At a get-together of college friends in the late 1960s, a decade after we had graduated and were already married with young families, the most literary member of our group insisted on reading us aloud something that he had just discovered. We much preferred to go on eating and talking, but he overrode our objections, and once he began to read, we were laughing so hard that we begged him to stop — so that we could catch our breath.

The author was Philip Roth, and the work was soon to appear as a chapter of Portnoy’s Complaint. Our friend was right: This work was meant to be performed. We were then in the great age of American Jewish comedy, with comedians for every taste — Mort Sahl and Tom Lehrer, Sid Caesar and Mel Brooks, Jackie Mason, Joan Rivers, and Danny Kaye. In those years, about three-quarters of American comedy was fueled by Jews. Mike Nichols and Elaine May were already national celebrities, and Lenny Bruce was being tried on charges of obscenity. Portnoy rode the crest of that wave, topping the verbal exuberance of Groucho Marx and pushing the depictions of explicit sex much further than Lady Chatterley’s Lover and Ulysses, the once-censored books that our boldest teacher had assigned us in college. Roth had broken the boundaries between lowbrow and highbrow culture and turned Jewish stand-up comedy into literature.

I usually choose to write about works of lasting importance — works I like so much that I want to share them with others. Revisiting Portnoy is a little different. Here, I’m interested in why a work that felt so fresh in its time now feels troubling in ways that did not occur to us then. Humor is bound to lose some of its bite once its references need explaining, and popular taste can sometimes shift enough to make us question what we once admired. The changed status of this book has a lot to do with what has since happened to this country’s culture, and with the newly precarious standing of its Jews. It is hard to imagine a gathering of Jews convulsed with laughter over this book today.

As everyone came to know, Roth’s novel comprises Alex Portnoy’s six sessions with his psychoanalyst, a certain Doctor Spielvogel whose German-accented voice we hear only after the book is done. Hilarious that a 30-some-year-old would lie on the couch, pouring his guts out to someone as silent as a cigar-store Indian. Like stand-up comedy, psychoanalysis was also a mostly Jewish profession, and Roth ingeniously blends one into the other.

Freud had written poignantly about the importance of joking as a means of coping with the painful demands of civilization: “What these jokes whisper may be said aloud: that the wishes and desires of men have a right to make themselves acceptable alongside of exacting and ruthless morality.” Portnoy might have taken that for his motto; he is using humor to free himself from the neurosis brought on by the repressive moralism of his Jewish family and culture. Freud considered joking the safety valve that allowed “men” (he was thinking of Jewish men) to continue being upright and moral. Roth might have thought that he was doing the same when he set out to write this book.

Like the classic bildungsroman, this novel follows the hero’s development — through free association rather than chronologically — from childhood to maturity, or what should have been maturity. The opening monologue introduces us to Sophie Portnoy, “The Most Unforgettable Character I’ve Ever Met” — its title borrowed from a then-popular feature of Reader’s Digest. Sophie is the Jocasta to her son’s Oedipus in the psychological formation called the Oedipus complex that Freud identified as a universal condition of males, sometimes described as “being in love with one and hating the other part of the parental pair.” Alex Portnoy considers himself a comic twist of that Freudian disorder, the only son of a Jewish mother all of whose passions and ambitions are centered on him. He is inhibited by suffocating mother love from becoming a proper man, and by his bourgeois parents from developing a normal happy sexuality.

Look, am I exaggerating to think it’s practically miraculous that I’m ambulatory? The hysteria and superstition! The watch-its and be-carefuls! You mustn’t do this, you can’t do that — hold it! don’t! you’re breaking an important law! What law? Whose law? They might as well have had plates in their lips and rings through their noses and painted themselves blue for all the human sense they made! Oh, and the milchiks and flaishiks besides, all those meshuggeneh rules and regulations on top of their own private craziness!

Portnoy breaks all the rules of decorum and grammar, railing against the “restrictions” as though he were being raised in the Haredi community of Monsey rather than by nominally affiliated parents in Newark. When he asks “Am I exaggerating?” he knows he is inflating the American Jewish stereotypes. The Sixties were the years of shedding inhibitions, and when the Hombres sang “Let It All Hang Out,” Roth exuberantly took up the charge to write what one critic called “the dirtiest book” ever published. Take that, you meshuggeneh keepers of the kosher laws!

Although the sexual content of this book got all the attention, inviting questions about Roth’s misogyny, the anti-Christian zingers aim deeper, as if he were releasing payback that had been stored up against the Gentiles for two millennia.

