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When Stephen Sondheim died in late November at ninety-one, the eulogies, tributes, and bouquets from critics and ­tastemakers were entirely expected. The Broadway composer and lyricist left the Earth having earned multiple Tonys and Grammys, a Pulitzer Prize, an Oscar, a Kennedy Center Honor, and a Presidential Medal of Freedom. Though he soldiered through some flops, his mature musicals were the rare works that never required critical resuscitation: They were acclaimed the day they premiered and adored the day he died.

Cornel West has namechecked Sondheim’s shows for years; ­Stephen Colbert treated Sondheim as a guru when, this past fall, he logged an appearance on Colbert’s late-night show. Critical huzzahs greeted Steven Spielberg’s remake of West Side Story, for which ­Sondheim wrote the lyrics and which was released weeks after his death. ­Sondheim’s colossal stature endured in 2021 despite the fact that he had produced no new work since the late 1990s.

As a young man, Sondheim had fallen under the tutelage of Oscar Hammerstein II, lyricist and book-writer for such seminal Broadway shows as Oklahoma!, The King and I, and The Sound of Music. Though Sondheim played up his eagerness to follow in Hammerstein’s footsteps—“If Oscar had been a geologist, I would have become a geologist”—his most famous shows strayed far from the box socials and state fairs conjured by his mentor. Sondheim was often drawn to subversion and experimentation, favoring subjects that were either perverse (the exploits of a murder-­mad barber and his cannibalistic partner in crime in Sweeney Todd) or esoteric (the life and times of French pointillist painter ­Georges Seurat in Sunday in the Park with George). And he felt no need to emulate ­Hammerstein’s partnership with composers Jerome Kern or Richard Rodgers, more often than not composing music proud in its unhummability.

For all these reasons, Sondheim represents a turn in American musical theater toward subverting the themes and styles that had characterized the form when it was dominated by the men from whom he learned his trade: affirmations of the important things in life, such as family and romantic love, expressed through melodic, lilting music. Sondheim’s supremacy in musical theater owes much to his cynicism about men and women, disenchantment with the American ideal, and enchantment with what is ­­marginal—­attitudes that mirror those of our cultural elites. ­Whereas the Rodgers and Hammerstein songbook appealed to both the elite and the ordinary, to coastal as well as Middle America, Sondheim never attempted to get Americans singing the same tune. In Sondheim’s shows, the elite ­serenades itself.

Sondheim was born in 1930, the only child of Jewish parents in New York. They divorced when he was ten, an unfortunate twist of fate—­Sondheim claimed his mother expressed regret at having given birth to him—that turned out to have a major advantage: ­Residing with his mother in Bucks County, Pennsylvania, brought him into the orbit of the Hammersteins. ­Sondheim became a kind of auxiliary son to ­Oscar. He later told the ­Paris Review that when he presented ­Hammerstein with a juvenile attempt at a musical, the Broadway legend asked whether he wanted a fair evaluation. “‘Oh yes,’ I said, to which he replied, ‘In that case, it’s the worst thing I’ve ever read.’” But ­Hammerstein’s ­dissection of the musical’s defects was all the education Sondheim needed. “In that afternoon I learned more about songwriting and the musical ­theater than most people learn in a ­lifetime.”

Hammerstein’s mentorship, which continued until his death in 1960, was evident in Sondheim’s earliest Broadway work. These shows, solidly within existing traditions of musical theater, bore the fingerprints of others: West Side ­Story (1957), with music by ­Leonard ­Bernstein, seemed to build on ­Rodgers and Hammerstein’s South Pacific in concerning itself with timely social issues. Gypsy (1959), with music by Jule Styne, was in the genre of “backstage musicals.” A Funny Thing Happened on the Way to the Forum (1962), an adaptation of Plautus for which Sondheim provided lyrics and music, was tuneful in a way his future work rarely sought to be.

As Sondheim’s reputation grew, and he gained the ability to develop his own projects and ­consistently write both lyrics and music, he ­began to shed the influences of his forebears. The convoluted rhythms, complex polyphony, and at times atonal quality of his music often resist easy listening. Like Seurat in Sunday in the Park with George—­depicted in the song “Finishing the Hat” as toiling on works of great but arcane significance while ­lesser beings go obli­viously about their lives—­Sondheim seemed to prize that which challenges or provokes rather than that which pleases or nourishes.

Few could deny Sondheim’s gift for arranging words in ways that tickled the mind—think of the cornucopia of verbiage in “Getting Married Today” from Company (1970). Nor could they deny his formidable intelligence, on display in a range of intriguing side projects, including cryptic crosswords for New York magazine (1968–69) and the screenplay for The Last of Sheila (1973), an ingenious murder mystery co-written with Anthony Perkins. But to what end? Sondheim dissented openly from the sensibility of Hammerstein, a proud left-­liberal who nevertheless retained a faith in the eternal verities: God, family, country, and all that.

In two collaborations with book-writer John ­Weidman, Sondheim set himself the task of contesting our country’s story of itself. Set in nineteenth-­century ­Japan, Pacific Overtures (1976) presents the West’s influence on the East as the stuff of catastrophe, or farce. In the almost cartoonishly dumb song “Please Hello,” an American admiral barrages his Japanese host with lines such as: “Last time we come, come with warships, / Now with more ships— / Say ­hello! / This time request use of port, / Port for commercial intention, / Harbor with ample dimension.” Meanwhile, the Dutch admiral promises chocolate; the Russian admiral seeks to protect his precious coat. So much for Rodgers and ­Hammerstein’s vision, in ­Oklahoma!, of a nation expanding confidently and honorably or, in The King and I, of healthy cultural exchange between ­civilizations.

