There's probably not a living American writer who has so comprehensively mined the comic possibilities of that particular anguished, hapless combination of the overeducated and the underachieving as Sam Lipsyte. Against all odds, his heroes refuse to succeed, and they and we are rewarded with the endlessly entertaining spectacle of their nonstop humiliation.
The Ask features Milo Burke—leave it to Lipsyte to hybridize Joseph Heller's monster of systematized selfishness with the eighteenth-century humanist—of "the House of Wanker," whose life hasn't panned out, by which I mean he's both spectator and spear carrier in the theater of his own economic and spiritual collapse. Milo's a fund-raiser for the arts program at a third-tier institution he calls "the Mediocre University at New York City." While his colleagues have delivered endowed chairs or editing suites or sculpture gardens, his last big ask—asks denoting either likely donors or what his school wants from them—failed to land even a few promised plasma TVs. Barely hanging on, Milo is a hiring mistake "bobbing along on the energy tides of others." He particularly despises the obliviousness of the overindulged student body he's working to support, partly because he, too, "had once been a fraud, chockablock with self-regard." When insulted by one donor's undergraduate daughter, he responds with "nothing an arrogant, talentless, daddy-damaged waif wants to hear about herself," and his career is over.
Until, that is, it's resuscitated by the news that his ex-employer wants to go global and link to other mediocre universities worldwide: It seems that to do so they need an old friend of his, who made more money out of his father's money and is ready to throw some around. In graduate art school, Purdy was the Most Likely to Succeed, and that's turned out to be true, in a ghastly and parodic way: No one in Milo and Purdy's peer group has sold out with such success. Even so, Milo's more than needy enough to require Purdy's approval and crave his admiration. So he's a little ambivalent about the sucking up and shaking down he has to do to remain employed. To make things worse, Purdy wants him to serve as a one-man containment unit for his illegitimate son, just back, maimed, from the Iraq war and breathtakingly angry at the world in general and his father in particular. And Purdy's past, the evidence suggests, might even have tipped from the merely sordid to the monstrous. Is Milo going to keep such a revelation under his hat?
Milo's no more up to the challenge than any of Lipsyte's other protagonists would be. See, for example, the hero of his first novel, The Subject Steve (2001), who seems to be undone mostly by boredom. Milo's default during difficult times is collapse. When it comes to ethics, the spirit is willing and hyperarticulate, but as for the rest, he's "an idiot savant without the savant part," and he's had a rocky enough history that his "memory palace [is] a panic room." Every so often, he resolves to change, but mostly he takes self-pity "to new and astonishing heights."
Milo's world disappoints him even more, though, and happily for us, he's the scourge of the upwardly mobile everywhere. Lipsyte provides him with firebombing rants about everything from alternative day cares ("They had a smug ideological tinge about them, a minor Red Brigades vibe") to perhaps that fattest of sitting ducks: the self-importance of the hypereducated (his art school classmate won the student prize "for shitting on a Rand McNally atlas to interrogate hegemony"). None of this captures the performative brio of Lipsyte's sentences, which exhilarate by providing a sense of just what's possible when it comes to unbridled thought, unbridled meaning not only startlingly associative but transgressive as well. A paternal pessimist, Milo assesses his young son's prospects: "It was hard to imagine the boy completing kindergarten, remarkably easy to picture him in a tangle of fish knives and sailor cock under some rot-soft pier." There's a surreal giddiness to the resourcefulness of the perversity here, in the face of failure's crushing banality, as if all the mastery unmanageable in life is on display in this secret life: these utterly performative messages in a bottle to the reader.
Milo's failure is not just a joke, because as much as his self-absorption might suggest otherwise, he's not alone or without specific human obligations: Marriage and fatherhood have raised the stakes. Parenting has amounted to "being helplessly present for the ongoing thwarting of a child's heart," and his wife is alienated enough to have announced herself as "all touched out." For all the pride he takes in his Harry Lime version of misanthropy, Milo's most cherished belief about himself is that he cares too much, that he wants only to recapture that "desperate, emboldening quest for love." Yet he's a veteran of the sort of epiphanies others might call personal growth, and he knows how low-rent and sentimental his "Good Self" can be. The real reason Milo and his loved ones will never understand one another is "because of the minor obligation involved" in relationships. He's not only victim but also victimizer, because some part of him would love the whip hand. In his own bollixed-up way, he's become an assassin of feeling. Lipsyte forces us to ponder why Milo's been so afraid to give it his best, as well as where he's going to find either the courage or the compassion to go forward. Without at least one of these he's down to "the whole mirthless dwindle of things," "the crabbed, moneyless exhaustion that stood in for our lives," and just "digging in for the long night of here." While we laugh and learn, Milo's pain turns out to be our gain.
Jim Shepard's latest book is Like You'd Understand Anyway (Knopf, 2007), a collection of stories.