I’m not exactly sure how this happened. I’ve been a book nerd all my life, having grown up in a household full of crowded shelves, where the most appropriate Shabbat afternoon ritual was a trip to the library. My grandparents’ homes were full of books by the Major Jewish Writers—Bellow, Malamud, Singer, Roth—but my parents (though they both work in the Jewish world) were less interested in them.

As I got older and started writing about books professionally, Roth’s supremacy was unavoidable: He was always collecting awards, making everyone’s top-10 lists, serving as a reference point for critics talking about sex in literature, Jewish identity, misogyny, and New Jersey—all things I ostensibly cared about. His face regularly peered out from articles in newspapers and magazines, and his unsmiling face with its graying orbit of hair was familiar in a way that made me look past it and on to articles about new writers, whose books were so often positioned as rebuttals or complements to Roth’s legacy.

Not having read any Philip Roth felt alternately reprehensible and like a point of pride. Could I actually appreciate the landscape of contemporary fiction without him? On the other hand, we all have to build our own canons, and everyone’s education has its gaps, intentionally or not. (I knew I couldn’t be alone in this aspect of my under-education; there had to be plenty of well-read people who had their own reasons for having avoided him, too.) And I’ve always been skeptical whenever a author is hailed as the savior of literature, the Great American Novelist, or the embodiment of all we could hope for in a writer—whether that writer is Philip Roth or Jonathan Franzen or Zadie Smith or Roberto Bolaño. Slowly, though, the fact that I didn’t know Roth’s work started to feel like an opportunity, a rare chance to approach something with relatively few preconceptions. Sure, I knew the basics: Roth was prolific, Jewish, aging, cranky, and venerated. But how did his books read? Would I like them?

With his 31st book, Nemesis, arriving this month, catching up on him completely was a daunting and not entirely pleasant prospect. And I didn’t really want to try. After all, if I wanted to fully understand Roth and his intimidating oeuvre, I would read all 31 of those books, along with critical biographies and anthologies and interviews that detailed the experience of reading him from just about every possible perspective, along with Claire Bloom’s scathing memoir of their relationship, Leaving a Doll’s House. I would read through hundreds of reviews and consult the experts at the Philip Roth Society. Instead, I just wanted to find out what it was like to persist on a Philip Roth diet for a few weeks, to see what it would feel like and if it would tell me anything about the way I read. I wanted to know if Roth was a writer it was even possible to get a general sense of, by dipping my toes into a few supposedly exemplary novels. So, I didn’t read 31 books. I read eight.

The way I chose those books was far from scientific, based on casual suggestions and availability as much as the specifics of Roth’s bibliography. His first book, Goodbye, Columbus (1959), was an obvious choice, and as the novel that made him famous (and both exalted and reviled), so was Portnoy’s Complaint (1969). Someone told me they thought I’d like The Counterlife (1986), which seemed as good a tip as any, and I took home The Plot Against America (2004) both because I’d heard great things about it, and because it was already at the library instead of needing to be transferred in. I added Everyman (2006) to my pile for the same reason (and also because it was nice and slim when compared to most of the others, as well as relatively recent), and The Breast (1972) because, well, it’s about a man who turns into a giant boob. I knew I wanted to read American Pastoral (1997) because it won Roth the Pulitzer Prize, and Patrimony (1991) because I figured a memoir would offer a different angle on the author. Skipping around seemed legitimate, since I wasn’t trying to understand Roth’s evolution as a writer in any kind of comprehensive way, but to see what came of ploughing through a stack of his books in a concentrated amount of time.

Even if I wasn’t sure what I would actually find in these hundreds of pages, I knew what I was supposed to find. The promotional copy on many of the books was comically over the top: It seemed like each one was hailed as Roth’s greatest triumph, the one boasting his most indelible characters, the rawest emotion and deepest cultural relevance, and the author glared out from his photo as if daring anyone to contradict the superlatives. The aura of undisputed greatness triggered competing impulses in me: On one hand, it’s reassuring to read books that have already been vetted and generally agreed to be excellent. Another part of me, though, was annoyed that adoring Roth should be a foregone conclusion.

