In 2013, Philip Roth said that he had “two great calamities” still to face: “death and biography. Let’s hope the first comes first!”

The first did come first — in 2018, when the great American novelist was 85 — but not before he was able to appoint his biographer. Once Roth had satisfied himself that “a gentile from Oklahoma” was the man to write the life of one of the pillars of the postwar Jewish-American literary tradition, he offered Blake Bailey some advice. It came in the form of a passage from his 1990 novel Deception.

“Philip”, an American writer living in London, imagines the challenges facing the biographer of Nathan Zuckerman, the “real” Philip Roth’s fictive alter-ego who appears in several of his novels, and whose life closely resembles Roth’s own in several particulars — notably, a Jewish upbringing in New Jersey and later notoriety for a scandalous and sexually raucous bestseller (Carnovsky in Zuckerman’s case, Portnoy’s Complaint in Roth’s).

“What interests him,” says “Philip”, “is the terrible ambiguity of the ‘I’.” Roth suggested that would make a good title for the project on which Bailey was about to start work.

Philip Roth, Bailey’s authorised biography, is an exhaustive and deeply sympathetic account of a life that began in the predominantly Jewish Weequahic section of Newark, New Jersey, and ended in a hospital bed not far away in New York; and of a long career that started and finished with prizes (a National Book Award in 1959 and the National Humanities Medal awarded to him by President Obama in 2010) — with a great deal of contention and controversy in between.

Comparing Roth’s work with that of other giants of postwar American literature such as John Updike and Don DeLillo, Bailey declares that it “stands the best chance of enduring”. And although the kindest thing one can say about him as a critic is that he has a flair for concise précis, Bailey does give the reader a vivid sense of the richly varying modes in which Roth operated — from the “sombre realistic novels” he wrote in the early to mid-1960s, through the hectic metafictional explorations of selfhood in his middle period, to the so-called “American trilogy” of American Pastoral, I Married a Communist and The Human Stain, which for many is his greatest achievement of all.

Bailey’s task was not an easy one. He knew, for instance, that Roth had dismissed a biography of Saul Bellow, his friend and literary hero, as full of “righteous, boring pseudo-psychiatric moralizing”. He knew, too, that Roth had warned a previous would-be biographer of his against a reductive preoccupation with his sex life: “It wasn’t just ‘Fucked this one fucked that one fucked this one’.”

The implication of that admonition was that any account of his extravagant philandering ought to be tethered to some larger meaning. But sometimes, surely, “fucking” is just “fucking”, and occasionally the strain of suggesting otherwise shows in Bailey’s book.

Philip Roth with his then wife, the actress Claire Bloom

For instance, when Roth was living in London in the early 1980s, during which time he was in the middle of a 17-year relationship with the English actress Claire Bloom, he became friendly with the playwright David Hare. Bailey tells us he gave Hare the following piece of advice: “Never let her sleep in your bed. Make sure you’re the person who can leave.”

Hare, Bailey assures us, “never perceived such an outlook as misogynistic so much as a matter of ironclad priority: Work comes first, even before sex.”

That’s one way of putting it, I suppose. And it’s how you’d read the episode if, as Bailey does, you believe that one of the “great themes” of Roth’s life (and, for this most productively self-absorbed of novelists, his work) is the struggle of the “I against the They, a longing to live on one’s own terms”. Bailey’s Roth is shaped by having entered adulthood in the early 1950s, what the critic Irving Howe called the “Age of Conformity”, and is forever looking to slough off the bonds of convention.

To his credit, though, Bailey doesn’t stint in recording those occasions on which Roth’s longing to live on his own terms curdled into something more unattractive. A good example is his unhappy final meeting, in 1985, with the novelist Bernard Malamud, a member, along with Roth and Bellow, of the presiding triumvirate of Jewish-American letters, and the model for the writer EI Lonoff in the first of Roth’s Zuckerman novels, 1979’s The Ghost Writer.

Although Malamud was by this time a “frail and very sick old man”, he was still able to muster enough strength to start work on a new novel, some chapters from which he read to Roth, who told Bloom later “that he [had been] compelled to be honest when a fellow writer asked his opinion”.

