In 1969, Philip Roth summoned his parents for lunch in New York City. His novel, Portnoy’s Complaint, was soon to hit bookshelves, and he wanted to prepare them for what he predicted would be an onslaught of controversy and media attention. “You can politely or un-politely hang up,” he said. “They’re just journalists, you know.”

Philip Roth: The Biography
by Blake Bailey
W. W. Norton, 916 pp.

Roth had reason to be worried. He had already been labeled an anti-Semite because his earlier work contained unflattering Jewish American characters. Portnoy was likely to further fuel those charges and was bound to come with another dimension: Readers would unquestionably wonder whether Alexander Portnoy’s domineering and deranged parents were based on the writer’s own. 

After lunch, Roth sent his parents back home to New Jersey. Once the taxi left, his mother began to cry. “What’s wrong?” Philip’s father, Herman, asked her. “He has delusions of grandeur!” she told him.

Of course, Roth’s delusions turned out to be justified. The raunchy and emancipating novel about a guilt-stricken Jewish man’s obsession with sex and masturbation, told in the form of a rant to his psychotherapist, was an immediate best seller and a cultural landmark. Practically overnight, it made Roth into an international celebrity who could no longer dine in restaurants without someone heckling him over whether he was going to order liver (in the most infamous scene, Portnoy masturbates with a piece his family will eat for dinner). 

Twenty-five books later—Roth wrote a total of 31—it remains the one for which he is probably best known.

In reality, Herman and Bess Roth were a devoted and doting set of parents who bore only mild resemblances to Jack and Sophie Portnoy, and Roth’s childhood was very unlike Alexander’s. Roth enjoyed an idyllic upbringing in the Weequahic section of Newark, New Jersey, where he suffered no significant trauma. 

Still, readers were right to wonder. As Blake Bailey observes in Philip Roth, his new, eagerly anticipated, and magisterial biography of the American master, Roth loved to play on the ambiguity. “The most cunning form of disguise,” Roth wrote in The Facts, “is to wear a mask that bears the image of one’s own face.” Many of his protagonists had similarities to the author (some were even named Philip Roth). The author’s rejection of Judaism (“I don’t have a religious bone in my body”) and his adventurous sex life (he was never quite a one-woman man) served as fodder for many of his greatest works, and when not writing about himself, Roth almost always drew on people he knew. He would bring a notebook with him at all times and take notes on what he picked up from interactions with acquaintances. The habit was so pervasive that a lawyer would have to pore through his final drafts to make sure no one could sue him for libel.

Roth’s early depictions of radical individualism made him an astute chronicler of the ethos of the 1950s and ’60s, when young people across the country were railing against authority and the strictures of their parents’ generation. His most pervasive theme was the struggle of the individual against the communal (the I versus the we)—and he always sided with the individual. 

Many of Roth’s characters had similarities to the author. “The most cunning form of disguise,” he wrote in The Facts, “is to wear a mask that bears the image of one’s own face.”

But his rebellious characters, like Portnoy, were flawed and—more than occasionally—a tad perverted. So, too, ultimately, was the individualistic uprising he channeled. By the 1980s, individual rebellion against social authority had morphed into economic libertarianism, which led to the rise of Ronald Reagan and a conservative movement animated by the belief that one should seek autonomy from government. Roth, for his part, was keenly attuned to politics, and later in his career he would offer a prophetic vision of where this ideological crusade would lead. In his dystopian The Plot Against America, written in 2004, Roth imagined what would have happened if Charles Lindbergh had defeated Franklin D. Roosevelt in 1940. In the text, Lindbergh keeps America out of World War II, Nazism triumphs in Europe, and anti-Semitism spreads in the United States. The novel gained new currency when Donald Trump won the presidency in 2016. It was from Lindbergh, after all, that Trump stole his trademark mantra of “America First.” 

Roth’s body of work, however, was hardly focused just on politics or rebellion. His writing touched on an extraordinarily wide variety of subjects, from Jewish American life and the trap of the self to sex and love (and sex without love) and the coming of death and more. What underlay it all was his unflinching commitment to telling the unvarnished truth as he saw it. 

Sometimes, this tendency brought negative attention on himself or his loved ones—as happened with his parents after Portnoy (though it did not impact their relationship; his father, in fact, would offer strangers signed copies of the novel: “From Philip Roth’s father, Herman Roth”). But as Bailey explains, Roth would go wherever his imagination took him, and “the impact on family and friends was something he worried about later, if at all.” As the author once told a young Ian McEwan, who was seeking writerly advice, “You have to write as though your parents are dead.” 

Philip Roth first became interested in literature while earning his bachelor’s degree at Bucknell University. As a sophomore, he started a literary magazine but was barely able to keep up with the mechanics of managing a publication. After getting one of his favorite professors to write an essay on the misuse of the English language, he brought a finished copy of the magazine to the professor, who quickly realized that the paragraphs in his article were arranged out of order. Similarly, Roth’s early experiments with fiction went poorly. By trying too hard to imitate J. D. Salinger, Roth later said, he wrote “very bad, very sensitive stories.”

