"It’s not the jokes," Eddie Waters tells a group of aspiring comedians in Trevor Griffiths’s classic play Comedians (1975). "It’s not the jokes. It’s what lies behind ’em…. When a joke bases itself upon a distortion…and gives the lie to the truth so as to win a laugh and stay in favor, we’ve moved away from a comic art and into the world of ‘entertainment’ and slick success." From the misogynist, nihilist novels of Michel Houellebecq to randy popcorn films like The Hangover and The Ugly Truth, we have recently seen the flowering of a certain strain of humor: noxious, sexist and juvenile, this type of comedy sets itself up as an antisocial fun-zone free from the censure of political correctness, an unsafe space where guys can finally tell the truth about how things really are instead of mouthing the platitudes of gender equality expected of males in mixed company. Reveling in the unacceptable is confused with genuine humor, then further confused with truth-telling in the face of a supposedly dominant feminized culture. There can be no question of the mass appeal here, an analogue in comedy writing to the Tea Party movement, which panders to whatever percentage of white males feel disenfranchised by Barack Obama and Hillary Clinton. These works provide a solace similar to that proffered by Super Bowl ads like this year’s incendiary spot "Man’s Last Stand," for the Dodge Charger, which recommended the hot rod as the appropriate reward for any man enduring the soul-killing cheerlessness of a heterosexual relationship. "I will say yes when you want me to say yes," the voiceover intones. "I will carry your lip balm," but "I will drive the car I want to drive." Anyone who complains is no fun and no fair.

In Comedians, Eddie Waters offers his students an alternative:

A real comedian—that’s a daring man. He dares to see what his listeners shy away from, fear to express. And what he sees is a sort of truth about people, and about their situation, about what hurts or terrifies them, about what’s hard, above all, about what they want. A joke relieves the tension, says the unsayable, any joke pretty well. But a true joke, a comedian’s joke, has to do more than release tension, it has to liberate the will and the desire, it has to change the situation.

Many of our best contemporary comic writers seem to have intuited Waters’s lesson. From television shows like The Office and HBO’s Eastbound & Down to the stories of George Saunders, Junot Díaz and David Foster Wallace, these writers, like their less able peers, use male narcissism as the foil for their jokes. Yet these writers are neither chauvinists nor nihilists; their depiction of men being men can be vicious, but it is never static or canned. Saunders, Díaz and Wallace are celebrated not only because they broach the unsayable but also because, despite their eagerness to transgress, their work is fundamentally humane.

Sam Lipsyte’s fiction oscillates between these comic modes. In the four books he has published in the past decade, readers have witnessed an ongoing war in Lipsyte’s comedy between empathy and nastiness. He has skewered the afflictions and affectations of his male protagonists to devastating effect, but he is sometimes unable to generate the escape velocity required to see a world beyond his narrators’ self-absorption. Home Land (2004) was a decisive victory for empathy, and for Lipsyte’s artistry. His latest novel, The Ask, feels disordered and inchoate by comparison. It’s a retreat by a nonpareil comic stylist into the pure but flat art of the vile.

Lipsyte published his first book, a small-press short story collection, Venus Drive, in 2000. Its best pieces mix their shocks with a startling pathos, an effect that is similar to one employed by John Cassavetes in the film Faces, in which hilariously madcap human degradation becomes frightening and at times nearly tragic. In Lipsyte’s "Cremains," the narrator inherits his deceased mother’s apartment, where he spends his days playing handyman and confidante to the lonely elderly women in the building. He also inherits his mom’s cancer stash of morphine and finds himself mainlining with a mixture of narcotics and his mother’s ashes. "Is that the morphine, or is that my mother?" he asks. "Something is setting beautiful fires up and down my spine." In the final pages of Venus Drive, the story "Less Tar" ends with this remarkable cri de coeur: "I Love You, I Love You, Let’s Make it Work, I Love You So Much, Let’s Not Ever Ever Quit." It’s understood that the characters in question will almost certainly fail, but their hopes and dreams (or, if one prefers, their necessary illusions) remain an active force in the narrative.

