Sam Lipsyte is a master of erudite, equal-opportunity loathing, a desolating humor populated by characters blighted by the world. Home Land -- his last novel -- was one of the funniest books of the last two decades. It was so raucously good, many will think that any follow-up is destined to fail. But The Ask's precarious position between total success and not living up to expectations is a result of Lipsyte's expanding vision -- from Home Land's small-scale intimacies to the end of the financial world as many have known it. The terrible massiveness of this vision has to be confused and strange and just as miserable as it is funny because the failure of Lipsyte's Western world is epic and unstoppable.
The Ask features Milo Burke, a development officer for the arts program at a "mediocre" New York university. Burke's caustic wit fuels hilariously profane and misogynist office banter with his jaded co-worker Horace, but his self-hatred (he wished to be a painter, his unfaithful wife is "all touched out," he's got a 3-year-old son who thinks he's a "pansy") and class resentment (just one element in his cornucopia of socio-political rage) make him horrendous at his job. While his colleagues bring in gifts of "endowed chairs, editing suites, sculpture gardens," Burke offends the Jewish ancestry of his last "ask" and fails to get a meager collection of plasma TVs.
Milo is a glutton for punishment, and the book opens with one of the only moments where he actually reacts to being mistreated. Fired for snapping at the entitled art-student-daughter of that potential TV donor, he has been left without work, health insurance for his family, and purpose.When his former boss contacts him unexpectedly and offers him his job back on the condition of a particular ask, Milo jumps at the offer even though he hates the job. The target of the ask, Purdy Stuart, was a rich kid who Milo partied with in college but whose family wealth split their post-graduation paths, a frenemy "who had powers of cajolement, a gentle quasi-Christ-y authority." Purdy purports to want to donate to the university on behalf of his wife, but he admits to Milo that his giving is really about covering up the fact of his illegitimate son. Milo reacts to the moral dilemma that Purdy's proposition thrusts upon him by surfing the web, ruminating on "how sick and marvelous an age this was" where anyone could be "a Newton, a Diderot."
But no matter how Milo tries to ignore his problems, he can't escape his life. The bottom can drop out of any of Lipsyte's moments: "All was peachy and near utopic until I rose for a beer. At that moment the knowledge just disappeared, tilted out of my earhole." And then Milo begins to whir, riffing away, deeper, more lost: "I'd have to start again, or else concede my memory palace was a panic room. It would be good to exile some items and sensations, some people, even, but how to cull? I could not spare one hamburger or handjob."
From here, The Ask documents Milo's powerlessness in a world where money is the acknowledged measure of love, status, family, compassion, and art, even as the book's seams stretch taut and almost break. Instead of slowing the narrative to face some of the cultural volatilities The Ask sets in motion, Lipsyte gives us too much of Milo's navel-gazing. And so what should be an astonishing climax (a scene in which Milo expresses sincere love and worry for his son) is only a flash of bright light in the darkness of a looming alley as the book races toward closure.
These missteps in pacing are nearly erased by Lipsyte's genius and dexterity. The Ask is alive with lexical cartwheels, laced with the jittery eroticism of pornographic fantasies: "I had already begun to picture my cock in high quiver, sliding up the lubed swell of her chest. We were in a library of lacquered wood. Viola tones rose from a carved alcove. Baby oil beaded on rare folios." Lipsyte's imagination is profane in the best and worst of ways; the few times his rocket-fueled prose fails to be funny it reads like overly scripted slapstick or bad standup. There's more pain and dread than in his previous novels, but Lipsyte once again delivers whipsmart dialogue and slightly cartoonish protagonists, men and women whose inflated oddities act like blinking neon signs. All of his characters are catastrophes.
But what is most remarkable about The Ask is how Lipsyte has grown and enlarged his target. In doing so, he has found another way to make us grin wildly at someone's refusal to succeed. In fact, he can be so comical that the laughter that Lipsyte elicits sometimes allows us to forget that he's one of our best documentarians of the crumbling myth of the American Dream.--Alex Lemon
Alex Lemon is the author of Happy: A Memoir and three poetry collections, most recently, Fancy Beasts.
Sam Lipsyte's third novel, The Ask, is a dark and jaded beastthe sort of book that, if it were an animal, would be a lumbering, hairy, cryptozoological ape-man with a near-crippling case of elephantiasis. That's not to say The Ask isn't well hewn, funny or sophisticated, because in fact it's all three…Lipsyte is one of a handful of living American satirists…who can tell a traditional story while remaining foul-mouthed and dirty enough to occupy the literary vanguard. This stuff wouldn't play well at, say, meetings of the D.A.R.too bad in a way, because it might not hurt them to hear it. Lipsyte is not only a smooth sentence-maker, he's also a gifted critic of power.