Portnoy’s Complaint, I realized just a few pages in, is a book you really need to immerse yourself in—it should be read in as few sittings as possible. With very few section breaks and a careening narrative (the whole thing is truly a relentless, exhausting complaint), the best strategy is to get into the groove of Alex Portnoy’s voice and let it pull you along. And with little to hang on to in the way of structure, it’s the characters and small stories that stick: Alex’s account of his young cousin’s suicide, his ambivalence about his girlfriend (whose serious sex appeal can’t make up for what he thinks of as her unrepentant stupidity), another cousin who almost married a goy and then died in the war, the horror movie (and indelible, odious archetype) that is his mother. Portnoy’s life is one long, sickening Jewish joke; Roth is trying so hard to repel and frustrate us that reading becomes a sort of test of will.

I knew the book by reputation, of course, but the repulsive, repressive Jewishness at its core was still extreme enough to be jarring. It’s certainly to Roth’s credit that the book still shocks more than 40 years after it was published, especially considering that at a certain point, its literary value became inseparable from its cultural cachet. That’s the challenge of reading a book that’s become shorthand to such an extent that The Daily Show jokingly called it “the Jewish manual” on the same night I finished it. Somehow, though, Portnoy’s Complaint still stands on its own.

After that, reading The Plot Against America was a relatively soothing experience, and something of a stylistic shock. The historically complex novel is impeccably structured and straightforwardly told and makes Portnoy look like a sheer cathartic exercise in comparison. On a basic level, The Plot Against America is just a great read: It’s accessible and vivid and suspenseful along with being a smart, sly history lesson. Reading Roth’s alternative history of the period preceding America’s intervention in World War II and knowing this is not what happened to American Jews in the 1940’s (but could have, given some choice unfortunate events) makes you want to know more about what actually did. Something about tracing the divergence of history and fiction fixes the facts in your head better than the usual accounting of them and made me think the book would be an inspired way to teach anyone from high-school students to forgetful adults about the period. In a different way, Goodbye, Columbus also felt to me like it belonged on a syllabus, so much so that I was hearing reading comprehension questions in my head as I was reading: things like, why does Neil care so much about the kid in the library? Why does he insist that Brenda get a diaphragm? What does the title actually suggest? The Breast was similarly ripe for essay questions. It also just works: It’s short, funny, and disturbing, with the blend of comedy and pathos that defines absurdity.

I found The Counterlife harder to get lost in, though I know that’s part of the point of the book’s structure—its multiple “lives” and shifts in perspective are meant to be disorienting, each chapter set in a new time and place that forces a reader to start from square one each time. That idea appeals to me, as does Roth’s fascination (very much on display in these pages) with calling his readers’ attention to the way a story is constructed. Still, there was just so much speechifying here, so much yelling about who was right and wrong, and the stakes never engaged me.

But I thought American Pastoral, which also had some meta qualities (and which I was similarly primed to think was genius), was staggeringly good. I loved how Roth built the saga of his main character, Swede Levov, out of the memories of his own alter-ego, Nathan Zuckerman, so that Zuckerman’s personal reflections drive nearly the whole first quarter of the book, before the character smoothly shifts his attention to imagining the Swede’s story. In these layers of authorship and invention, it’s not just Roth writing the book, but Zuckerman building it out of his own memories and feelings about the past, fiction upon fiction. There’s a lot going on here—high-school sports, family tensions, political violence, sex, cattle-breeding, embattled optimism, blackmail, urban ruin, the bizarrely fascinating specifics of how to manufacture women’s dress gloves—but the entire book is riveting and deeply sad, revolving around lost dreams and ideals and an underlying question of “why me?” that one might call biblical if it didn’t instead resonate as distinctly, terribly American. It’s that rare novel that kept me reading long past the point when I planned to go to bed, and I haven’t been able to stop thinking about it since.