Lipsyte’s first novel, The Subject Steve, about a dot-com ad man diagnosed with a vague but dangerous disease, premiered on September 10, 2001. In the "smoked-glass murk of corporate life" portrayed in the novel, one of the slogans generated by the narrator is the priceless "How Did You Like Tomorrow?" (Venus Drive‘s "My Life, For Promotional Use Only" features the efforts of a design team to create a White Noise–like "totalizing space for commerce and dialogue.") The Subject Steve shares the worst flaw of The Ask—chipboard characters who serve the jokes in an extraordinary series of one-liners, acid-bath sketches and witty set pieces that add up to something less than a novel. Like The Ask, it reads like a short story that has been fattened up to fill a full-size book or, were it expanded further, could be a television sitcom starring a cranky male protagonist. Still, Lipsyte’s ability to generate a densely impacted poetry of despair is remarkable. In The Subject Steve, one character self-defines in a tight narrative arc of four words: "Smack, whiskey, alimony, syph."

Lipsyte’s deservedly lauded follow-up, Home Land, was a carnival ride of pity and terror in epistolary form. Published first in Britain and later imported to the States in paperback, the book comprises a series of outrageously funny and poignant letters sent to a high school bulletin by a nonplussed alum who "did not pan out," Lewis Miner ("aka Teabag"), a depressed and onanistic antihero with a decidedly creepy sexual nostalgia for the chic leg warmers and white tube socks of the Reagan era.

Home Land is a novel of deep and unexpected compassion. In the final chapter, "The Erasing Angel," Miner writes that "once more I stuff my heart into the firing tube of language, loft it into the void." Yes, the novel documents the life of a man who likens the way he feels to "bathing at knifepoint in the phlegm of the dead," and whose pipe dream for a self-help book is titled The Seven Habits of Highly Disappointed People. Yet heartbreak pervades Miner’s darkness—or, if not exactly heartbreak, then at least, as one chapter title has it, "A Sort of Forlorn Smirk." Of his high school principal, Miner writes, "Some of him is made of charm. Even the charmless parts, I believe, were acquired in provinces of real human pain." When an enraged former classmate writes back to Miner after reading his missives to his school newsletter, asking whether he has "ever traveled, ever loved, ever experienced excitement, ever done anything kind for anyone," the answers, behind all of his dodges and sick jokes, are yes, yes, yes and yes. So, asks Miner, "do I qualify as human yet?"

This note of mournful fellow-feeling descends at intervals in The Ask, such as when a minor character reveals that the delusion that keeps him going as an immigrant ("my lie for myself," he calls it) is that "in America, things can be okay." Mostly, however, the novel tries its best to turn the reader off. The Ask‘s assault on our more delicate sensibilities begins with its very first lines, with the grandiose political commentary of Horace, an office temp who declares:=

Our republic’s whoremaster days were through. Whither that frost-nerved, diamond-fanged hustler who’d stormed Normandy, dick-smacked the Soviets, turned out such firm emerging market flesh?

Milo Burke, the novel’s narrator and antihero, counters: "That’s a pretty sexist way to frame a discussion of America’s decline, don’t you think?" This conversation takes place on the job at the development office of a mediocre New York City university. For Milo, it’s "a good shitty job." He wastes his days ("I wasn’t developing") entertaining sexual fantasies about his female supervisor. Having formerly considered himself a painter, Milo is now scaling back on his life’s ambitions after getting married (to Maura) and having a kid (Bernie). Soon into the novel, Milo is dismissed from his post for mocking a female student as an "arrogant, talentless, daddy-damaged waif." Despite his disclaimer that his mother was a second-wave feminist, Milo’s outburst is deemed hate speech.