From the second session, “Whacking Off,” which describes adolescence as “half my waking life spent locked behind the bathroom door,” the book veers into the lower depths. Jewish parents, the epitome of bourgeois morality, instill in the boy habits of responsibility and proper social behavior at the stage of hormonal development when his instincts are profoundly asocial or antisocial. In the rest of the book, Alex relates how the kid masquerading as a good Jewish son gets to “put the id back in Yid and the oy back in goy.” (It really was a funny book.) The goy comes into it because once Alex begins to chase skirts, he is after Gentile women — an added taboo. The id is governed by the pleasure principle, and Alex feels that Jews have gone too far in repressing some of the sexual impulses they consider evil. But since all this is being spilled out by a man in the modern confessional who is seeking absolution through psychoanalysis, and since this patient is employed as assistant commissioner for the City of New York Commission on Human Opportunity, Roth makes it clear that Portnoy never altogether deactivated his Jewish superego. He may have stood among the Jews at Sinai after all.

Back when this book was published, the sexual ribaldry that brought it notoriety genuinely alarmed members of the older generation such as Marie Syrkin, a liberal Zionist intellectual who compared Portnoy to the caricatures of Nazi master propagandist Joseph Goebbels: “In both views the Jewish male is not drawn to a particular girl who is gentile, but by a gentile ‘background’ which he must violate sexually.” Gershom Scholem, the most famous of the German-Jewish intelligentsia in Jerusalem, said that antisemites had always tried to prove the degeneracy of the Jews, and along comes a brash young Jew who does their work for them. “Here in the center of Roth’s revolting book…stands the loathsome figure whom the anti-Semites have conjured up in their imagination and portrayed in their literature, and a Jewish author, a highly gifted if perverted artist, offers all the slogans which for them are priceless.” He wondered “what price the world Jewish community was going to pay for this book.”

These European-born Jews knew the dangerous outcome of cartooning that cast the Jew as corrupter. They could not grasp that Philip Roth was writing this book as the freest Diaspora Jew who had ever taken pen to paper, reveling in the liberation of language and libido. He was not merely following Freud in trying to rid the human animal of its neurosis but expecting to reap huge rewards for advertising all the sexual acts and fantasies that had once been concealed. As Roth explained it, Portnoy’s obscenity was part of his attempt to be saved: “An odd, maybe even mad, way to go about seeking personal salvation; but, nonetheless, the investigation of this passion and of the combat that it precipitates with his conscience, is what’s at the center of the novel.” Roth had mastered the art of making sin pay dividends by playing lewd sexual confessions as therapeutic comedy.

His timing was perfect. It was because he was not living in Germany, because Goebbels and his family had been driven to suicide, and because American culture was becoming so pagan that he felt no longer bound by taboos, whether personal or public. Syrkin and Scholem had no comparable experience of trust in Gentile society and could not imagine such freedom. But then, just try imagining Roth publishing this a little later in his career, say, during the #MeToo movement. Which of the two would have been coming after him first today — the feminists or the antisemites?

Had Jews continued to feel at home in America, Portnoy’s Complaint might have become a once-hilarious literary landmark that had lost its explosive power. Instead, attitudes toward free expression, humor, sex, and the Jews have changed so dramatically that even quoting from it has become uncomfortable. How about this excerpt from the scene where a sexually eager Alex goes to the home of Bubbles Girardi, who is known to be “easy”? 

Tacked above the Girardi sink is a picture of Jesus Christ floating up to Heaven in a pink nightgown. How disgusting can human beings be! The Jews I despise for their narrow mindedness, their self-righteousness, the incredible bizarre sense that these cave men who are my parents and relatives have somehow gotten of their superiority — but when it comes to tawdriness and cheapness, to beliefs that would shame even a gorilla, you simply cannot top the goyim. What kind of base and brainless schmucks are these people to worship somebody who, number one, never existed, and number two, if he did, looking as he does in that picture, was without a doubt the Pansy of Palestine.

What trigger warning should we issue to Christians before that “potentially disturbing content”? Humor may be a protected outlet for aggression, but not even in Yiddish, their internal language, would European Jews have allowed themselves such fun at Gentile expense. Although the sexual content of this book got all the attention, inviting questions about Roth’s misogyny, the anti-Christian zingers aim deeper, as if he were releasing payback that had been stored up against the Gentiles for two millennia. The word “goyim,” which is etymologically neutral to designate the nations among whom Jews have always lived, becomes for Roth almost what “kike” was for the anti-Jews.

Portnoy’s Complaint is not quite the wildly comic experience it seemed to us at that first hearing. Now that comedy has become more suspect than predatory sex, we discover warnings not fully recognized at the time.