After Malamud died, Roth wrote a eulogy to him which the writer and critic Alfred Kazin thought was infected with a “bouncy sense of his own success, his constant keeping of the score on other novelists”, especially Jewish ones.

Perhaps, but what success, you can imagine Roth retorting. Even before the succès de scandale of Portnoy’s Complaint in 1969, he was pulling in sums that novelists today could only dream of. In 1967, he was paid an advance of $102,000 for his second novel When She Was Good, regarded today as a minor work in the Rothian canon. The following year, thanks to advances and sales of movie and paperback rights for Portnoy, he made, by his own calculations, $827,000 (more than $6m in 2020 dollars).

There was at least one writer to whom Roth deferred, however, and that was Bellow. Bailey rightly stresses the role that Bellow played in showing Roth new ways of trying to capture the modern Jewish-American experience.

Bellow was the anti-Malamud. In the latter’s “essentially folkloric and didactic” imagination, Roth wrote, “the Jew is innocent, passive, virtuous”. Whereas as in books such as Bellow’s The Adventures of Augie March, other possibilities are glimpsed — a role for the Jewish novel as something more than the vehicle of “ethnic propaganda or comfort”.

Roth first scoped out those possibilities in the late 1950s in the novella Goodbye Columbus and in short stories such as “Eli, the Fanatic” and “Defender of the Faith”. His portrayal of the sly and manipulative army private Sheldon Grossbart in the latter would bring down the opprobrium of official American Jewry on his head.

Letters of complaint flooded into The New Yorker magazine, where it was first published. “Your . . . story makes people . . . forget all the great Jews who have lived,” one correspondent wrote. Others accused him of being an anti-Semite. And the president of the Rabbinical Council of America asked: “What is being done to silence this man?”

1959 is one of the hinge moments in Bailey’s account, and was momentous for Roth for another reason. That year he married Margaret Martinson, whom he’d met three years previously in Chicago. This relationship was a disaster, and they married only after Martinson had feigned pregnancy by buying a jar of urine from a pregnant woman she’d met on Manhattan’s Lower East Side.

Martinson was killed in a car crash in 1968, just around the time Roth was finishing Portnoy’s Complaint. In 1974, after a series of what Bailey describes as “zany, alienating books” that didn’t sell particularly well, Roth published a novel entitled My Life as a Man, in which, as he put it, he sought to turn “the shit of that marriage into a book”.

Reviewing it in The New York Times, writer Anatole Broyard said that Roth seemed “to have a bone to pick with women”, rather than — as Bailey suggests — one woman in particular. Whatever the merits of Broyard’s review, it set a template for the subsequent reception of Roth’s work.

In a 1984 interview, the English academic Hermione Lee asked Roth about the “feminist attack” on his work for its unsympathetic treatment of female characters. “Don’t elevate that by calling it a feminist attack,” Roth replied. “That’s just stupid reading.” Literature, he said, echoing his reading of Malamud, “is not a moral beauty contest.”

It’s a defence to which Roth would return 15 years later during a seminar at Bard College, where his friend Norman Manea had invited him to discuss six of his novels with a group of students. In the final session, devoted to I Married a Communist, the second book in the American trilogy set during the McCarthy era, discussion soon turned to the portrayal of Eve Frame, a proxy for Claire Bloom, by then his ex-wife, who had recently published a highly unflattering memoir of their time together.

“I invented her,” Roth protested. “We don’t have to have easy moralizing reactions to characters in literature.”

Roth later complained to Bellow that the younger generation’s “aesthetic antennae [had] been cut”. Less high-mindedly, he also grumbled that “you used to be able to sleep with the girls in the old days. And now of course it’s impossible. You go to feminist prison. . .”

Eschewing censoriousness, Bailey leaves it to the reader to decide if that’s where Roth belongs.

Philip Roth: The Biography, by Blake Bailey, Jonathan Cape, RRP£30, 898 pages

Jonathan Derbyshire is the FT’s acting deputy world news editor

Join our online book group on Facebook at FT Books Café