Updated at 11:10 a.m. ET on December 3, 2021
It was Madonna who first introduced me to Stephen Sondheim, which sounds infinitely more chic than what happened in reality: Someone gave a 7-year-old girl a cassette of I’m Breathless, the 1990 album Madonna recorded during her gauzy showgirl period, pegged to her role as Breathless Mahoney in the movie adaptation of Dick Tracy. At the time, Cats had been running on Broadway for eight years. I had recently furthered my own artistic evolution by playing the title role in our class production of Joseph and the Amazing Technicolor Dreamcoat. Musical theater in London was largely defined by plasticized melodies, Schönberg and Boublil, and soap-opera stars grinning out from West End billboards.
But lurking within I’m Breathless—among dubious Carmen Miranda impersonations (“I’m Going Bananas”) and odes to light S&M (“Hanky Panky”)—were three works written by Sondheim. The film’s director and star, Warren Beatty, had asked the composer and lyricist to contribute five original songs, three of which made it onto the album. They vary drastically in style. “More” is a jaunty anthem to avarice that’s also a tricky retooling of lyrics cribbed from the Great American Songbook. “Sooner or Later” is a smoky ballad that expresses both Breathless’s sexual fixation on Dick Tracy and Tracy’s charged compulsion to lock up his criminal nemesis. “What Can You Lose?,” a duet between Madonna and the frequent Sondheim collaborator Mandy Patinkin, is a torch song about bottling up unrequited love. All three works are, in their way, expressions of yearning, the profound emotional core of Sondheim’s work. Given a relatively simple assignment—write some songs for a comic-book movie!—Sondheim delivered a puzzle disguised as pastiche, an Oscar-winning theme song that complicates the rigid masculinity of an American icon, and a heartbreakingly circular expedition through romantic hope, doubt, and repression that occupies a mere two minutes.
With his songs for Dick Tracy, Sondheim, who died on Friday, did what he did throughout his career: engaged with a traditional discipline while simultaneously cracking it open from within. He was the modernist of musical theater, turning a comfortably staid genre into a knotty, disaffected, aching form of experimentation. He made the musical new. He brought a mathematician’s mind to the business of lyricism, confronting each song as a conundrum of marrying emotional clarity with melodic emphasis and the structural limitations of rhyme. But, crucially, he also made art for outsiders, which is why his most devoted fans tend to be artists. Sondheim’s work takes the typically unseen—aging women, married couples, bystanders—and forces them into the spotlight.
Once you connect with Sondheim, you’re his forever. No one else captured love as he did—not as a prize, or as an ending, but as something fleeting, hungered for, impenetrable, or even toxic. (One of my favorite songs of his is “Unworthy of Your Love,” from Assassins, in which John Hinckley Jr. and Lynette “Squeaky” Fromme sing poignantly about their ardor for Jodie Foster and Charles Manson.) Starting with Saturday Night, his first professional musical, which he finished writing in 1954, Sondheim’s characters were people on the margins with a fierce longing to be center stage. Their desires are profound, if not always straightforward. Before Sondheim, musical theater was largely defined by characters whose hearts were squarely and earnestly pinned on their sleeve: “Singin’ in the Rain,” “I’m in Love With a Wonderful Guy,” “I Hate Men.” What he introduced to the genre was simple but revolutionary: subtext. His peers weren’t Lerner and Loewe so much as Pinter and Albee, iconoclasts intent on a more charged engagement with the modern condition.
But musical theater, midway through the 20th century, wasn’t a form characterized by innovation. Sondheim’s work often perplexed and even irritated audiences, not to mention critics, who maligned his lack of “hummable” songs and—in the case of John Lahr—accused him of killing the exuberant, old-fashioned musical. It’s not that Sondheim doesn’t offer, in moments, pure musical catharsis—the soaring, emphatic crescendo of “Aren’t they a gem?” or “the grass or the stick or the dog or the light.” It’s that, as Stephen Schiff wrote in a shrewd 1993 New Yorker profile, “Sondheim’s accompaniments are sumptuous, but they don’t allow a melody to plunk neatly into place; they don’t allow it to resolve; they don’t give it a home.” His composed works are reticent: They tantalize but hold back total gratification.
Sondheim long resisted the idea that any of his work offered a read into his own psyche, and elements of his own identity—his sexuality, his Jewishness—are defiantly absent from his art. His songs, he insisted to the writer and his longtime friend Frank Rich, have “nothing to do” with him and are rather fully realized outpourings of fictional characters. At the individual level, I’d say this is true (although Company’s confirmed bachelor, Bobby, seems to have distinct shades of a man who didn’t enter a meaningful romantic relationship until his 60s). But as a whole, his work is shot through with a kind of detached but intense longing, the loneliness of one who knows love can’t be trusted. This duality is hard not to tie to Sondheim’s mother, an emotionally abusive woman who, he wrote, interspersed verbal beration of her son with inappropriately sexualized ploys to get his attention. Later in life, she wrote him a letter saying that giving birth to him was her life’s one regret. When she died in 1992, Sondheim didn’t go to her funeral.