More provocative still was ­Assassins (1990), in which the stage is turned over to fictionalized versions of a most sorry lot: those who either took the life of a U.S. president or attempted to, including John Wilkes Booth, Lee ­Harvey Oswald, and John Hinckley Jr. Here we have not merely ill-­advised ­humor—as in “Unworthy of Your Love,” in which Hinckley and Squeaky Fromme goofily express their devotion to Jodie Foster and Charles ­Manson—but also something more pernicious: an attempt to render the assassins’ motives comprehensible, the workings of their minds intelligible. “They were entirely different people, but they were motivated by a similar kind of passion,” Sondheim said in the New York Times. “Some were less than crazy, and some were more than crazy.” Imagine the outrage if someone on Broadway put on an all-singing, all-dancing show about the January 6 rioters.

Even Sondheim’s less overtly political shows offer an agenda fundamentally at odds with the vision of America as a fair land that welcomes all and whose influence is, in turn, welcomed around the world. In West Side Story, the song “­America” anticipates current far-left politics in insisting on the impossibility of the ideal of assimilation—“Life is all right in America / If you’re all-white in America”—and the un­reality of the American Dream: “Free to be anything you choose, / Free to wait tables and shine shoes.”

Sondheim came of age before the counterculture, let alone the era of wokeness, and when he spoke about theater, his attitudes could, at times, be refreshingly traditional. He was gay but did not come out until his early forties, and he pushed back against the cult status of West Side Story’s “Somewhere” (“If you think that’s a gay song, then all songs about getting away from the realities of life are gay songs”). More recently, he was a lone voice protesting the cognitive dissonance of Lady Gaga’s performing from the Sound of Music songbook at the Oscars: “It was ridiculous. . . . She had no relationship to what she was singing.”

But his work more often reflected countercultural attitudes. He insisted that Company—about a swinging young man’s aversion to marriage—was not “anti-­marriage,” yet the show certainly expresses skepticism of matrimony in such songs as “The Little Things You Do Together,” a litany that includes “neighbors you annoy together” and “children you destroy ­together.” This skepticism is not entirely expelled in “Being Alive,” a finale that notably celebrates not marriage but constancy. Its bland, vague endorsement of monogamous companionship could comport with any number of relationships that fall outside the holy estate as ­traditionally defined.

Sweeney Todd: The Demon Barber of Fleet Street (1979) is arguably Sondheim’s most lasting work. Its pitch-black, penny-­dreadful-based plot—about Victorian barber ­Sweeney Todd, who offers up his customers as fillings for his friend Mrs. Lovett’s pies—must be understood as part of a long and honorable tradition of satire, black comedy, and other mischief in the literature of the West. But it is downright ­incongruous as fodder for musical theater. Available on the internet is footage of Sondheim coaching a performance of “My Friends,” in which Todd addresses a straight-edged razor as though it were a lover. Sondheim tells the actor, with a bit too much relish: “If you were singing a love song to a girl, you wouldn’t look that way. You’d look to her. So look at the razor, speak to the razor, make love to the razor.”

Todd commences his killing spree in order to exact retribution for the fate his wife and child befell at the hands of a lecherous judge. But Sondheim foregrounds Todd’s revenge, not his anguish: Remember, “make love to the razor” (and not to a girl). Sweeney Todd is a clever farce and a Grand Guignol romp; it’s also a stark departure from the sort of material that had made American musical theater great. In one generation, the form went from Hammerstein’s hymn to indomitability, “Climb Ev’ry Mountain,” to Sondheim’s gag about cannibalism, “God, That’s Good!”—thanks in part, ironically, to the helping hand the older man extended to the younger.

But is it so subversive that it restricts its own influence? Sweeney Todd doesn’t seem likely to become as ubiquitous as The Sound of Music; with its forbidding style and repulsive action, it plainly isn’t trying to. Even the remake of West Side Story, Sondheim’s traditional early-career work and his biggest crowd-pleaser, has failed to ignite at the box office, suggesting the limits of his popularity outside of urban elite culture. After a long period of divisiveness, perhaps a musical about cultural incompatibility, and the supposed inhospitality of America to new arrivals, isn’t what the country is hungering for, not even when the music is by ­Leonard Bernstein.

Sondheim’s rise reflected a ­broader estrangement of the masses from the tastes and attitudes of the cultural vanguard. In 1959—when the New York Times best-seller list was topped for much of the year by ­Doctor ­Zhivago, and the top-grossing film was Ben-Hur—Truman Capote could say of the free-form style of the Beat writers, “That isn’t writing at all, it’s typing,” and expect that most of the public would agree. They probably still would, but the literary progeny of the Beats are no longer on the margins. They’re at the epicenter of the literary world, as Sondheim was of the theatrical world.

Of course, American musical ­theater is less central today than it was. If art forms that once were widely popular are increasingly aimed at the beau monde, the trend is exacerbated in live theater thanks to its geographic ties to large urban centers. Rodgers and Hammerstein felt compelled to address both town and country, and town and country returned the favor by making their shows iconic. Sondheim worked for, and reflected the prejudices of, a narrower audience. On December 8, all the marquees on Broadway went dark for one minute in remembrance of Sondheim, and though the tribute was well deserved, it was a testament to both his centrality to the few and his irrelevance to the many. After all, Broadway lights don’t reach as far as flyover country.

Peter Tonguette writes from Columbus, Ohio.

Image by Portland Center Stage via Creative Commons. Image cropped.