I met Daniel Genis at a bookstore. It was March, and I was there to speak on a panel about Sergei Dovlatov, the comic novelist of late Soviet decay, and Genis came up to me afterward, wanting to talk about books. Books, it became clear, were something he knew about. Genis talks quickly and often, and his pale, insinuating eyes make him look like he’s in on a really stupendous secret. On that night, he wore a T-shirt pulled snugly over a substantial belly and an ill-fitting blazer. He had a good reason to be at the bookstore: his father is Alexander Genis, a collaborator of Dovlatov’s who happens to be one of the best-known nonfiction writers working in Russian; a collection of his essays is currently on Russia’s best-seller list. The younger Genis and I talked. It came out that our parents knew each other slightly, and we had gone to the same high school, and after a while I wondered out loud why we hadn’t met. The reason, he confided, was that some weeks earlier he had been released from prison, where he spent ten years and three months after pleading guilty to five charges of armed robbery. He also remarked, offhandedly, that his authentic education as a reader began not while he was a history major at N.Y.U. or working at a literary agency in Manhattan but at the Green Haven Correctional Facility, in Stormville, New York. There, he offered, he had read a thousand and forty-six books.

We stayed in touch, and, in the course of several dinners and many bottles of sulfurous mineral water from Brighton Beach, Genis filled in more details. He grew up in Washington Heights, in an apartment that, in the eighties and early nineties, doubled as a clubhouse for hard-drinking Soviet émigré writers and artists. His father—a cultural critic, essayist, and radio host whose place in Russian letters can be suggested by some unlikely melding of Bernard-Henri Lévy and Bill Bryson—presided over the steady flow of guests and vodka. With Dovlatov and the journalist Petr Vail, Alexander Genis edited the influential Russian-language weekly “The New American.” At the apartment on Ellwood Street, the men cooked and discussed art and politics and downed many toasts, and it often fell to the women—usually Genis’s wife, Irina, who worked for Pan Am—to clean up after them. Some visitors imbibed so heavily that the following morning they woke in the tub; a plastered Dovlatov once presented a five-year-old Daniel Genis with an air pistol. Genis fils sported a suit and earned allowance from his father in exchange for completing difficult books and translations in Russian. “As a young child, I was treated like a miniature adult,” he told me. “And I learned from an early age that as long as you were talented and artistically successful, your every transgression was forgiven.”

Genis’s social life in high school centered on the downtown punk scene and the music of the Wu Tang Clan, but in private he haunted antiquarian bookshops, combing the stacks for eighteenth- and nineteenth-century editions of Greek and Roman classics as well as Aquinas, Montesquieu, and Dante. By junior year, other books inspired him to dabble in drugs, and surround himself with those who took them. “Devouring Nietzsche, Burroughs, and the Beats was probably not the brightest idea for a teen-ager,” he remarked. In college, Genis began to buy cocaine from street dealers he knew in Washington Heights and resell it to fellow N.Y.U. students at downtown prices. The profits paid for more books, a semester in Copenhagen, travel around Europe, and a large rental on the corner of Second Street and Second Avenue, where, in 1999, he sold an ounce of cocaine to an undercover police officer. It was his first offense, and a lawyer managed to plea-bargain the charge down to a C felony and five years of probation, probably owing to what Genis summarizes as “white privilege and my youth.”

Genis hated having to ask his mother to post bail, but he wasn’t unduly concerned about his career prospects. “I always knew that I would work with books, and book people didn’t seem too concerned about past drug offenses,” he said. While in college, Genis interned with the publisher Applause Books, where he wrangled an editing credit on a film encyclopedia, and after graduating from N.Y.U.—a semester early and cum laude—he went to work for Nancy Love, a literary agent on the Upper East Side. He handled contracts and the slush pile. By the time he lost that job, two years later, a girlfriend had introduced him to injecting heroin. He discovered that he had become addicted while visiting Latvia with an uncle; he copped at the Riga train station, where the dealer offered to let him use a communal Soviet-era syringe that he carried in his coat. Back in New York, Genis married a Hungarian party promoter named Petra Szabo; for nearly a year after the wedding he managed to keep his habit a secret from her. He underwent detox and rehab, and even tried methadone, without success. The habit was costing him more than a hundred dollars a day and he was constantly broke. In 2003, while earning twenty-five dollars an hour as an S.A.T.-prep instructor with the Princeton Review, Genis owed five thousand dollars to a downtown heroin dealer, a Ukrainian with a violent reputation. “I became scared, especially for my wife,” he said. “In hindsight, I should have asked my parents to lend me the money.”

Instead, Genis embarked on a string of robberies that must rank as some of the most hapless in the city’s annals of crime. In August of that year, in the course of a week, he held up two stores and three pedestrians with a pocketknife, apologizing at length before running away. “I was just a terrible thief,” he told me. Two men foiled Genis’s attempt to mug them by throwing a pizza at him. One irate store owner—a petite woman who was shuttering a tea shop for the night—replied to his demand for money by demanding that he “get the fuck out.” Genis complied. By the week’s end, he had stolen enough to pay the dealer, and then finally managed to stamp out his addiction. He was clean for three months when a woman whom he had robbed spotted him on the street. Genis was handcuffed on the corner of Stanton and Bowery. An item about the arrest in the New York Post was headlined “‘Sorry Bandit’ Jailed in Polite Rob Spree.” Genis was still on probation, no one posted bail, and he spent the nine months prior to sentencing at Riker’s Island. In June, 2004, a judge gave him twelve years, ten of them mandatory.

Genis has lived in a dozen maximum- and medium-security prisons, a ringside seat to the pageant of the American penal system. While incarcerated, he clerked for a rabbi, took up bodybuilding (only to injure his back), witnessed a race riot and a murder, watched a man attempt to drown himself in a toilet, and ate a seagull prepared by a prison gourmet. He got to know Michael Alig, the “club-kid killer”; Robert Chambers, the “preppie killer”; and Ronald DeFeo, Jr., who murdered four siblings and his parents and inspired the novel “The Amityville Horror.” Mostly, though, Genis read. “Days in prison have a sameness to them, and my most meaningful and frequent conversations were with authors,” he said. He kept track of the books in a journal. Recently, he allowed me to peruse a stack of loose, mismatched pages crammed with his small, neat handwriting. Each book is numbered and described in entries that are essayistic yet succinct, a form Genis attributes to the uncertain supply of writing paper in prison. He finished the last book on the list—a memoir by Alig, which he liked—in January.

“I started out with books that helped me make sense of the situation around me,” Genis recalled, meaning books on imprisonment: he read “Papillon,” Dostoyevsky's “The House of the Dead,” Gulag narratives by Solzhenitsyn and Shalamov, “The Autobiography of Malcolm X,” Albert Speer’s memoir of Spandau, and Ted Conover’s “Newjack: Guarding Sing Sing” (four pages of which were removed by prison authorities). Then he boned up on authoritarian regimes (“Awful stuff that made me feel better by comparison”): biographies of Pol Pot, Mao, and Pinochet; histories of the Khmer Rouge and the Cultural Revolution; and Goebbels’s diaries. Having entered prison as an atheist with a moral-relativist bent, Genis next took up the problem of good and evil, scouring Pascal, Rousseau, Schopenhauer, “Crime and Punishment,” and Knut Hamsun’s “Hunger.” Lubricated with an ample dose of science fiction by William Gibson, Frederik Pohl, and Philip K. Dick—“for relaxation”—Genis’s journal was just getting going.