So the book is not quite the wildly comic experience it seemed to us at that first hearing. Now that comedy has become more suspect than predatory sex, we discover warnings not fully recognized at the time. Alongside the reflexive satire of Jewish mothers were rough takeoffs of non-Jews, all of which culminated in doubts about the therapeutic promise itself. Alex makes the point with increasing intensity that he is the unhealthy part of the Jewish condition, aware of his disorder and seeking a cure he suspects he will never find.

Doctor Spielvogel, this is my life, my only life, and I’m living it in the middle of a Jewish joke! I am the son in the Jewish joke — Only it ain’t no joke! Please, who crippled us like this? Who made us so morbid and hysterical and weak? . . . Doctor, what do you call this sickness that I have? Is this the Jewish suffering I used to hear so much about? Is this what has come down to me from the pogroms and the persecution? From the mockery and abuse bestowed by the goyim over these two thousand lovely years? . . . Doctor, I can’t stand any more being frightened like this over nothing! Bless me with manhood! Make me brave! Make me strong! Make me whole!

Philip Roth was onto something important that Freud had ignored when he analyzed joking as a creative means of restoring psychological balance. What if there is too much reliance on joking, and the cure proves worse than the disease? Laughter may be an excellent way of coping with anxiety, and is it not wonderful that a quarter century after Treblinka, Maidanek, and Auschwitz, the American branch of a decimated people should have become the national champions of comedy? But Roth identified a streak of hysteria in all that laughter and a heavy dose of pathology in letting it all hang out. Portnoy feared that he was spinning out of control, not just a beneficiary of the Sixties but a casualty of its unhinged freedom.

In the final session of this book, called “In Exile,” our American Jew heads for Israel, looking to be healed. Aboard his El Al flight, Alex recalls the warm Sunday mornings near his home where 20 neighborhood Jewish men, briefly sprung from their familial and economic responsibilities, played their weekly game of softball.

Not boys, you see, but men. Belly! Muscle! Forearms black with hair! Bald domes! And then the voices they have on them — cannons you can hear go off from our front stoop a block away. I imagine vocal cords inside them thick as clotheslines! Lungs the size of zeppelins! Nobody has to tell them to stop mumbling and speak up, never!

That little boy wanted only to live out his life like one of those men right there in New Jersey. “Why leave, why go, when there is everything here that I will ever want?” Those Jewish family men once defined for him what it meant to be a man, yet instead there he is, escaping to Israel from yet another sexual liaison that has gone wrong. He may be hoping to recover in the Jewish homeland the healthy sense of manhood he associates with those Jewish fathers of his childhood.

Portnoy dutifully tours the country, and being the immature, undereducated American Jew that he is, he has pretty trite reactions, like, Wow! Everyone here is Jewish! But far from putting him at ease, familiarity becomes his undoing. He is once again his mother’s Oedipal son, obsessed with proving his manhood in forbidden ways. If every Jewish woman is really his mother, it is no wonder that he finds himself impotent when he tries to seduce an IDF lieutenant he meets on the beach. “Doctor: I couldn’t get it up in the State of Israel! How’s that for symbolism, bubi?” His final downfall comes with Naomi, a post-army 21-year-old nearly six feet tall who “gave the impression that she was still growing,” and with coloring so similar to his mother’s that “this might have been my sister.” First, she parries his advances with a lecture on the corruptions of the Diaspora, and when he tries to tackle her by force, she calls him “Pig!” and kicks him “just below the heart.”

At this last stage of his analysis, the secular Jewish analog to Catholic confession, Alex veers into a rant that ends in an extended scream. And then:

“So [said the doctor]. Now vee may perhaps to begin. Yes?”

Roth presents this one-liner in a separate section with its own chapter heading, as if telling us that we are expected to treat this whole book as a running joke. But self-mockery has taken down the mocker, and no one wants to see the comedian crawling away on his knees.

The joke turned out to be on us readers who thought it was a joke. It is easy to see the influence of this book on the classic Woody Allen film Annie Hall, which develops the same story of the neurotic Jew chasing down the delectable shiksa. But whereas Allen tried to get movie audiences to love his character, Philip Roth was competing with Kafka. Portnoy is not meant to be loved or pitied but approached with a stick like the creature in Metamorphosis, hoping that it does not venture too close. Like Kafka, he did not think he could ever live up to becoming the bourgeois Jewish father whom he tried to escape.

When we laughed at Portnoy (marveling at the writing), we did not think of him as sick. Now that we see what has come of that age of comedy, we read it and weep. Well, not quite, but read (or reread) it and see for yourself.