David Foster Wallace's literary reputation rests largely on his achievements in Infinite Jest (1996), a sprawling tale of tennis, familial relationships, conspiracies, drug dependence and a great deal more. Building on the themes and styles he had first explored in The Broom of the System (1987), a novel that tells of Lenore Stonecipher Beadsman's attempts to unravel some of the many mysteries that surround her, Infinite Jest tests the character and endurance of readers in ways that few books dare to do with its densely comic prose and a narrative that builds intricate interlocking arcs upon paranoid foundations.

Owing a great deal to John Barth, Thomas Pynchon and Don DeLillo, Wallace often acknowledged his debt to metafiction and was happy to pay homage to his postmodern ancestry. Wallace, though, was always concerned to do more than simply emulate. The challenge for him was to revivify their work and find a way, as he explained in “E Unibus Pluram,” to combine “neo-postmodern techniques” with “a genuine socio-artistic agenda.”Footnote ¹ Driving this ambition was the knowledge that the radical energy of metafiction's experiments had been dissipated. While praising Robert Coover and Vladimir Nabakov during an early interview with Larry McCaffery, he noted that their approach got “empty and solipsistic real fast” and went on to suggest that “by the mid-seventies, I think, everything useful about the mode had been exhausted.”Footnote ² Wallace's aim was to “get it over with, and then out of the rubble reaffirm the idea of art being a living transaction between humans.”Footnote ³

It is this search for a synthesis between the elaborate codes of literary experiment and a plain and unreflexive humanism that informs Wallace's work, a search that gives shape to Infinite Jest. At the heart of the novel is a very shaggy McGuffin – the mysterious movie said to have been made by James Incandenza, lost father to tennis prodigy Hal, the novel's immaculately stoned central protagonist. Infinite Jest, a.k.a. The Entertainment, is a film so transcendently amusing that it transports the viewer into a blissful state of catatonia. Because of this power, it becomes the focus for a series of slapstick quests, an object sought by various organizations including government agencies and the AFR (les Assassins en fauteuils roulants), a Québécois separatist group. For the AFR, the aim is to “secure the original Master, the auteur's own cartridge, from which all Read-only copies had presumably been copied,” and use it as a weapon against imperialism.Footnote ⁴ Like the soul of aesthetic radicalism lost to contemporary fiction and mourned by Wallace, the master tape, representing authenticity, rupture and rebellion, comes to haunt the text. It is not just out of reach, but out of time, an anachronism in a homogenized future that has seen the US transformed by corporate interests and absorbed into a single continental state, called, in terms typical of Wallace, ONAN, the Organization of North American Nations.

The desire to recuperate metafiction is, of course, like the pursuit of Infinite Jest the movie, quixotic. The truth is that there is little possibility of forging a functioning marriage between the formal freedoms found by Barth and Pynchon and an unreflexive humanism precisely because it was, in part, the interrogation of humanism's commonsensical values that gave metafiction its critical and imaginative energy in the first place. Beyond that, it is difficult to see how Wallace could ever have found a genuine radicalism while he remained committed to repeating an experiment that was first run thirty years before, no matter how brilliant the performance. In this regard, Infinite Jest is powerfully contradictory. More than just a piece of nostalgia, it is a novel caught in an ironic yearning for the authenticity and critical energy it sees in postmodernism's golden age.

Despite this paradox, or perhaps because of it, Wallace's novel remains very influential and it has had an important impact on the shape of contemporary American fiction, particularly on the work of those linked to Timothy McSweeney's Quarterly Concern, one of America's most distinctive literary magazines. Overseen by Dave Eggars, and promoting Jonathan Safran Foer, Joshua Ferris and many others, almost all of the novelists connected with McSweeney's echo Wallace's interest in metafictional techniques, comic observations, wordplay and stories that go round and round and round. Most famous among them is Foer, a writer whose novels seem to offer the most striking expression of the possibilities and the pitfalls of the kind of project mapped out by Wallace. Both of Foer's novels offer sparkling demonstrations of technical sophistication at the same time as they expose an alarming intellectual naivety. Everything is Illuminated (2002), a novel that seems, in various awkward moments, to pre-empt Borat (2006), finds itself torn between its commitment to linguistic virtuosity and its attempt to represent the Holocaust. In similar terms, Extremely Loud and Incredibly Close (2005), his gauche account of 9/11, offers a dramatic illustration of the gulf between a politically limited and sentimental tale and an endlessly inventive telling.

