I was not alive in the 1950s, but had I been, it is likely I would have thought poorly of the time I was living through—for such was the conventional view among American thought workers, from the academy to the nation’s cultural institutions to its highfalutin media. They told themselves and the country that the decade was an “age of conformity,” during which Americans did as they were told by cultural forces they did not understand. They moved into houses in the suburbs because the culture somehow mandated it, were horribly “other-directed” rather than properly “inner-directed,” and lived in a cultural desert dominated by the “vast wasteland” that was the newest and most powerful mass medium, television.

In the world of business, Americans were all “organization men,” cogs in a gigantic capitalist machine in which even the putatively powerful were all but interchangeable. Hugely popular novels like The Man in the Gray Flannel Suit offered portraits of bland alienation, as men who survived World War II found themselves living a death-in-life within stifling bourgeois boundaries. (This theme would be repurposed to even greater success by Betty Friedan a decade later in The Feminine Mystique.)

It was the socialist sneerer Irving Howe who came up with the phrase “age of conformity” in a 1954
essay in Dissent, claiming that a soul-killing desire to go along to get along was not only predominant in bourgeois America but had infected even the intellectual class. That class had eschewed the bourgeois-loathing world of bohemia wherein all free thought in America had once resided and was now descending into stasis in the form of tiresome but steady academic jobs or profiteering in journalism. “Capitalism in its most recent stage has found an honored place for the intellectuals; and the intellectuals, far from thinking of themselves as a desperate ‘opposition,’ have been enjoying a return to the bosom of the nation,” Howe wrote. “Those feelings of loneliness one finds among so many American intellectuals, feelings of damp dispirited isolation which undercut the ideology of liberal optimism, are partly due to the breakup of bohemia. Where young writers would once face the world together, they now sink into suburbs, country homes, and college towns.”

Looking back, this all seems deranged (and should encourage us all to bring a sense of modesty when analyzing and judging the moment we are living through). What we know about the 1950s with the benefit of hindsight is that it was a time of literally unprecedented prosperity. America possessed something like 60 percent of the manufacturing capacity on the planet Earth, as it was the only one of the great economic powers on earth whose industrial plant was not compromised or destroyed outright by the effects of World War II. Today’s liberals and conservatives alike look back on its particular set of circumstances as a wondrous baseline from which we have declined dramatically. Yuval Levin notes the high degree of social “solidarity” that characterized the decade, as opposed to the almost cartoonish polarization that bedevils us today. Leftists and liberals take rueful note of the unparalleled strength of labor unions, whose negotiating tactics with surprisingly nonconfrontational industrialists helped raise the nation’s physical laborers into the middle class for the first time in any nation’s history.

Americans gave birth in record numbers, a classic sign of a rising and self-confident nation. Abstract American painting became the most important force in the visual arts; the New York City Ballet under the direction of George Balanchine and Jerome Robbins became the most notable dance company on earth; American poets like Robert Lowell, Frank O’Hara, and John Ashbery succeeded British poets in terms of influence; young American writers of fiction from Bellow to Updike to Ellison to Malamud to Roth to O’Connor exploded outward with energetic and profane visions of a country teeming with life.

And, in 1957, a 27-year-old man of the theater made his debut on Broadway as the lyricist of a musical based on Romeo and Juliet. Doubtless the young Stephen Sondheim shared the general disdain for the moment through which he was living; they all did. After all, West Side Story is a portrait of a mid-century New York riven with ethnic conflict and juvenile delinquency, and Sondheim’s lyrics show him scornful even of liberal nostrums about how to cure the social ills of the day (“dear kindly social worker, they tell me get a job…it’s not I’m anti-social, I’m only anti-work…”).

However he felt about 1957 then, nearly a quarter-century later Sondheim would pay beautiful tribute to that year and to the 1950s in general. Near the end of Merrily We Roll Along—a legendary flop notable upon its premiere in 1981 for combining one of the greatest scores ever written for Broadway with a nightmarishly misconceived narrative and libretto—three twentysomethings sing an utterly gorgeous hymn to American opportunity and ambition.