Roth’s writing talent became clear later, while he was a graduate English student at the University of Chicago and was encouraged to write about the people and places he knew. That led to his first great piece of fiction: his short story “The Conversion of the Jews,” published in The Paris Review in 1958, about a rebellious adolescent who forces his Hebrew school teacher to say he believes in Jesus. From that came other short treasures, such as “Defender of the Faith.” Two years later he wrote Goodbye, Columbus, which won him the National Book Award at the age of 27—the youngest-ever recipient of the prize. 

These works brought Roth literary fame, but they also brought intense criticism. In “Defender of the Faith,” Roth writes about a Jewish soldier who tries to use his religion to get special treatment. As a consequence, Roth was reviled from pulpits nationwide as a self-hating Jew who gave ammunition to anti-Semites. One of the most powerful rabbis in America, Emanuel Rackman, wrote to the Anti-Defamation League, “What is being done to silence this man? Medieval Jews would have known what to do with him.” 

In an exhibition of fortitude, Roth appeared alongside Ralph Ellison for a panel discussion at Yeshiva University in 1963. Making clear that he, as a writer, had no loyalties to his ethnic group, Roth made a more profound point: If writers were forbidden from depicting flawed characters because people with small minds would draw stereotypes from them, then that, in itself, is submission to bigotry. 

Around the same time, Roth made what he would deem his worst mistake: his first marriage. He met Margaret “Maggie” Martinson Williams in Chicago in 1956 and married her three years later, but under dubious conditions. She told him she was pregnant with his child, and despite his misgivings about the relationship—by many indications, Williams was mentally unwell—Roth agreed to marry her as long as she got an abortion. He wanted to first take her to a doctor’s office for a pregnancy test, to which she agreed. Williams then found an obviously pregnant homeless woman and asked her to pee into a cup, which she gave to a nurse claiming it was her own. Never actually pregnant, she then lied about having gotten an abortion. 

Years later, Williams admitted this to Roth. “I was completely stunned on learning of her deception,” he wrote in an affidavit for his divorce case. “Our marriage had been three years of constant nagging and irritation, and now I learned that the marriage itself was based on a grotesque lie.” Their relationship ultimately reached a conclusion in May 1968, when Williams was killed in a car accident. 

But while Roth’s relationship with Maggie caused him an excruciating amount of turmoil, she also provided him with material for his fiction. His 1974 novel My Life as a Man was about a turbulent marriage based on his own; it included the urine episode pretty much exactly as it had happened in real life. On the day he finished the final draft, Bailey writes, he wept in the shower, having “turned the shit of that marriage into a book.”

It was not Roth’s last bad marriage. His second union, with the actress Claire Bloom, from 1990 to 1995, was another source of hardship, humiliation, and, eventually, literary inspiration. Her tell-all 1996 memoir Leaving the Doll’s House was one of the reasons Roth enlisted a biographer in the first place: to set, in his eyes, the record straight. Bloom alleged in the book that Roth was a misogynist and toxic bully who would not let her daughter, Anna Steiger, live with them. According to Bailey, Roth was disturbed by the friction Anna (then in her 30s) brought to their marriage and wrote Bloom a letter asking if Anna could live elsewhere, but he didn’t force her out; in fact, she continued to live with them for six months after he sent the request. That said, Bailey’s account still shows Roth to have been far from a perfect husband: he had multiple affairs during their marriage and could be callously indifferent to Bloom’s needs and struggles. 

Shortly after the release of Doll’s House, Roth checked into a residential treatment center, suffering from suicidal depression. The book created a wound that would haunt him for the rest of his life, the fear that the un-litigated accusations would forever stain his reputation. For that reason, his next novel, I Married a Communist, in 1998, was about a teacher who becomes the target of a McCarthy-era witch hunt, precipitated by an anti-Semitic wife who destroys him.

Despite Roth’s firm commitment from the outset to going wherever his mind took him, his best writing came after both of his parents had died. For all his depictions of characters like himself, who revolt against the expectations of a good Jewish boy, Roth was himself as sensitive and loving toward his parents as one could be.

His most tender book, Patrimony, from 1991, is a memoir of his father dying from a brain tumor. It showcases, perhaps better than anything else Roth wrote, one of his major contradictions: his unmistakable filial piety and his commitment to the integrity of the story, no matter the costs. In the most memorable passage, Roth writes about a time his father, after a biopsy, lost control of his bowels at Roth’s Connecticut home. The son cleans up the shit with a monkish intensity—on the toilet, on the towels, in his hair. Roth gets on his knees and uses a toothbrush to get it out of the crevices between the tiles. Many readers at the time objected to Roth including the embarrassing episode; he had promised his father—in the text!—never to tell anyone. But for Roth, the moment was filled with a kind of spiritual transcendence. It was “one of the most extraordinary and wonderful things that has ever happened to me,” he wrote his friend and rival John Updike. 

The shit-cleaning scene sets up the book’s thesis. Earlier, Roth helps his father set up a will and forgoes his inheritance; he’s a rich man by this point, after all. He advises his father to leave his money to his nephews (the father’s grandsons), who could use it more. Instead, Roth says, he got the experience of washing up for his father. “So that was my patrimony. And not because cleaning it up was symbolic of something else but because it wasn’t, because it was nothing less or more than the lived reality of what it was.” To Roth, the moment is so intensely meaningful because it is stripped of any clichés about what a son “gets” from his father. 

