Mirror, Mirror on the Wall, Who’s the Cleverest of Them All?

Keith Gessen’s great adventure.

Every generation has its clever young men, and Keith Gessen must be counted among them in his. Three years ago he co-founded n+1, a clever yet chasteningly serious little magazine that offers thoughtful articles about such things as the history of the office cubicle and gravely assesses “the intellectual situation” in every issue. Now Gessen has published his first novel, All the Sad Young Literary Men, and it is as clever and self-consciously important and intermittently brilliant as his magazine.

All the Sad Young Literary Men traces the careers of three would-be public intellectuals from their undergraduate or immediately postgraduate years to their early 30s. Self-pitying, self-obsessed, and itchy for recognition, these young men fall in and out of love with the same handful of women, though they themselves are barely acquainted. They shed their outsized ambitions. They acquire new ones. They fail. They become wiser, if not necessarily kinder. Two of them fail spectacularly, defeated by grandiosity, distractability, and the availability of technologies of communication. Sam Mitnick gets a small advance to write the great Zionist epic, though he speaks no Hebrew and has never visited Israel. He spends his days worrying about girlfriends and checking e-mail and falls apart entirely when he discovers that “his Google” (the number of mentions of his name) has gone from from the mid-300s to 22. Mark Grossman, stuck in a graduate program in history in Syracuse, dithers over a dissertation on the Mensheviks, dissects his unsatisfying sex life, and struggles to identify the exact device required by a man afraid to miss the phone call of a woman seemingly destined never to call.

The third young man claims to have failed but has, in fact, succeeded. The novel is proof of that. This character is named Keith Gessen, and he is the only one of the three who gets to tell his story in the first person. He is also, in that now-familiar novelistic hat trick, a creation whose identity mirrors his creator’s in most (though not all) particulars. Like Gessen the author, Keith is the son of overeducated Russian Jewish immigrants, a graduate of Harvard, a resident of Brooklyn, a writer of acclaimed commentary, the brother of a female journalist who has moved back to Russia. Keith likes to regale us with his inadequacies but has a surreptitious flair for survival. At college he toys with, but never quite succumbs to, the two great temptations of college life: drinking too much beer and becoming a Hegel-spouting loser. After Harvard, he gets right down to business, publishing liberal punditry in magazines like the New American and Debate (recognizably the New Republic and Dissent).

Gessen here revisits the world first explored by Claire Messud in her 2006 novel, The Emperor’s Children—that of aspirational intellectuals in the late 1990s and early oughts. Whereas Messud prefers Manhattan dinner parties, Gessen reports from student ghettos and the outer boroughs. His characters, though, are hardly outsiders. One of the pleasures of Gessen’s novel is how well he reproduces the speech patterns of brainy, left-wing Ivy Leaguers—their sardonic deployment of social-theoretical jargon, their riffs on technology and capitalism, their anxiety about status, and the pride in small failures meant to refute their guilty sense of privilege.

The summer after sophomore year, for example, Keith Gessen discovers that all his friends “were going off to make connections and fetch coffee at NASA and the NASDAQ,” while he has made no plans at all. He is forced to go home and get a job moving furniture. He recovers from the setback by confecting cunning paragraphs about his temporary proletarianization: “I abetted gentrification, such as it was; the invisible hand of the market, redistributing the choicest properties as they became more choice and pushing those who couldn’t hack it to the peripheries, was actually my hand, my two strong hands, carrying the antique armchairs of the upwardly mobile and the heavy fold-out couches of those who were falling behind.”

