unspecified Services, he pursues leads through his undercover persona as Helen Steeply and through surveillance of figures connected to the Incandenza family, including Orin, Joelle van Dyne, and Hal Incandenza.

How does Steeply's father connect to the novel's themes of addictive entertainment?

Steeply's father became obsessively fixated on the television game show Jeopardy!, staying up through the night and neglecting his family until his mind was colonized by the show's rhythms. Recounted conversationally to Marathe, this backstory is one of the novel's quietly devastating sequences. It transforms Steeply from ideological mouthpiece into a grieving son who has already witnessed, in miniature, exactly the catastrophe the Entertainment threatens to inflict on an entire population.

What philosophical position does Hugh Steeply defend in his debates with Marathe?

Steeply defends a broadly American liberal-individualist position: that individual choice is its own justification and that freedom and desire are essentially the same thing. He argues that people have the right to choose their own pleasures, even self-destructive ones. Marathe counters that a culture unable to distinguish a want from a need will freely choose the Entertainment and freely die, a rejoinder to which Steeply has no clean answer.

Does Hugh Steeply's confidence in American values change over the course of Infinite Jest?

Steeply's confidence is gradually eroded, though he never fully converts to Marathe's collectivist view. He begins each hillside exchange certain that American liberal individualism is defensible and ends each one slightly less sure. His personal history — watching his father destroyed by a television obsession — gives this philosophical erosion private roots, suggesting his blind spot about addiction is not merely intellectual but deeply personal.

What is Hugh Steeply's relationship to James Incandenza, the creator of the Entertainment?

Steeply and James Incandenza never meet, as James is already dead before the novel's present action begins. Nevertheless, James's lethal film is the gravitational center of Steeply's entire professional existence, making theirs a relationship conducted entirely through artifact and consequence — Steeply pursues the meaning and location of a work made by a man he can only know through its devastating effects on others.

How does Steeply's undercover relationship with Orin Incandenza work?

Disguised as journalist "Helen Steeply," Steeply exploits Orin's well-established susceptibility to female attention to cultivate him as an intelligence source on the Entertainment cartridge. Orin is manipulated without realizing it, making the relationship a dark comedy of seduction and surveillance. Wallace frames it as faintly pitiful — an operation that mimics intimacy while hollowing it out entirely.

07·Essay angles

Use this in your essay

Tool · Essay angles

  • The father's fixation as microcosm

    Argue that Steeply's account of his father's *Jeopardy!* obsession is Wallace's compressed proof-of-concept for the Entertainment's threat, and that Steeply's blindness to the parallel undermines his ideological confidence.

  • Cross-dressing and the performance of identity

    Examine how Helen Steeply's implausible disguise participates in the novel's broader argument that American identity is itself a kind of costuming—maintained through repetition rather than essence.

  • Freedom as vulnerability

    Using the Marathe-Steeply dialogues, build a thesis on whether Wallace ultimately endorses, critiques, or refuses to resolve the tension between liberal individualism and communitarian self-protection.

  • The double agent as epistemological figure

    Both Steeply and Marathe occupy compromised positions of partial knowledge. Argue that their mutual double-agency makes genuine philosophical resolution structurally impossible in the novel.

  • Surveillance and seduction

    Analyze the Steeply-Orin relationship as a meditation on how entertainment culture and intelligence culture share techniques—both manufacture desire in order to extract information or compliance.

Infinite Jest

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