Sondheim’s strikingly bitter childhood was sweetened by circumstance: His mother was friends with the wife of Oscar Hammerstein II, and the lyricist became his champion and mentor. Without Hammerstein, Sondheim writes in Finishing the Hat, he might never have become a songwriter. And yet, with a kind of Oedipal glee, he also uses the book to distance his work from that of a man who, he proclaims, “is not my idol.” The truth, he writes, “is that in Hammerstein’s shows, for all their revolutionary impact, the characters are not much more than collections of characteristics—verbal tics and quirks … Refining his innovations was left to my generation.” Nevertheless, Hammerstein gave Sondheim a master class in both craft and work. Writing, Sondheim came to understand, wasn’t about thunderbolts of inspiration but the careful honing of techniques in service of experimentation. Though he claimed that he never cooked, he read cookery columns with fanatical devotion, comparing the technical details of “timing, balance, form, surface versus substance” to the alchemy of songwriting.
It was on Hammerstein’s advice that Sondheim accepted his first major jobs as a precocious lyricist: 1957’s West Side Story, with Leonard Bernstein and Arthur Laurents, and 1959’s Gypsy, with Laurents and Jule Styne. With the former, Sondheim largely felt pigeonholed into Bernstein’s lush, romantic vision for the show, but with Gypsy, he writes in Finishing the Hat, “I came of age—lyrically, at any rate.” The characters (not least, one imagines, the monstrously narcissistic and self-deluded stage mother Rose) “were types familiar to me.” And the narrative, he felt, had more dramatic weight and complexity than the products of Broadway’s earlier eras. Yet Gypsy, for all its vibrant theatricality and old-fashioned grandeur, also has a decided sourness to it. That’s not a critique—more an assessment of how the show acknowledges the hustle at the heart of the American dream, the innate ugliness of striving and manifesting a vision.
A Funny Thing Happened on the Way to the Forum, the first show to feature both music and lyrics by Sondheim, was a hit in 1962 and scored six Tony Awards, including Best Musical. But it was 1970’s Company that really outlined Sondheim’s virtuosity and variation. Devised initially with the playwright George Furth as a series of loose vignettes on the subject of romantic relationships, Company was formed into a show by the addition of Bobby, a single man staring down 35 while his various “good and crazy” married friends urge him to settle down despite their own states of unhappiness. Sondheim initially had no sense that the show would seem so unsettling to audiences. The primary elements of musical theater—humor, cheerful melodies, “I Want” anthems—are all present. But coming after the ’60s, at the tail end of the Summer of Love, Company’s defining quality, its skepticism and ambivalence toward partnership, felt too cataclysmic for some. Musicals were supposed to ratify love as a guiding ideal, not disrupt it altogether. Lurking beneath the surface of Company is an idea that Bobby’s ambivalence isn’t his own—that the structures holding social and romantic relationships together are destabilizing in front of the audience’s very eyes.
“‘Cold,’” Sondheim writes, “is an adjective that frequently crops up in complaint about the songs I’ve written, both individually and in bulk, and it all began with Company.” The show, like most exceptional works of postmodernism, is suffused with irony and disenchantment with the tentpole narratives of Western culture. Broadway-goers more accustomed to romanticized stories of self-actualization may have balked, but the musical, as Schiff wrote, “felt grown-up,” perhaps for the first time. It suggested a new model for what the form could do and be. Follies, a devoted eulogy for the bygone days of musical theater that confronts the absurdity of its characters’ dreams in show business, was even darker and more neurotic. With every show that followed (a musical about the Westernization of Japan, a musical about cannibalism, a musical about sacrificing your artistic integrity, which goes backward in time), Sondheim seemed to be testing every limit he could throw himself against.
Not every show was a success—the majority weren’t initially, although they came to be appreciated later—but each has its defenders and detractors. Sunday in the Park With George, a 1984 show about the painter Georges Seurat that processed some of his feelings of failure regarding 1981’s Merrily We Roll Along, is one of my favorites for the sweep of its ambition and the sharpness of its yearning amid an acknowledgment that making art is inherently isolating. But Into the Woods, a 1986 pastiche of the fairy-tale musical, seems, to me, the capstone of Sondheim’s career. It’s not the greatest of his works, or the most blazingly innovative, or even the most fun. Rather, it feels like the culmination of so many things that defined his craft: the challenging of archaic story forms, the acknowledgment of life’s arbitrary cruelties, the pairing of dissonant melodies with moments of striking musical purity.
“Sometimes people leave you / Halfway through the wood,” the Baker’s Wife sings in the finale of Into the Woods. “Do not let it grieve you / No one leaves for good.” If the moment feels oddly sentimental for a writer who’s such a cockeyed realist, it’s countered by Cinderella’s version of the line in an earlier song: “Others may deceive you / You decide what’s good.” This essence of choice and ambiguity and convolution is what Sondheim gave to theater—the idea that there’s infinitely more contained within the tragicomedy of human experience than can ever be set to music and sung on a stage.
A photo caption in this article previously misidentified the actor Ben Lewis.