The day after I finished American Pastoral, I read Patrimony in three hours. Roth’s memoir of his elderly father’s decline was harrowing, lovely, and impossible to put down, its ending inevitable but the exact path to it heartbreakingly uncertain. Lucid and forlorn, he’s writing about the experience of memory here as much as he’s recounting specific ones, and they’re memories that actually belong to him, rather than ones he’s ascribing to his various fictional stand-ins. After reading so much that represented a meeting of his life and fiction, the Roth who is writing here seemed strikingly exposed. There’s nothing sexy or glorified, just shit smeared all over the walls and a son tasked with cleaning up the mess.

This felt like a reasonable, tidy way to conclude my reading spree. But Everyman—the first of Roth’s recent cycle of short novels—was still sitting at the top of the pile next to my coffee table, taunting me with its brevity.

For all its slimness, Everyman struck me as one of the bleakest books I’d ever read. It’s not merely depressing, but insistently, painfully grim. The book is a fairly concise chronicle of an aging man consumed by his mistakes, and it makes growing old sound like the hardest, loneliest, and most desperate situation a person can be in, to the point where it seems to have been written from a place of utter fear and despair. A few of the plot points were drawn directly from the pages of Patrimony: the severe heart trouble Roth recognized just in time to save his life, how he made a wrong turn on the way to visit his father and ended up at the crumbling cemetery where his mother was buried. In Patrimony, Roth writes that while that accidental detour offered him no comfort, it nonetheless left him satisfied because it felt “narratively right.” It was an apt way to describe the broader relationship between his life and work, and it was strangely gratifying to see so clearly how he’d translated that particular experience into fiction—15 years after he described it in a memoir.

Everyman left me so despondent that I worried it would color my feelings about Roth’s other books. But that might have happened had I finished with any of the others, too (albeit with a different aftertaste). And in the end, my Philip Roth binge made it hard for me to think of any one of his books as an individual work. Read together, they left behind a web of allusions and cross-references and authorial obsessions and outbursts and reflections that I’m happy to leave all tangled together in my head, letting the Nathan Zuckerman of American Pastoral touch base with his younger self from The Counterlife, having Swede Levov explain his familial knowledge of glove-making to the nameless protagonist of Everyman (who himself has some expertise in the fine jewelry trade), and letting Alex Portnoy and Goodbye, Columbus’ Neil Klugman swap stories—while all the female romantic interests get together to compare their own notes on this group of tortured Jewish men. Read on a bender like this, the connections between stories and characters and themes all but broadcast themselves, and I got a better sense of the man behind them than I would have had I read American Pastoral by itself, in installments the length of a subway ride.

We read, I think, to confirm things we assumed, as well as to be surprised by what we didn’t know. And timing matters. All of us remember books we’ve read at the wrong point in our lives—too soon, or too late—or in a moment that felt almost overwhelmingly perfect. There are books whose specifics drifted away soon after we finished the last page and others that we think about often, for reasons we don’t always understand. Maybe if I’d read different books by Roth, or the same ones in a different situation, my opinion of them would be less favorable. Maybe if I added just one more book to the stack, I would have gotten too sick of him to have anything positive to say.

Or maybe not. Discovering Philip Roth this way was totally unnatural, but it felt totally right. And, hey—now I’ve read Philip Roth.

A good definition of a major writer, in fact, is that even his bad books matter—if not for themselves, then for what they say about the mind that created them. Nemesis (Houghton Mifflin Harcourt, $26), Roth’s new novel, is a case in point. For the last six years, since the publication of his last great book, The Plot Against America, Roth has been producing short novels at an accelerating pace, but with declining powers. This is quite natural for a writer in his late 70s, and the subject matter of these works—impotence, old age, and death—are equally appropriate to the closing phase of Roth’s career. In the “books by” page at the beginning of Nemesis, we find that he has now grouped four of these recent books together in a new category: Along with the Zuckerman books, Roth books, and Kepesh books, each named after their protagonist/narrator, there is now “Nemeses: Short Novels.”

The new book, then, gives a name to this sequence, which also includes Everyman, Indignation, and The Humbling. As the word “nemeses” suggests, each is about a man brought low, by a combination of his own flaws, bad luck, and the relentlessness of time. But since the protagonist of each book is also a shadow-version of Philip Roth, these stories have a power in excess of their slight fictional achievement. In each case, Roth seems to be imagining an alternative fate for himself, a variation on his own life that ends in failure or disaster, rather than fame and glory. In Indignation, Marcus Messner actually speaks from beyond the grave—he is a young man who, tormented by sexual guilt, drops out of college and gets killed in the Korean War. And in last year’s The Humbling, Simon Axler is an aging actor who loses his self-confidence and virility and is ruined by his attempt to regain them in a last love affair.

