Howard Jacobson (L) and Paul Holdengräber (R).(LivefromtheNYPL/Flickr)

Paul Holdengräber, who has the enviable job of interviewing extremely interesting people for the New York Public Library’s discussion series, wore a fedora and no tie Friday night, while his interlocutor, Howard Jacobson, who became the first Jewish man to win the Man Booker Prize last year (though, as he noted, Jewish women have taken home Britain’s most prestigious literary award), wore a dark suit and red tie. The clothes belied the men. Holdengräber, whose mitteleuropean accent and boyish earnestness make it almost okay for him to say things like “I was perusing my library and happened upon Cicero,” was curious, inquisitive, and arid, while Jacobson—like the characters in his novels—was boisterous, funny, and outrageous. He was also very, very obviously Jewish, in contrast to Holdengräber, about whom it was a genuine shock to hear that he, too, was a Member of the Tribe.

Yet in many ways they represented the two archetypes of the Jewish intellectual (Ashkenazic, anyway). For what is Jacobson if not the ribald and morbid Jew from the Pale—that goofy mane of hair, those capital-b Bushy eyebrows, and that gigantic nose!—the fragility of whose life has led him to fear harm and to raise humor as a shield. And Holdengräber reminded you of the staid German Jew, even-keeled, cerebral, always a step removed from the messiness and flesh and thingness of day-to-day life. Here was Holdengräber citing Verlaine, Rimbaud, and Baudelaire, ostentatiously articulating the names in impeccable French, the way Alex Trebek does; and there was Jacobson mocking this continental finnickiness. It was not ten minutes into the 90-minute conversation before Holdengräber had quoted Freud, that prototypical German Jew: “Happiness is a belated fulfillment of a prehistoric wish.” But for Jacobson, all gratification is immediate.

Holdengräber had solicited a seven-word biography from his guest, and Jacobson duly provided, “Novelist, critic, humorist, tragedian, raconteur, wit, controversialist.” But Jacobson immediately objected to his self-definition: “I didn’t know it was going to be announced that I had said them.” And anyway, perhaps his foremost adjective is “English”: The man who told Tablet Magazine that he prefers not to be called the “English Philip Roth”—as he frequently is—but rather the “Jewish Jane Austen” insisted, again, that he was “an Eng. Lit man.” “There were boys who were obsessed with American literature,” he remembered of his schooling days, “and I thought they were a bit sharp.” The best novel ever written, he said, is Great Expectations, and it’s also the best novel ever written about sex.

“I feel a desperate need to argue for comedy, in novels,” Jacobson said, “ because I don’t like novels if they’re not funny.” He loves comic digressions—“I do digress. I’m digressing now”—but finds the father of comic digressions in the English novel, Lawrence Sterne (who wrote Tristram Shandy), to be a habitual offender of the unnegotiable ban on unfunniness. Specifically, he lacks “jocosity. It’s humor that isn’t funny.” And, he added with a mischievous gleam in his eyes, “The non-funny novel, that’s what normally wins the Booker Prize.”

(His narration of what it was like to win the prize was a classic Jewish joke, complete with the mother. Upon finishing the book, she called him and said that while she enjoyed it, “It’s too Jewish.” When he was long- and then shortlisted, she constantly reminded her son not to get his hopes up. On the morning of, she did the same. She pledged not to watch the awards ceremony, which is televised, but in the end had a whole party. This was the same woman who warned him, when he got his acceptance letter from Cambridge, to check the front of the envelope to make sure it was really addressed to him.)

Jacobson can make anything funny, you get the sense. He even made his grouchiness about contemporary technology—”Facebook and Twitter will kill us: We’ll be Twitted to hell!”—funny: “It’s no argument against me that I’m old anymore than it should be an argument against them that they’re young. Except it is!”

Jacobson spoke movingly about a childhood in England where he spent hours in his room listening to sentimental Italian songs he didn’t understand. “I didn’t know what a consumptive whore was, but I sang songs that broke my heart.” Holdengräber had a Neapolitan ditty sung by Mario Lanza cued up to be played, and it was piped in through speakers. Then Jacobson continued: “I longed to be a Neapolitan. These small, round Italian men who were versions of Jewish men. They’re always singing goodbye. ‘Goodbye to Sorrento.’ Where the hell is Sorrento?”

Yes, there was politics, although for Jacobson politics are more a matter of the personal than vice-versa. “Zionism was partly a liberation of the Jews from Jewishness,” he said. “And it upsets me to see Israel becoming religious again.” Though a supporter of the Jewish state, Jacobson is even more proud not to be a citizen: “But we love the diaspora. I like being a diaspora Jew,” he proclaimed. “We love being outcasts. I don’t want to be a Jew among other Jews. It’s a sickness to which I’m wedded.”

As the evening progressed, they got to talking about aging, and old age, and death, and it became clear that the most perfect American analogue to Howard Jacobson is Woody Allen, the man who flings art up against slowly encroaching death. This approach is best mocked in, well, Manhattan, when Diane Keaton’s character reacts to the Woody character’s praise of director Ingmar Bergman with this nice retort: “I mean, all that Kierkegaard, right? Real adolescent, fashionable pessimism. I mean, the silence. God’s silence. OK, OK, OK. I mean, I loved it when I was at Radcliffe, but, all right, you outgrow it.”

Holdengräber had been with Jacobson earlier in the day when he got a chance to hold the pen Dickens used. To some, it would be inspirational; to Jacobson, it was a memento mori, Yorrick’s skull. “He was called The Immortal,” Jacobson remarked of Dickens, sarcastically and bitterly.

“The fact of mortality covers everything, and it’s the other side of laughter,” Jacobson argued. “Comedy is a human invention to deal with the sadness of life. It’s our greatest achievement. Forget the pyramids. Comedy.”

Related: Smash [Tablet Magazine]
The Plot Against England [Tablet Magazine]
The Solipsist [Tablet Magazine]
Earlier: Howard Jacobson Pulls Off Booker Upset