“Feel the flow, hear what’s happening, we’re what’s happening,” they chorus. “We’re the movers and we’re the shapers, we’re the names in tomorrow’s papers, up to us now to show ’em. It’s our time, breathe it in. Worlds to change and worlds to win. Our turn coming through, me and you, man, me and you.”

The song is called “Our Time,” and as in so much of Sondheim’s work, it has a savagely ironic side to it—because we already know that these three young optimists will end up losing everything of meaning to them. The show begins with them in middle age, disappointed, cynical, and utterly without hope, and travels back in time to the moment of their surpassing optimism.

And yet there’s no irony to the song itself; its beauty only serves to highlight the surging optimism of “our time” as compared with the false and stale future the trio marches foolishly toward. And it’s meaningful that “Our Time” was written in 1981 rather than in 1957, because the passage of time seems to have afforded Sondheim the rueful knowledge of just what kind of a bounty he and his peers had received as young and ambitious Americans who had come into their adulthoods in the 1950s.

It had been their time because it had been America’s time. Give us room, they sing, and start the clock.

America gave Sondheim room, and he took it. And his death on November 28 at the age of 91 stopped the clock. His passing very nearly brings down the final curtain on the era of the self-confident, energetic, overpoweringly American 1950s.¹ He embodied that era, too, in a way, even though his greatest work would be produced decades after—and even though the highbrows of the day (like Irving Howe) certainly did not view his chosen form as any kind of cultural pinnacle.

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Sondheim entered Broadway as a preternatural force, with three classic shows—Gypsy and A Funny Thing Happened on the Way to the Forum would follow West Side Story over the next five years—under his belt by his 32nd birthday. But that astounding level of achievement did not give him the cultural standing afforded the painters and novelists of his day. The commercial theater was thought, by those who dominated the pages of this magazine and other critical apexes of American culture, to be the province of mostly intolerable middlebrows. Sure, a good show could be entertaining, but any good show was pretty much only that—a work of mere entertainment, not a meaningful exploration of the enduring themes of genuine high art. Sondheim’s medium was deemed essentially banal and of little enduring worth.

Sondheim’s West Side Story collaborator Leonard Bernstein (who composed the score) may have made his fortune and his name writing Broadway hit shows, but he was considered a lion of culture only because he also stood before the New York Philharmonic with a baton in his hand “interpreting” Mahler whilst tossing his hair like a model in a shampoo ad. And Jerome Robbins, who directed and choreographed West Side Story, was deemed an artist of true importance only because he “made” ballets—ballet being thought, for reasons that elude me, to be high art rather than the ludicrous kitsch some of us believe the form to be.

Sondheim was no Bernstein or Robbins. But he had been a pupil in his early twenties of the ferociously avant-garde composer Milton Babbitt. Later in his life, he explained that he had done so “to study composition, theory, and harmony without the attendant musicology that comes in graduate school.” What he learned from Babbitt, he said, “was basic grammar—sophisticated grammar, but grammar.” Babbitt told Sondheim’s biographer Meryle Secrest that his student hadn’t been “interested in becoming what one would call a serious composer, but he wanted to know a great deal more about serious music because he thought it would be suggestive and useful.”

The teenage Sondheim had had the inestimable good luck of knowing Oscar Hammerstein, the most commercially successful Broadway lyricist and veteran librettist. Hammerstein went line by line through the 15-year-old Sondheim’s first juvenile attempt to write a show. It is hard to think of two more divergent men of the theater. Hammerstein’s key quality was an earnest and deep-hearted plainness, while Sondheim combined an astounding wit with an allergy to the honest expression of simple emotion.

But Sondheim recognized that Hammerstein was a genius of a kind—a master not only of the form of popular songwriting but also of theatrical structure. Sondheim described his mentor as “a highly professional, highly rule-conscious man. He didn’t say obey the rules, he just pointed them out. He said, ‘Writing does not consist of saying, “Oh, I like that word.” Writing consists of choosing.’” What Sondheim understood was how extraordinarily sophisticated Hammerstein was in his simplicity, just as he understood that the fiercely difficult Babbitt was excessively dogmatic in his complexity.