Nemesis, the latest installment in this sequence, is also the worst. In part this is because of the thinness of the prose, which has next to nothing of Roth’s grand style—the indignant, self-justifying rant learned from Céline, balanced between laughter and fury. There are sentences in Nemesis that, in their expository limpness and characterlessness, seem to have no authorial mind behind them at all:

Franklin Delano Roosevelt, polio’s most renowned victim, had contracted the disease as a vigorous man of thirty-nine and subsequently had to be supported when he walked and, even then, had to wear heavy steel-and-leather braces from his hips to his feet to enable him to stand. The charitable institution that FDR founded while he was in the White House, the March of Dimes, raised money for research and for financial assistance to the families of the stricken.

The language gives itself away: “renowned,” “vigorous,” “charitable institution,” “the stricken,” are all clichés, and the whole thing sounds like it could come from a history book for young readers. This may be a clue to the problem: Roth seems to be writing for an audience that has never heard of the 1940s—of FDR, polio, or D-Day (later on, we hear about how soldiers “parachute into Nazi-occupied France … against the stiffest German opposition”). Of course, this describes none of the likely readers of Nemesis, and the disconnect suggests that Roth has become too isolated—by age, fame, or habit—to successfully imagine his own audience.

The story, too, has a young-adultish plainness and didacticism. Bucky Cantor, the hero, is a 23-year-old P.E. teacher in the Jewish Weequahic neighborhood of Newark, New Jersey—the setting of Roth’s own childhood, which he has explored in many books. It is the summer of 1944, and Bucky is working as a playground director, running baseball games for the neighborhood kids. And it’s through the kids’ eyes that we see him: Roth chooses to narrate the story in the voice of one of Bucky’s students, despite a good deal of narrative implausibility, because it allows him to halo the young teacher in childish admiration. When Roth writes that “His was the cast-iron, wear-resistant, strikingly bold face of a sturdy young man you could rely on,” you know that, as in a movie, countenance is character.

Bucky’s heroism is tested by an outbreak of polio in Newark, which claims the lives of two boys from his playground. At first, he is as plucky as his name requires, attending the victims’ funerals and comforting their families. Even more important, he tries to stop his neighbors from working themselves into a suspicious panic. At the time, Roth reminds us, it was not known how polio was transmitted, and as in The Plague, ignorance breeds paranoia. Did the dead boys catch the virus at a hot dog stand, or from a slovenly, mentally retarded boy, or from the spit of an Italian gang that trespasses on the Jews’ turf? Bucky keeps insisting that it is wrong to give in to fear, to blame the Other—a familiar moral to a familiar story, which unspools in foursquare Hollywood fashion. There is a tearful eulogy for an angelic child; a kindly, reassuring neighborhood doctor; and even a devoted girl for Bucky—Marcia Steinberg, the doctor’s daughter, who wants nothing more than to marry him.

But it is Marcia who turns out to be the cause of his undoing. She is working at a summer camp for Jewish children, far from the polio outbreak, and she arranges for Bucky to be offered a job there. His sense of duty—heightened by his guilt at being unable to fight in World War II, thanks to his bad eyesight—tells him to stay where the trouble is, even though realistically he can do nothing to stop the children of Weequahic from getting polio. But his love for Marcia and his instinct for self-preservation lead to him to accept the camp job. What ensues is an idyll, which—again as in a movie, a horror movie this time—becomes more frightful the more perfect it appears, since the reader knows that Bucky is not going to be allowed to get away with his transgression, no matter how minor. In the end, he is punished in a terrible fashion, and a coda, set decades later, shows that the events of that summer ended up ruining his entire life.