While prefiguring key parts of Foer's narrative architecture, Infinite Jest is, in contrast, a less arch, less mannered novel. Wisely perhaps, it does not engage with real historical events, but prefers to offer a satirical pseudohistory of the near future, and as such it is able to step cheerfully past the traps that Foer finds so easily. It is, moreover, a novel that glows with an avuncular warmth that makes it, like all of Wallace's work, enjoyably readable, a quality that needs to be interpreted in part as a reaction to the flat minimalism that dominated much of American fiction in the 1980s and 1990s. When Wallace started writing, Raymond Carver's voice was dominant, notably on the creative-writing programmes run at many US universities. At the same time, blank tales of urban angst in the brand-heavy world of New York and Los Angeles were becoming the novels of choice for many American readers. Wallace clearly felt ill at ease with these hard, laconic styles and was particularly critical of Bret Easton Ellis. “If the contemporary condition is hopelessly shitty, insipid, materialistic, emotionally retarded, sadomasochistic and stupid,” Wallace observed,

In this respect, his love of playful language, rambling plots and easy compassion can be read as a reaction to the studied bleakness of a novel like American Psycho (1991). Unlike Ellis, the world Wallace imagined was never mean and shallow and his vision, though often pessimistic, was rarely cynical. In keeping with the work of the best writers in the McSweeney's stable, or indeed in the cinema, where similar energies are informing the films of Charlie Kaufman, Michel Gondry and Spike Jonze, there remains, despite all of the difficulties raised by his revamped metafiction, Wallace's determination to find life in goofy stories. His richly complicated linguistic games are consistently endearing.

Reading Wallace's witty, loquacious fiction in these terms, does, inevitably, prompt unhappier reflections on Wallace himself and the nature of his death. Suicide encourages reappraisal and just as it is hard to read Sylvia Plath or Virginia Woolf without thinking about the way they ended their lives, so too is it difficult not to look for intimations and evidence in Wallace's work. At first sight, Wallace, an author with limitless intellectual energy and good humour, seems an unlikely victim of his own despair. The sad truth is, however, that the clues were everywhere. Though well disguised by linguistic riffs and the endless narrative twists, there is no doubt that the mental turmoil of the Incandenza brothers, all three mourning a father who took his own life, forms the spine of Infinite Jest. Even so, the novel looks a lot gloomier today than it ever did before. When I first read it over one long hot summer at the end of the 1990s, I heard echoes of merry pranksterism in the title. Today it seems to resonate much more deeply with a grim Shakespearian nihilism.

True of his fiction, it is also true of his essays. Though many of them, like “Up Simba,” a memorable piece on John McCain's first attempt to secure the Republican Party's presidential nomination, are beautifully comic, there is, in reality, a persistent strain of melancholia in all of Wallace's work, a strain that seems even more sorrowful when it surfaces in unlikely places. “How Tracy Austin Broke My Heart,” for example, is an essay in which Wallace sets out to entertain his readers (and himself) in characteristic fashion by aiming some weighty literary cannonballs at the soft target that is the tennis star's ghostwritten autobiography. At root, though, his engaging overreaction to the crowd of banalities that fill Beyond Center Court: My Story (1992) is actually motivated by a much more mournful conceit. For Wallace, himself a highly ranked junior tennis player, Austin's book is initially fascinating because it seems to reveal an astonishing absence of self-consciousness. Her ghosted persona is uniformly sunny, aware only of life's positives even as she faces up to the events that will end her career. Wallace is struck that she is unable to think of a single critical observation to make about her fellow players, the parents that had her playing tennis from dawn till dusk six days a week, or the injuries and misfortunes that saw her slip from world number one at eighteen to virtual retirement at twenty-two. For him, at least at the start of his essay, her lack of insight is astonishing.

As the piece comes to its conclusion, however, it becomes increasingly clear that Wallace is starting to envy her lack of imagination, starting to envy her ability to shut out the clamour of doubts and insecurities. In the end, it is this that really breaks his heart. Unlike Austin, he could never shut out “the Iago-like voice of the self.”Footnote ⁶ As James Wallace explained to the obituarist from The New York Times, his son had “been in hospital a couple of times over the summer and had undergone electro-convulsive therapy. Everything had been tried, and he just couldn't stand it anymore.”Footnote ⁷