The conflict between Babbitt and Hammerstein in the soul of Stephen Sondheim is the key to understanding the astonishing and enduring power of his work. The composer, Babbitt, was a postulant at the altar of deliberately obscurantist modernism. The lyricist, Hammerstein, believed and profited from his painstaking efforts to speak meaningfully (and profitably) to the greatest number of people in words and phrases they could understand.

Bernstein implicitly noted the influence of Babbitt on Sondheim when he observed that the score to A Funny Thing Happened on the Way to the Forum was filled with “wrong notes.” What he meant by this was that Sondheim almost perversely refused to resolve musical phrases in a conventional manner most pleasing to the ear. That is true even though Forum is easily the silliest show Sondheim ever worked on, an out-and-out farce without a serious moment in it (and by far the most commercially successful of the 13 shows for which he wrote both the music and lyrics).

What is most immediately captivating about Sondheim is the cleverness; he was likely the cleverest songwriter who has ever lived. His wordsmithery—triple rhymes, rhymes within rhymes—had an almost supernatural quality to it, especially because it seemed to spring from his head like Athena and not from a lifetime of literary aspiration. Indeed, he always flatly said that he was uninterested in such things. “I’m not a reader,” he said after producing two collections of his lyrics featuring insightful commentary about songwriting in general. “Prose is not a natural language for me.” He all but bragged about using a thesaurus to help him with his lyrics. (Someone raise Irving Howe from the dead and then quickly give him some smelling salts.)

But Sondheim’s wit wasn’t just revealed by his word choices. It sprang from his extraordinarily perceptive analysis of human behavior. One of his specialties was angry songs for angry characters whose bitterness makes them brilliant. A self-loathing middle-aged New Yorker sings of herself and her friends as “the ladies who lunch,” who are “off to the gym, then to a fitting, claiming they’re fat—and looking grim ’cause they’ve been sitting, choosing a hat. Does anyone…still wear…a hat?” Another woman in the same vein threatens her husband with divorce: “Could I leave you, and your shelves of the World’s Best Books, and the evenings of martyred looks, cryptic sighs, sullen glares from those injured eyes?”

Strikingly, his wit was just as evident in his music. He wrote pastiche songs as memorable as the ones he was parodying, as when he invoked Gilbert and Sullivan (“Please Hello”) to describe the Western encroachment on Japan in the mid 19th century in Pacific Overtures, or when he mimicked the Andrews Sisters as three young women lamenting a common boyfriend’s inconstancy in Company’s “You Could Drive a Person Crazy.”

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But as deeply as Sondheim represented the pinnacle of American cleverness, his work is actually about his mistrust of it—about people like him (one can assume) who are either unwilling or unable to embrace simple and basic truths. The title song of his 1964 flop, Anyone Can Whistle, is the perfect example. “What’s hard is simple,” sings the show’s female lead. “What’s natural comes hard. Maybe you could show me how to let go, lower my guard, learn to be free.”

His breakthrough show, 1970’s Company, is about a 35-year-old man who spends his life as the third wheel to a series of couples, “these good and crazy people, my married friends.” Unable to commit to any woman, he finally makes a tortured birthday wish—a wish that someone would come along to “crowd me with love,” he sings. “Somebody force me to care. Somebody let come through—I’ll always be there, as frightened as you, to help us survive being alive.”

This ambivalence was, perhaps, the greatest subject for ambitious American artists of Sondheim’s time. Indeed, they lived that ambivalence every day. They wanted to have it all (to use a phrase that was not yet in existence) in exactly the manner that made Howe cluck his tongue so disapprovingly. They wanted to be artists, to be academics, to be intellectuals, the very sort of people with the standing to rise above the manners and morals of the petit-bourgeois country they lived in, as such elitists always have. But they also wanted to talk to that country, to guide it, and to enjoy its bounties. They wanted to write important books—but they wanted those books to sell. They wanted to paint according to profoundly abstract theory—but they also wanted to sell those paintings to rich people and to hang in the Met.