Paradoxically, though, by his making it a seminal scene in his book, it has the opposite effect. As the great Roth critic Mark Schechner once wrote, Roth’s memoir shows how his patrimony was, in fact, “nothing less than his own character: his humor, his stories, his own iron will, vernacular heart, and toughness of mind.” 

Four years later, Roth released his masterpiece, the death-obsessed Sabbath’s Theater, the first novel he wrote from start to finish after both of his parents had died. He was now at his most free to write about grotesque or harsh realities.

Roth would bring a notebook with him at all times and take notes on the actions of his acquaintances. The habit was so pervasive that a lawyer would have to pore through his final drafts to make sure no one could sue him for libel.

An incomparable literary experience, Sabbath moves from the profound to the profane with remarkable fluency, able to at once shock you and disgust you, and then move you. The novel begins with a disgraced former puppeteer and professor, Mickey Sabbath, in his 60s, who regularly masturbates on the grave of his dead lover. The rest follows Sabbath as he plans to commit suicide, with his mother’s voice in his head telling him that it is the proper end to his failed life. Meanwhile, his behavior pushes all boundaries—sexual, social, and moral. It was Roth at his most willing to probe a character who would “let the repellant in,” as he would say, and show no remorse. 

But the book, for all its dirtiness, contains some of the most touching passages of any novel written in the 20th century, such as when Sabbath goes looking for the graves of his grandparents, parents, and brother Morty, who died in World War II, as he reflects on his own looming death. It becomes an elegy for the family members we’ll never speak with again. (It was the passage Roth chose to read aloud when he celebrated his 80th birthday at the Newark Public Library in 2013.) 

More challenging to readers is a haunting passage toward the end, when Sabbath recollects visiting his mistress, Drenka Balich, before she died. (The character was based on one of Roth’s longtime lovers.) Together, they remember, with transcendent wonder, the joy of having once pissed on each other. It is, in a sense, classic Roth—the idea of sex as freedom and transgression, but also of sex as protest. In Sabbath’s Theater, it becomes a protest against mortality itself. 

Drenka’s death leaves Sabbath grief-stricken and feeling ready to die, but what’s noteworthy is that Sabbath lived as Portnoy, a New York City political staffer, wanted to but couldn’t dare allow: in Freudian terms, to fully release the id and abandon the ego or superego. As William Blake wrote, “The road of excess leads to the palace of wisdom.” Maybe not for Roth’s characters, or even Roth the man, but perhaps for Roth the writer. 

Sabbath’s Theater won the National Book Award—37 years after Roth won it for Goodbye, Columbus—and his next three books, his “American Trilogy,” would all earn major prizes, including the Pulitzer for American Pastoral and the PEN/Faulkner Award for The Human Stain.

Toward the end of his career, Roth wrote lesser novels—like The Humbling and Indignation—but he did not lose his ability to tap into, or even anticipate, the zeitgeist. His elegant and final novel, Nemesis, was about the polio epidemic in the 1950s. It depicts the terror of living with the spread of an infectious disease that has paralyzed and tortured a community. All of us, unfortunately, know that phenomenon too well by now. 

It was shocking to many when, in 2012, he announced his retirement from writing. But (unbeknownst to the world at the time) he had been living with coronary heart disease for decades, and he had always disliked the way Saul Bellow churned out weaker work after his mental acuity started ebbing. It didn’t hurt that Roth already had cemented his status as one of the greats, whose name would be in the same category as William Faulkner, Ernest Hemingway, F. Scott Fitzgerald, and Toni Morrison. He would quote the heavyweight champion Joe Louis, “I did the best I could with what I had.” 

And, much as with Louis, no one could question Roth’s commitment to his craft. He was a prisoner to his writing routine and was resolutely dedicated to the cause of literature overall. During the 1970s and ’80s, in one of his greatest acts of service, he engineered the worldwide publication of dissident Czech writers living under totalitarian rule, such as Milan Kundera. 

While he was no longer producing new work, Roth always made the news cycle each autumn when the Nobel Prize winners were set to be announced. It would be a running joke that the Swedish panel would snub America’s greatest living writer every year. “He’s not terribly politically correct, you know, and they are,” said Harold Bloom. By the time they gave the prize for literature to Bob Dylan in 2016, Roth had accepted the injustice. When asked what he thought of it, he said, “It’s okay, but next year I hope Peter, Paul, and Mary get it.” 

Still, he would win every other major literary prize and was highly honored in his final years. In 2011, President Barack Obama gave him a National Humanities Medal. “How many young people learned to think,” Obama said, pausing for dramatic effect, “by reading the exploits of Portnoy and his complaints?”

Note: After this review appeared in the Washington Monthly, W.W. Norton, the book’s publisher, paused sales of the biography while investigating claims of sexual assault leveled against author Blake Bailey.

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Eric Cortellessa, a Washington Monthly contributing editor, is a staff writer for Time magazine.