Early on in Gary Shteyngart’s first novel, The Russian Debutante’s Handbook, which celebrated its 10th anniversary this year, the fickle protagonist, Vladimir Girshkin, a 25-year-old employee at the fictional Emma Lazarus Immigrant Absorption Society in New York, has gone to Westchester to receive his perennial guilt trip and a free meal from his parents. Vladimir’s mother has become a moderately successful businesswoman in the U.S. after the family’s departure from their native Leningrad, the city from which Mr. Shteyngart himself emigrated when he was 7. When Vladimir attempts escape to catch the 4:51 train back to the city, his mother, drunk on rum, detains him and makes him pace the house’s master bedroom.
“You walk like a Jew,” she tells him. “I’ve been keeping my eyes on you for years, but it just hit me today, your little Jew-walk. Come here, I’ll teach you to walk like a normal person.” Vladimir braces himself for a long afternoon.
It’s the kind of banal suffering Mr. Shteyngart inflicts on his characters again and again. It’s also a stand-in for the judgmental eye the author casts on the world around him, from the sweeping gesture to the most banal of imperfections. In a broad sense, The Russian Debutante’s Handbook mocks the misguided idealism of the Clinton era, but just beneath the fast-money schemes and comfortably superficial upper middle class lifestyle, there’s a looming feeling of foreboding that a novelistic critique of the happy late-capitalist bourgeoisie is as futile as an intoxicated mother trying to change her son’s lifelong habits over the course of a few hours. (Mr. Shteyngart’s fiction is never too far from the border of self-deprecation.) Mr. Shteyngart has managed to make himself into contemporary literature’s resident crank, and the heir apparent of Philip Roth, with a small—just three novels, so far—but consistent body of work that is neurotic, funny, lascivious and, in spite of its acute cynicism, sincere. He makes a convincing argument that everything is, in fact, not okay. He is one of those rare living writers beloved by both readers and critics.
Last Tuesday evening, in front of an audience of about 100 people, Mr. Shteyngart was sitting in a child-size wooden chair on stage at the Brooklyn Academy of Music, wearing a crooked bow tie and a wrinkled tuxedo. There was a sturdy five o’clock shadow on his cheeks and, resting at his feet, a plastic bag brimming with prescription pill bottles—mostly anti-anxiety and depression meds—and a small flask of Georgi vodka, from which he took the occasional pull. The author, so good at dishing it out in his fiction, now had to take it. He was being roasted.
Edmund White mocked Mr. Shteyngart’s prolific book blurbing, offering some imagined blurbs the author might think up in the future. (Mein Kampf: “This debut memoir by Adolf Hitler has taken the leader of the master race to literary excellence and proves that left to their own devices, blondes really do have more fun.”) It was soon revealed that Mr. White, along with other members of the roasting panel—which included writer and radio host Kurt Andersen, writer Sloane Crosley and New Yorker fiction editor Deborah Treisman—had not read The Russian Debutante’s Handbook until they were obliged to do so by the roast. (“One of my best friends, ladies and gentleman,” Mr. Shteyngart said, gesturing to Mr. White.)
“I’m sure the women in the audience, and the men, have been in shock since the moment Gary took the stage, wondering if it’s possible to be as hairy and as ill-groomed as Gary Shteyngart,” said Wesley Stace, known better as John Wesley Harding, who was the night’s host and one of only a few contemporary authors who has not received a book blurb from Mr. Shteyngart. Ms. Crosley characterized Mr. Shteyngart’s nipples as “like buttons on a fur coat.”
“What has Gary taught you?” Mr. Stace asked her.
“Basically nothing,” she responded.
Mr. Shteyngart used to hug the pedestal of the Lenin statue situated outside his family’s apartment building in St. Petersburg, then known as Leningrad. The Shteyngarts left in 1979, were in Rome for a few months while their applications were processed, then landed in Kew Gardens, Queens.
“Kind of a letdown after Rome,” Mr. Shteyngart said over lunch at Pakistan Tea House in Tribeca on the day before the roast. Still, America was overwhelming. He’d look at highway overpasses and think the cars were flying through the air. “There’s a movie called Moscow on the Hudson that came out around this time, that had a great scene with Robin Williams playing a Soviet immigrant, and he walks into a grocery store and there’s just an aisle of coffee. He goes, ‘Coffee, coffee, coffee, coffee’ and then faints. Too much. That’s kind of what it was like.”
His parents weren’t religious, but he was sent to Hebrew school, where he was made fun of for his furry Russian hat and goggle-like glasses. (“It only lasted eight years,” he sighed. He still wears wide-rimmed glasses, and his face would look young if not for the perpetual stubble.) He joined his fellow nerds at Stuyvesant—“the Math and Science High School” in The Russian Debutante’s Handbook—and then attended Oberlin College, in Ohio, called simply “the Midwestern College” in the first novel.
“You grow up in a Marxist society,” he said, scooping up some cauliflower, “then Hebrew school, which is the opposite of that, then this hyper-capitalist meritocracy—Stuyvesant—and then back to the Marxist society. It’s an amazing loop. All these years, I was hiding being an immigrant. In Hebrew school, I pretended I was German because I didn’t want to be Russian. At Oberlin it was like, ‘Shit, I’m a big fat immigrant!’”
In his senior year of college, he began writing The Russian Debutante’s Handbook, which in conversation he refers to only as “Russian Handjob” or sometimes simply “The Handjob.” The book starts out as a fine selection in the canon of literature about a disaffected young man trying to cope with the Jewish diaspora—Vladimir Girshkin, with his hyper-modern girlfriend, old-world parents and hopeless day job, resembles something like Asa Leventhal reared on a steady diet of straight-to-video porn and high-grade cannabis. But the novel takes a Shteyngardian turn for the ridiculous of the sort that has appeared in all of his fiction: looking to make a little money (so that his girlfriend won’t leave him), Vladimir is contracted to impersonate the feckless son of a Catalan drug cartel at a college interview in Miami. In a hotel room, after they drink several bottles of expensive champagne, the crime boss attempts to rape Vladimir, who fights back and breaks away. With a hit ordered on him, he retreats, like many disillusioned Americans, to Prava—“the Paris of the 90s,” a vaguely fictionalized Prague—where, by nature of his own embittered youth, he becomes the brains of a Russian mafia operation run by a gangster nicknamed The Groundhog. It’s a coming-of-age novel, with the stakes raised to the level of actual survival.
He submitted 30 pages of the book as his application to Hunter College’s MFA program. Chang-rae Lee, the former head of the department, sent them to his editor, Cindy Spiegel, then at Riverhead. Two weeks later, Mr. Shteyngart had a book deal.
“It was the first book of its kind,” Ms. Spiegel told The Observer in a telephone interview. “It was an anti-immigrant story, yet he understood the culture he was writing from. He could tell a new story and he told it in the best way.”
Mr. Shteyngart wasn’t planning on publishing a book. It was something he’d write and rewrite for his enjoyment at his day job—he claims to have been “the worst paralegal ever” at a civil rights law firm—and during his too-long lunch breaks at the Pakistan Tea House around the corner, after which he’d come back “burping lentils” and napping in the deposition lounge. The book was far from a fluke, though. He lived in Italy after its publication, where he wrote Absurdistan (2006), about Misha Vainberg, an obese immigrant from Leningrad with Anorexia Nervosa who finds himself stuck back in his former home after his father kills an American businessman. In his quest to find a visa, Misha ends up in a troubled country called Absurdsvani and finds himself at the center of a collapsing government. Meanwhile, over in New York, Jerry Shteynfarb, author of The Russian Arriviste’s Handjob, has shacked up with Misha’s girlfriend.