The novels of Saul Bellow are shot through with the same sort of ambivalence. Seize the Day, published in 1956, concludes with its hangdog protagonist Tommy Wilhelm weeping at the funeral of someone he doesn’t know because he longs for exactly the same human connection as the protagonist of Company. Moses Herzog, the compulsive letter-writer at the center of Herzog, uses his formidable intellectual gifts to keep himself at a soul-threatening remove from ordinary life. One could say the same of Philip Roth’s profane Portnoy, whose complaint Roth defines at book’s end as “a disorder in which strongly felt ethical and altruistic impulses are perpetually warring with extreme sexual longings.”

These odd thematic similarities to the work of Bellow and Roth raises the question: What role, if any, did Sondheim’s Jewishness play in his work? He was raised by a first-generation Lithuanian Jewish mother who had herself been raised in a traditional household but later preposterously claimed to have been educated at a convent. Janet Sondheim (known as Foxy) designed dresses her husband manufactured—which meant that they were basically in the shmatta business. They divorced when Herbert Sondheim fell in love with a Catholic—and after marrying his second wife, Herbert never told his two subsequent sons he was a Jew. Sondheim’s biographer Meryle Secrest reports Stephen did not have a bar mitzvah and first entered a synagogue at age 19.

And yet, and yet. From an early age, Sondheim was hungry for entry not in a world of Gentile gentility, but one entirely dominated by Jewish men. And he would spend half a century almost entirely in Jewish company. His collaborators on West Side Story were Bernstein, Robbins, the librettist Arthur Laurents, and the producer Harold
Prince. He teamed on Gypsy with Robbins, Laurents,  and the composer Jule Styne. Forum’s book was written by Burt Shevelove and Larry Gelbart; the books for Pacific Overtures and Assassins were by John Weidman. Company began his seven-show run with Prince as a director. Later, he would create three shows with James Lapine. All in all, in a career spanning 51 years and 19 shows, Sondheim worked with two Gentile librettists² and one Gentile director³—and that was it.

But to judge by the subject matter he chose, Judaism and the Jewish experience were of limited interest to him. This was a man who wrote shows about a psychopathic Victorian barber, turn-of-the-century Swedes, Japan’s confrontation with the West, the painter Georges Seurat, the discontents of fairy tales, the assassins of American presidents—and never engaged with anything remotely close to a Jewish theme. The same cannot be said of his most distinguished collaborators. Robbins’s greatest triumph came with Fiddler on the Roof, which was produced by Harold Prince. Arthur Laurents’s first Broadway success was a play about anti-Semitism in the military called Home of the Brave. Bernstein was obsessed with Jewish subject matter; among other works, he wrote a symphony inspired by the Kaddish, the most important prayer in the liturgy, and set three Psalms to music in Hebrew.

And yet, like Sondheim, they were mostly deracinated. The problem for them was that true deracination was not yet really possible. Until the 1950s, socially ambitious American Jews were denied places in country clubs, white-shoe law firms, upper corporate management, and were subject to strict academic quotas. America was the most welcoming place Jews had ever lived, but Jews were still a people apart even if they never set foot inside a shul or they pretended to have gone to Catholic school. Jews like Hammerstein, whose father was a theater and opera impresario in the late 19th century, actually found a home in show business as they did in no other field in part because show business was an entirely new field of endeavor and therefore had no established barriers to entry.

That strange combination of being entirely and essentially American, and yet being apart even when you might not have wanted to be apart, helped provide Sondheim with the critical distance from convention that all great satirists and social critics possess. It has been said of Henry James that his ability to see so deeply into the nature of romantic and sexual conflict was due to some degree to his homosexuality. That Sondheim, who shared James’s often implacable eye, was himself gay also played a role in his apartness.

