There's always been more than a whiff of the rabbinical about Howard Jacobson: the beard, the moroseness, the hunched shoulders, the uneasy air of doom. But in this, his grand Jewish oeuvre, he goes further. Not content with interpreting the Bible he's actually set out to write a new Book. A Lamentation, if you like. A Revelation. A Genesis and an Exodus. What he's actually produced, though, is more of a Megillah – that ancient Hebraic text which, for its long-windedness and wordiness, has become a commonplace Jewish term for any story told with insufficient editing: "Don't make a Megillah out of it." "Don't tell me the whole Megillah."

The novel sets out to explain why the Jews are like they are: why they are victims, why they suffer, and why they can't escape. But it really didn't need to be this long, this repetitive, this relentless. Though doubtless Jacobson would shrug in retort that that's the way we Jews are. We just don't know when to let go.

Kalooki Nights is the first person confessional of Max Gluckman – a cartoonist devoted to depicting the persecution of the Jews. Some of his works are so savage that no one will touch them. Like his proposal for a series: Ways of Saying Kosher When You're Not Jewish. "A veritable challenge to the caricaturist and the historian. How would Luther have said the word? How would Haman? How would Hitler?"

Maxie's childhood companion Mannie Washinsky, raised in an ultra-orthodox home in their Manchester suburb and suffused with an encyclopaedic knowledge of Nazi atrocities, grows up to commit an unthinkable crime. What led to and from this most unholy of acts is, for the puzzled, embittered, alienated caricaturist, a parable of all that defines what it is to be Jewish.

And the answer to that question is very simple. It's the Holocaust. "We're Jews because Jewishness is what's been done to us," declaims Max's father. "It's a religion of victimhood."

Or, as Max himself puts it, echoing an earlier literary stereotype: "So we are an immoderate, overemphatic people, much given to exaggeration – so what? I call it giving value for money myself. You prick us so we bleed profusely. You put us to the torch and we burn well for you. Just don't pretend that we invent the conflagrations that consume us."

Max's most cherished work, much of it conceived in childhood with his friend Mannie in their bomb shelter hideaway, is a cartoon account of Five Thousand Years of Bitterness. Each wave of the Jews' oppressors – the Inquisitors, the Cossacks, the random priests and fascists and progrom-perpetrators throughout the centuries – is depicted with a Hitler moustache, all except for Hitler himself. His is missing.

The word Jew, Max confides, will forever mean to him the puffing of the trains that carried Jews to the death camps. Jew, Jew, Jew, Jew is the chorus of the novel and anti-Semitism its unvanquished villain.

Perhaps in homage to that much more profound Jewish chronicler Philip Roth, Jacobson has chosen an Oedipal theme for his great Jewish novel. Not Oedipal as in that of a psyche assailed by the effects of an over-dominant mother, but more in the sense that the further you run away from your fate the harder you crash straight into it.

Unlike the redoubtable Sophie Portnoy, Leonora Gluckman is a cardboard cut-out whose only defining characteristics are that she is beautiful and that she dedicates her life to playing Kalooki. But then, all of the female characters are equally two-dimensional, in keeping with the novel's underlying misogyny. Women are presented as the fate that awaits Jewish men, whether they're running from their roots, denying them or embracing them.

Max's father is a committed atheist dedicated to overcoming the shtetl connotations of Jewishness through devout secularism. And yet – he marries a Jew, his friends are all Jews, the more he kicks against ritual the more it lies in wait for him. He wants only for his children to continue the line away from their poor Russian ghetto ancestry and marry out. The result is that Max, fleeing from his heritage, becomes addicted to goyishe girls with Germanic names and marries two rabid anti-Semites in a row.

Struck by the logic of giving Jews numbers rather than names in the concentration camps, since all Jews look alike, his first wife Chloe thinks it fitting to call him Jew 13. Even the palms of her hands, Maxie explains, are anti-Semitic: "A vexed criss-cross of Judeophobia like the railway tracks going in and out of Auschwitz and... no fingerprints."

How many Jews can you get into a Volkswagen Beetle? quips his second wife, Zoe. The answer? "One thousand and four. Two in the front, two in the back, and one thousand in the ashtray."

The biggest shikseh of all, though, is Ilse Koch, the Bitch of Buchenwold, symbol of Nazi terror and the ultimate castrator of Jewish men. Ilse is the scourge of the Jews personified while Chloe, Zoe and the rest are her signifiers. Which is why the pale, weird, Hassidic Washinkskys must mourn as dead their elder son who runs off with a shikseh. To them, to marry out is a betrayal – and all goyim will in the end turn on you.

"Marry a Christian," observes Max, "and you marry into your own denial." But in Max's iconography there's an even worse enemy – the Jews who turn on other Jews. They're the ones listed in his second cartoon account of Jew-hatred, No Bloody Wonder. Among them are the traitors catalogued by his obsessive friend Errol Tobias whose specialty is knowing the original Jewish names of celebrities. But also included are people like the Washinksys, "who harmed Judaism by being overzealously Jewish where Jewishness had no business showing its face." And then there are those other apostates who seek to deny not merely the fact of Jewishness but its very right to exist.

Max's nemesis turns out not to be the blonde anti-Semites after all. His third wife is Jewish but identifies with the Palestinians in their struggle and is therefore, in his terms, a Jew-hater. The token presence of Israel, the unforgivably simplistic dismissal of this most complex of conflicts, is one of the chief faultlines of this flawed polemic. Max simply equates Israel with the Jews and its enemies as yet more Nazis in disguise.

With its limited vision and bleak nihilism, Kalooki Nights ultimately drowns in its own symbolism, weighted down by a cast of avenging angels, sacrificial lambs and unexpected saviours. But it's worth persisting if only for Jacobson's luscious mastery of words, his dazzling linguistic swoops and dives. Take, for example, his description of Mannie's elder brother Asher. "Where Asher walked, the whole of the Old Testament walked with him. Seeded like a pomegranate he was with the sorrows and the tribulations of his people, but juicy with the wine of the pomengranate, too, spicy with spikenard and saffron, calamus and cimmanon, his lips like a thread of scarlet."

The novel's aim is noble – to relive the horrors of the Holocaust lest it be forgotten. And it certainly succeeds as a diatribe against those who seek to trivialise or deny it. But like the work of its protagonist, it never quite rises above the level of the comic strip, however dark the subject. The characters are too much like ciphers, the bitterness too palpable. Like Woody Allen's irritating fans in Stardust Memories, I can't help preferring the earlier, funnier works.