Marginally less pleasurable, but not unenjoyable, is the work the novel forces us to do of separating Keith the character, with his self-congratulatory self-deprecation, from Gessen the author. The difficulty of this exercise explains, in part, both the novel’s comic bite and its faintly bitter aftertaste. Keith charms us with his candor but puts us off with his disturbingly authentic sense of superiority. We chuckle with Keith, but we wonder about Gessen: Are we supposed to laugh with him or gloat with him? At one point Keith admits to having become a regular at the kind of party he first attended in the company of a furious denouncer of phonies named Morris Binkel (identifiable as New Republic senior editor Lee Siegel, a ranter of similar proportions). There he finds women who look at him hungrily, calculatingly, “because like Morris I had won a place among them, among them and above them, and because I had made a mess of my life in the way that Morris, in his time, had made a mess of his.” Gessen is a writer who makes fun of others convincingly and himself less convincingly. For the epigraph of a novel in which his namesake’s acquaintances come off as ridiculous, if endearing, Gessen originally wrote, “To my friends, with apologies.” Then he must have realized how that sounded, because he crossed it out. (The epigraph appears, a line drawn through it, in the uncorrected proofs I was sent for review. I have no business mentioning it. But I thought readers might like to know.)

Don’t let the smug undertone alienate you overmuch, though. Gessen earns it, more or less. He is, in fact, a very good satirist. He skewers with glee, like a latter-day Mary McCarthy. He knows things about today’s young male literary journalists that the rest of us suspect but lack the means to confirm. He knows how overconfident they are and how easily overcome with self-disgust. He knows that they’re starving to be told that they matter and must tamp down the certainty that they don’t. He knows that they’re ferociously career-minded, and terrified of being labeled as such. That Harvardian conviction that one’s every utterance partakes of genius? He grasps that it is more likely to be a trait of men, or at least he does not attribute it to the book’s women. (We don’t occupy the point of view of any female character, which further suggests that he understands his limitations.) Best of all, he knows how his generation riffs. His book is filled with the sort of high nonsense you find in n+1, happily stripped of earnestness. Consider Mark on dating, which,

Mark knew from watching television, was the prime historical movement of his time: it was the biggest industry, the most potent narrative device. It was bigger than sex, bigger than pornography. Dating, builder of cities. And Mark, of course, wanted to be current, wanted to be historical, to participate in the truth regime as it was now constituted: to date, in other words, with maximum anonymity, without the safety nets of parental and social networds, potluck dinners, and work parties. It was the only way to find out, for sure, who Mark was.

Keith’s brush with history is only slightly less absurd than Mark’s. It occurs at the beginning of the novel. Ferdinand, his debauched college roommate, starts bringing Al Gore’s daughter Lauren back to their room. (The timing—this takes place in the mid-1990s—suggests that she stands in for Karenna.) Keith, the suite nerd, flirts with her, has a heart-to-heart with her, dreams of stealing her away from his unworthy friend. He does not. Years later, after the disastrous election of 2000, he runs into daughter and father on Madison Avenue. “She looked happy, flushed, a walking advertisement for our civilization, while her father wore his beard, his infamous beard,” he writes. “I wanted to say to Lauren, ‘I’m sorry,’ though she didn’t look like she needed it, and ‘I wish you were President,’ to her father, who looked like he did.” Gore, however, flinches, and father and daughter rush off.

It helps to know, in deciphering this scene, that Gore is the patron saint of n+1, the Trotsky of Gessen and his post-neoliberal crew. Gore and his beard and his nonpresidency and his thoughts on environmental catastrophe haunt both magazine and novel, reminding us of what could have been and what might be again. By the end of the novel, after Keith has come back from several years in Moscow—”I had grown stronger, my vision was wider, and I saw more clearly than my contemporaries”—and experienced a small personal crisis that some might consider a tragedy and some a blessing, he figures out a whole new way to matter, one that, it would be nice to think, Gore would approve of. “A cabal of liars and hypocrites had stolen the White House, launched a criminal war, bankrupted our treasury and authorized torture in our prisons,” he writes. “And now it was too late—but also, you know, not too late.”

I won’t tell you what Keith thinks will save him and maybe the rest of the America, too, but I will say that as a woman who has been on the other side of the solution he proposes, I don’t think it will. (I’m not sure Gessen does, either.) However, it’s nice to know that the young people (as my 82-year-old father-in-law calls them) still await their glory. It’s their perquisite, and also their job.