Though he was not happy with his homosexuality until relatively late in life, Sondheim knew himself too well to enter a marriage with a woman, as many similar men of his time did. He had many opportunities to do so—the actress Lee Remick wanted him even knowing his leanings, and so did Mary Rodgers (Richard’s daughter), among others. But he was a ruthlessly honest person and would not live falsely in that way. His soaring romantic songs are, as befits his chronic ambivalence, often savage commentaries on the very idea of love as a means of personal salvation. In Assassins, two young people duet on the prettiest tune he ever wrote. It’s called “I Am Unworthy of Your Love.” The two are would-have-been Reagan assassin John Hinckley, who is singing it to Jodie Foster, and would-have-been Gerald Ford assassin Squeaky Fromme, who is singing it to Charles Manson.

Assassins, which was first produced in 1991, is a full-frontal assault on the United States, as was Pacific Overtures 20 years earlier—both of which he wrote with librettist John Weidman. The former is about the supposed American love of violence, the latter about the evils of American imperialism. There’s no getting around this. His pitiless eye saw this country at its worst and then wrongly accepted the noxious idea that its worst was its nature.

There is something oddly Oedipal about it as well. Sondheim had a monstrous mother of a kind that even Philip Roth could hardly have imagined; he said she tried repeatedly to seduce him after his father’s abandonment, and in the early 1970s, just before she was to have open-heart surgery, she wrote him a letter that said, “The only regret I have in life is giving you birth.” It may be hard to experience the love of country when you were raised by a mother who, on occasion, openly wished you dead.

That same pitiless eye helps explain why most of the shows for which he wrote both music and lyrics are fundamentally unsatisfying. He could not bring himself to provide musical-theater audiences with emotionally revivifying conclusions because he did not believe in them. Only two of them rise above this critical flaw. The first is A Funny Thing Happened on the Way to the Forum, because it’s just a delight from beginning to end and wants nothing more than to amuse. The second is his darkest, Sweeney Todd, the Demon Barber of Fleet Street, which I believe to be the single greatest work of the American theater.

This sung-through semi-opera has no ambivalence in it whatsoever. It is a wild and incarnadine melodrama set in Victorian London about a homicidal maniac driven to psychosis who ends up murdering the very wife for whose honor he is seeking revenge. But in the course of its three hours, Sweeney Todd pays tribute to every emotion known to man in the most beautiful and vivid score he or any man of the theater has ever written. Sondheim, so clearly uncomfortable with the boundaries of ordinary life, was liberated by writing a show set in a world in which there is no ordinary life and there are no boundaries.

“Life was fun, but oh, so intense,” sing four middle-aged people as they look back starry-eyed on their youth in his 1971 show Follies. “Everything was possible and nothing made sense.” Indeed, the life story of Stephen Sondheim is a testament to how everything was and is possible in America. That was true in the 1950s, even if—or maybe because—you were uncomfortably Jewish and uneasily gay. And it remains true today, even if—or maybe because—we can’t see it through the present-day haze.

Everything is possible. It’s not inevitable. It’s not your due. It’s just the chance America gives you.

^{1 Only two other famous talents from that era, Woody Allen and Mel Brooks, survive; Brooks has just published a memoir called All About Me at the age of 95. Allen’s own memoir, Apropos of Nothing, came out last year, and its opening chapters about the sociopathic father in whose sociopathic footsteps he would later unconsciously walk are astonishing.
2 George Furth wrote the books for Company and Merrily We Roll Along. Hugh Wheeler wrote the books for A Little Night Music and Sweeney Todd—if Sweeney Todd, which is an almost entirely sung-through opera, can even be said to have a book, and indeed, Sondheim discarded much of the work Wheeler actually did.
3 The director was John Doyle, and the show was Bounce, his last to be produced, in 2008; interestingly enough, Sondheim had been gestating a version of the show, about the Florida land rush, since the early 1950s, and after three stagings under different titles from 1999 until 2008, never cracked it. What’s more, the director of the 1999 version, under the name Wise Guys, was the Briton Sam Mendes, another Jew.}

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