"You could say I had experienced some technical difficulties," Milo says of his unemployment. Here he joins a long line of listless Lipsyte protagonists on the outs with their jobs, their love lives and their national culture after brief stints as artists of some kind and subsequent botched attempts to survive in the corporate world. Milo drifts, at one point attempting to join the deck-building business of an acquaintance whose true ambition is to create a reality TV program conjoining the food and true crime genres in a show called Dead Man Dining (condemned prisoners would be fed their last meal by a gourmet chef). Milo spirals downward into a stay-at-home-dad hell involving, among other things, a disastrous attempt to pick up the mother of one of his son’s classmates. Readers of Home Land will note the return of authorial commentary about TV, pop culture, porn and tube socks. Like Home Land‘s Lewis Miner, Milo is intentionally made to look ridiculous. But the universe of The Ask lacks an essential element of Home Land—at the subsentence level, it’s missing something that could be called the charm quark. In this novel, Lipsyte attempts the impossible, a novel that is anti-everything.

As his marriage crumbles—Maura leaves Milo for a graphic designer—the development office of Mediocre University suddenly asks Milo to return. A potential gold-mine donor, Purdy, has requested that his old college chum Milo be his liaison during the process of an "ask"—that is, a proposed large-scale charitable donation, also used as a noun to describe the would-be donor (read: sucker). Purdy is willing to make a massive donation, but he also has personal problems that require Milo’s help. His illegitimate son, Don, is a crazed veteran who has returned from Iraq (and central casting) without his legs. Don regularly sends the daddy who damaged him notes that range from bizarre to extortionate. Purdy wants Milo to act as bagman for Don’s hush money, promising the moon in return for his services. Although Lipsyte’s treatment of combat trauma is severely limited by caricature, the last paragraphs of The Ask contain a final, honest shock about Don that is better left undisclosed, one that obliterates any lingering sense of hope. Why do we expect hope from fiction, or from life? That is what the novel "asks" the reader.

What does a reader ask of a novel? Nobody in the universe proposed by The Ask will grow up, become a fundamentally better person, have a life-changing epiphany, find lasting love or "only connect" in the manner recommended by E.M. Forster. Hackneyed expressions of these tropes deserve our ridicule, but this novel is inordinately unforgiving and cold, especially compared with Home Land. Like almost all of Lipsyte’s work, it depicts hideous men at their most hideous. Its female characters, meanwhile, are designed to play against stereotypes, but this effect is undermined by their lack of depth, psychological or otherwise. Maura is forgotten the moment she leaves the page. The love interests in Lipsyte’s fiction tend to represent missed opportunities or failed attempts to become decent; eventually they decide they’ve had enough of his narrators and move on. Lipsyte intends this as a critique of male narcissism, but it also effectively removes women from the orbit of the story. In The Subject Steve, the ex, Maryse, has a name not very different from Maura, and she goes equally AWOL. In Home Land, the narrator’s fiancée, Gwendolyn, has "decamped." Lipsyte kindles real human emotion in his depiction of Milo’s gay mom, Claudia, a no-nonsense woman self-actualizing after the debacle of her marriage, but she remains peripheral. These aren’t Chekhovian characters with rich interior lives, and, to be fair, that’s not the point. But even in the male-dominated narrative world of David Foster Wallace’s Infinite Jest, the psychological complexity of Joelle Van Dyne (aka "Madame Psychosis") remains vital to the story. Lipsyte never ventures beyond the myopic minds of his eloquently damaged male narrators.

The Ask is meant to be provocative and intentionally unacceptable. Part of the novel’s strategy is to mock the conventions of mainstream literary fiction by displaying overt contempt for the notion of a likable protagonist who, besieged by circumstances, becomes embroiled in conflict, searches for love and meaning, and finally discovers much about himself and the world. Nobody in The Ask is likable except Claudia and the oddly wonderful child, Bernie. But the novel anticipates and deflects this objection. "I’m not very likable, am I?" Milo asks his supervisor. "If I were the protagonist of a book or a movie, it would be hard to like me, to identify with me, right?" "You’re likable enough," says his boss, echoing Barack Obama’s campaign retort to Hillary Clinton. It’s a tactic drawn from the arsenal of metafiction that fails without the firepower of genuine experimentalism; The Ask is, in the end, not a satirical frolic at the expense of narrative structure but a story about what are supposed to be actual human beings.