The New York Times
Generally, novels make us turn the pages because we want to know what happens next. But with Sam Lipsyte's The Ask, we turn the pages because we want to know what's going to happen in the next sentence. Here rants become arias, and vulgarity sheer poetry. Lipsyte's masters aren't Messrs. Strunk and White; they're gallows-humored Celine, Hunter S. Thompson at his most gonzo, the great Stanley Elkin. Although The Ask is unquestionably funny, it's by no means essentially comic. Its theme, after all, is loss, often heartbreaking loss…In the end, the dazzle simply highlights the darkness and the despair.
The Washington Post
Milo Burke is a trademark Lipsyte creation—a sad sack, sure, but a sweet guy, observant, acerbic, and very winning. A failed painter now working a dead-end job in the fund-raising department of a New York university, Milo is assigned to approach his charismatic and very wealthy college buddy, Purdy Stuart, for a big donation. Things aren't too serene on the domestic front either, and listeners can expect mordant musings on family and fatherhood, lust and the vapidity of office life, and a brutal sendup of academia. And the narration is a revelation: Lipsyte is cool and relaxed and transitions smoothly between monologue and dialogue. There are no strained characterizations—just subtle shifts that indicate a change in speaker—and as Milo, Lipsyte sounds just right—sullen, searching, and prone to sentimentality and sarcasm. Smart, compulsive listening. A Farrar, Straus & Giroux hardcover (Reviews, Oct. 5). (Mar.)
Lipsyte's third novel, a darkly humorous story of sons and fathers, is both his most realistic and convulsively hilarious to date . . . Lipsyte's razor-sharp eye filets dying America, throwing off brilliant riffs and exhilaratingly steep dives from frontal lobe to perineum, sauced with yummy dollops of white liberal guilt . . . Yet for all his wit, Lipsyte's narrator is not above it all but deeply, messily down in it: the casual miracles of parenthood, the deepening thrum of mortality, the grim perdurance of a shaky marriage, 'warm with that feeling of wanting a feeling that maybe had already fled.' Seriously funny, Lipsyte sits alongside such illustrious Daves as Gates, Eggers, and Foster Wallace on the self-conscious shelf, but with a heartfelt brilliance all his own. (starred review)
Lipsyte's new novel, following his cult hit, Home Land, is narrated by another of the author's trademark middle-aged losers: Milo Burke, a development officer at a mediocre college in New York City. Burke's assignment is to reel in Purdy Stuart, a fabulously wealthy tycoon who went to school with Burke 20 years ago. In development jargon, Purdy is "The Ask," and this is Burke's last chance to secure a major "Give" before the global financial system collapses. Lipsyte is a comedian with a rant for every facet of city life. As in Home Land, the recurring topics are failure in America and the failure of America. How did we become the bitches of the First World? The humor is a hipster mix of pop and high culture, but the incessant joking eventually overwhelms the story line. VERDICT A treasure trove of brilliant asides and one-liners, this never really comes together as a coherent novel. Still, Lipsyte's fans will be looking for it.—Edward B. St. John, Loyola Law Sch. Lib., Los Angeles
Another savage, hilarious black comedy from Lipsyte (Home Land, 2004, etc.). Now in his early 40s, Milo Burke has given up his youthful dream of art-world stardom for a sad but steady gig as a development officer at a second-rate university in New York City. But then the spoiled daughter of a fat-cat donor demands a favor, he resists, and she-this young woman doesn't know much, but she does know the score-points out that he is "actually the bitch of this particular exchange." Milo's reply contains "nothing an arrogant, talentless, daddy-damaged waif wants to hear about herself," and he gets canned. To help make ends meet for his (possibly wayward) wife and young son, he takes odd jobs, including a brief and memorable stint as assistant deck-builder to a man whose cherished big idea is a show that features celebrity chefs cooking last meals for the condemned on Death Row. Then he gets a mysterious reprieve from a major potential donor-an "ask," in development parlance-who specifically requests that the university detail Milo to court him and his money. But what will it cost to get his old job back? Before long Milo finds himself serving as a queasy mix of factotum, bagman, client state and sounding board to his old college buddy Purdy Stuart, who assigns him the task of delivering hush money to Purdy's secret illegitimate son, a legless and spectacularly embittered Iraq War veteran. Once again, Lipsyte creates a main character whose lacerating, hyper-eloquent wit is directed both outward at the world-sardonic commentary on parenthood, class privilege, sexuality, the working world, education, ideas of Americanness and much more-and inward; Milo spares himself no degradation, noself-loathing, nothing. As it goes on one can't help noticing, beneath the fevered playfulness, a deeply earnest moral vision akin to that of Joseph Heller or Stanley Elkin. The author's most ambitious work yet-a brilliant and scabrously entertaining riff on contemporary America.