In only two ways is this story markedly different from a Hollywood melodrama of the period in which it’s set. The first is that, because the epidemic afflicts a Jewish community in 1944, there are faint but very deliberate reminders of the destruction even then being visited on European Jews. These echoes are the more powerful because Roth seldom insists on them. When rumors surface that Weequahic is going to be quarantined, for instance, the description of the plan—“They would close it off at the Irvington line and the Hillside line and then at Hawthorne Avenue and at Elizabeth Avenue. … They even printed a map”—sounds just like the way Jewish quarters were barricaded, for very different purposes, in Vilna and Warsaw. The image of Jews as disease-carriers, too, was central to the Nazi ghettos, and when it surfaces in New Jersey, the result is a historical vertigo like the one Roth created so effectively in The Plot Against America: “The anti-Semites are saying that it’s because they’re Jews that polio spreads there. … Some of them sound as if they think the best way to get rid of the polio epidemic would be to burn down Weequahic with all the Jews in it.”

The subject of Jewish suffering naturally leads to the subject of theodicy. Why, Bucky wonders, did God allow the children of Newark to be decimated? Why did He create the polio virus in the first place? This questioning is pitched at such a rudimentary level that it leaves the reader a little unsettled—surely Roth is not suggesting that taunts like Bucky’s (“Look, your God is not to my liking. … He spends too much time killing children”) are going to strike any reader with the force of a revelation. In the book’s last section, the narrator finally gets the chance to reproach Bucky in the way the reader has been doing silently all along: “this is nothing more than stupid hubris … the hubris of fantastical, childish religious interpretation. We have heard it all before and by now we have heard enough of it, even from someone as profoundly decent as Bucky Cantor.”

But if Roth realizes how melodramatically unoriginal Bucky’s story and Bucky’s thoughts are, why write Nemesis? The answer, as with Roth’s last few books, is simple and moving. He is writing these counter-deaths in order to prepare for his own death; he is writing because writing has been his life, and each new book is an extension and assertion of life. When we do start talking about Roth in the past tense—which may not be for many years—it is in this sympathetic light that, I think, his very late work will be viewed.

Few writers in their mid-60s have the ambition, not to mention the stamina, for the kind of self-reinvention Roth undertook 15 years ago. But late Roth, it turns out, was not the last disguise the shapeshifter would assume. That phase, it is now clear, came to an end in 2004, with the publication of The Plot Against America, the last of Roth’s large, backward-looking novels. The books he has produced since then, as he entered his 70s, can only be called late late Roth—or better still, endgame Roth, since they are a series of meditations on last things. In Everyman and Indignation, Roth’s protagonists are actually dead, looking back on their lives from beyond the grave. In Exit Ghost, his alter ego Nathan Zuckerman is impotent, which for a Rothian hero is a fate worse than death.

Now comes The Humbling, the latest installment in this wan series. The title could have been used for any of those three books, especially Exit Ghost, for Roth is once again dwelling on impotence—in this case, not just sexual but artistic, too. “He’d lost his magic. The impulse was spent,” read the first lines of the book, and they tell us everything we need to know—in fact, just about everything we ever learn—about Simon Axler, Roth’s latest avatar. Just as Saul Bellow used to make his alter egos professors or journalists, but wrote about them as if they were really novelists—that is, as if they were himself—so Roth makes Axler an actor, a calling that can easily be translated back into its writerly original.

Axler, like Roth, is a world-renowned artist entering old age; like Roth (and like E.I. Lonoff, the writer-recluse of The Ghost Writer), he lives in almost total seclusion in a farmhouse in the Berkshires. But Axler has also lost his talent and confidence, which can hardly be said of a novelist who continues to publish a book a year. Or can it? Certainly Roth has not suffered any conspicuous, demoralizing failure, as Axler did when “he was asked to play Prospero and Macbeth at the Kennedy Center—it was hard to think of a more ambitious double bill—and he failed appallingly in both.” This debacle, coming after a series of bad performances, drove Axler from the stage, and even brought on thoughts of suicide. Very early in The Humbling, when Axler’s wife leaves him, he comes so close to pulling the trigger that he checks himself into a mental hospital.