"What the hell is wrong with me?" asks one of the disaffected narrators in Venus Drive. In Lipsyte’s work, the question is metonymous. What’s wrong with men? What’s the matter with America? In one scene in The Ask, Maura returns home and suggests that she watch a cheesy romantic movie on television while Milo simultaneously masturbates to office-themed Internet pornography at the other end of the couch. The episode auditions as a metaphor for the implosion of their marriage in addition to depicting the definitively disconnected outlets for male and female fantasy in mass culture. Yet the couch episode doesn’t live as fiction because one never learns enough about Maura to understand why she wants this encounter to occur or what it might mean to her. She is, rather, a cipher who stands for the obliteration of the dream of human contact.

The take-it-or-leave-it relish of Lipsyte’s work resides in its diligent refusal to scrub up and play nice. The narrator of "Cremains" keeps a jokey postcard from an ex-girlfriend up on the fridge as "a testament to what’s not really funny." Laughing at what’s not really funny—or, as a corollary, laughing at what’s really not funny—could be Lipsyte’s credo. Dredging up toxic sludge from the bottom of the private or public well, airing the dirty laundry before it is washed and spun—these are some of comedy’s tasks.

The Ask, although often wickedly funny and written in prose of a startling clarity, lacks the empathy of Home Land. Its sorrow is angrier, more depressive and less moving. Lipsyte’s sense of a yearning, failed connection has been smothered by a jaded and implacable misanthropy. The core problem of comic writing is that either the joke serves the characters or the characters serve the joke. What’s missing from The Ask is Home Land‘s human factor, its breaking heart.

It may seem like an old-fashioned question, but it is one worth asking about The Ask: can we, over the course of reading a novel, make do entirely without characters we grow to care for? By the end of The Ask, Milo shows some signs of life—he loses his wife but he still has his son and his painting, which he has demoted, in genuine humility, to the status of hobby. The most honest thing he can say about himself is that he’s "still bitter, was bitter about the bitterness." He’s "digging in for the long night of here."

At its most rigorous, Lipsyte’s work resembles a contemporary basement diatribe version of Notes From Underground; the narrator’s point of view is vivisected, not endorsed. Dostoyevsky’s "sick man" brags about his abominable behavior but cannot fully persuade himself to "become spiteful." It is possible for him to be "genuinely touched," despite all appearances to the contrary. Lipsyte’s successful narrators share this quality, one that is largely missing from Milo Burke.

Is the fundamental problem plaguing The Ask one that Milo would term a "technical difficulty," an all-enveloping first-person narrative that traps the reader inside the suffocating constraints of the very narcissism it mocks? In Home Land, Lipsyte used a similar narrative technique to great effect, finding plenty of emotional breathing room and discovering unexpected poignancy hidden among unpalatable truths. The Ask focuses more exclusively on what’s wrong, both with Milo Burke and with what he calls "dead America." The resulting novel is slight, although its premise—a comedy that rejects fun—is memorable.

David Foster Wallace’s sketches in Brief Interviews With Hideous Men frame their male subjects through a doubly distancing lens: the men’s monologues are fractured by an interviewer, and the title of the book hints at a refreshing assertion of overt sexual politics. These strategies might sound didactic, but they don’t spoil the humor of the book, nor do they blunt the force of the trauma depicted within its stories. It seems possible that a framing device, such as the epistolary format of Home Land or another formal tactic even more outlandish and disjunctive, could have served Lipsyte’s intentions better than the novel-length monologue that is The Ask. In a way, the book is too traditional. The Ask confines readers entirely to Milo Burke’s head, a place that isn’t interesting enough to warrant an extended stay.