Axler’s artistic humbling may not reflect Roth’s experience. But whatever power and interest The Humbling possesses comes from the reader’s sense that it does reflect Roth’s apprehensions. After all, Roth is too unsparing a writer not to realize that The Humbling, like its predecessors, represents a dramatic shrinking of his fiction’s power and scope. The book is very short—a novella at most—and thinly imagined, with few surprises in plot or language. Roth’s characteristic rant—the vengeful, self-justifying, exhilarating speeches in which his characters define their anger and appetite—has shrunken, here, to Axler’s repetitive querulousness:

What was he doing in this hospital room? A self-travesty had come into being who did not exist before, a self-travesty grounded in nothing, and he was that self-travesty, and how had it happened? Was it purely the passage of time bringing on decay and collapse? Was it a manifestation of aging?

The one element of wildness, of transgressive energy, to be found in The Humbling is, ironically, the most ordinary of all, coming from Philip Roth: sex. The book’s first section, “Into Thin Air,” ends with Axler refusing his agent’s offer of a role in a Eugene O’Neill play. He has come to terms with his loss of talent and, at the standard retirement age of 65, resigns himself to a futureless future. “Something fundamental has vanished. Maybe it had to. Things go,” he ruminates. But the next section is titled “The Transformation,” and it shows Axler suddenly reinvigorated by a challenge even greater than O’Neill.

That challenge is Pegeen Mike Stapleford, a 40-year-old woman he has known since she was born. She is the daughter of two old friends of Axler’s, fellow actors who never made it big; she was named after a character from Playboy of the Western World, in which all three of them were playing when she was born. If the title of the Synge play seems like a prophecy of Axler’s imperial libido, Pegeen Mike’s bisexual name is a symbol of her lesbianism. Yet, in what cannot help reading like a parodically macho Rothian development, no sooner does Pegeen show up at Axler’s house than she falls in love with him and decides to become straight.

“It had been some time since she’d had what she wanted rather than its grotesque inversion,” Roth writes, and Axler goes about inverting her inversion with a complacency that I imagine almost any reader under 40 will find absurd, if not offensive. (“Then he led her to the sofa in the living room, where, blushing furiously as he watched her, she undid her jeans and was with a man for the first time since college.”) Like Jimmy Stewart with Kim Novak in Vertigo, Axler buys Pegeen new clothes and gets her hair cut, making her into the woman of his dreams: “In the New York stores, after trying on something new in the dressing room, she’d come out to where he was waiting for her to show him how it looked and to hear what he thought.”

But if Axler remembered the Hitchcockian parallel, he’d know that this kind of egoism does not go unpunished. “Converting” Pegeen, Roth allows us to see, is the great challenge and gamble of Axler’s late life: if he has the charisma and potency to turn her straight, then he might no longer be the wreck we met in the first pages of the novel. He begins to dream about returning to the stage, and even of having a child. But in the savage sexual warfare of Roth’s world, there is nothing more dangerous for a man than to put so much of his self-worth in a woman’s hands: “Eventually a day will come, Axler thought, when circumstances render her in a much stronger position for it to end, whereas I will have wound up in a weaker position merely from having been too indecisive to cut it off now. And when she is strong and I am weak, the blow that’s dealt will be unbearable.”

The title of the The Humbling leaves no doubt that the blow is coming. We can see an image of Axler’s future in Louise, Pegeen’s last lover, whose jilting has turned her into an obsessive, jealous wreck. And Axler seems to be tempting fate by introducing women—first a fantasy, then a real one—into his lovemaking with Pegeen, in passages that allow Roth to show that his boldness in writing about sex has not deserted him. (By far the most memorable scene in the book involves Pegeen’s green strap-on dildo.)

In The Humbling, as in Exit Ghost, Roth does not indulge his hero’s dreams of being young and potent again: as Philip Larkin wrote, we all know what “the only end of age” must be. It is only this remorselessness that rescues The Humbling from its undoubted limitations; that, and the fascination of watching a writer who has written so well, for so long, negotiate with a certain dignity the equally remorseless humbling of his own gifts.

Adam Kirsch is a contributing editor to Tablet Magazine and the author of Benjamin Disraeli, a biography in the Nextbook Press Jewish Encounters book series.