Stephen Sondheim: An Unlikely Songwriter for Our Times

“Stephen Sondheim is possibly the best lyric writer this country has ever produced,” Randy Newman told me in 1996. “Dylan at his best may be better, but Sondheim is at his best more often. Sondheim has always written for adults. He’s a great lyricist, technically brilliant, who never condescends to his audience. A play like Passion, which I saw, is an integrated work, like a sonata form, like a movement in a symphony. Things recur. It’s like bumping into someone who has a great mind, but he can also do West Side Story.”

Sondheim, who died Friday at the age of 91, was an anomaly: a giant of the musical theater in an era when the center of gravity in American music had shifted from the stage to the pop recording studio. But such was the scale of his achievement that he couldn’t be ignored—neither inside, nor outside the insular world of Broadway. During a period when the biggest hits in musical theater came from bombastic, middlebrow merchants such as Andrew Lloyd Webber and Alain Boublil, Sondheim proved that the genre was still capable of greatness, and served as a role model for younger writers such as Lin-Manuel Miranda, Adam Guettel and Jonathan Larson.

The delightful new Netflix movie, tick, tick … BOOM! captures this passing of the torch. The film is Miranda’s debut as a director, and it tells Larson’s story through a recreation of his one-person show of the same title. This focuses on the period long before Larson died on the eve of his triumphant show Rent, on the years when the songwriter was working in a diner, struggling to pay his bills and writing musicals that few people cared about.

One person who did care was Sondheim himself. In the new movie, the bearded, slouching mensch attends the workshop read-through of Larson’s stillborn show Superbia. As played by West Wing star Bradley Whitford, Sondheim tries to slip unobtrusively into the back row of seat, but such is his force field that everyone—including Larson, played by Andrew Garfield—falls silent in awe for a moment.

And later, after a string of bad news—the producers pass on his show; his girlfriend splits—the down-and-out songwriter hears a message of encouragement from Sondheim on his phone machine, and that’s enough to make Larson light up. Miranda brings a vibrancy to these scenes, because he, too, went through such a phase. But during those lean years before In the Heights and Hamilton, Miranda kept at it, thanks in part to similar encouragement and mentoring from Sondheim.

If you know anything about musical theater at all, you understand why so many were in awe of Sondheim. It wasn’t because he was a commercial behemoth. His shows did respectably enough that someone was always willing to mount the next one, but his shows seldom ran for more than a year. And yet they keep getting revived, long after the bigger hits have been forgotten, because they’re miracles of weaving music and lyrics into a story so naturally that the songs never seem an interruption, only a shift in gears.

Sondheim got a lucky break early on. When he was 10, he met his mother’s best friend and the friend’s husband, Oscar Hammerstein, the lyricist who collaborated with Richard Rodgers on shows such as South Pacific, Oklahoma, Carousel and The King and I. Hammerstein took the teenager under his wing and taught him, Sondheim later claimed, more about writing songs for the theater than most people learn in a lifetime.

It was out of gratitude for Hammerstein’s help that Sondheim reached out to younger songwriters like Miranda, Larson and Guettel. In fact, after seeing tick, tick … BOOM! the week of his death, Sondheim messaged Miranda to say, “Thanks for the nice boost to my spirits, Lin. It’s an aspect of my life that I’m proud of. I feel as if I’ve repaid (partially at least) what I owe Oscar.”

Sondheim got a further break when he was invited to write lyrics for a musical adaptation of Shakespeare’s Romeo and Juliet, with music by Leonard Bernstein and dialogue by Arthur Laurents. That show, 1957’s West Side Story, became a classic of American theater. Bernstein and Sondheim teamed up again on another triumph, 1959’s Gypsy. Less successful was 1965’s Do I Hear a Waltz?, Sondheim’s collaboration with an aging, alcoholic Rodgers. At that point, Sondheim resolved to work only on shows where he could write both the words and the music, as he had always wanted.

To make that happen, he hooked up with director Hal Prince. The partners created five shows (with three different book writers) that are still considered musical theater masterworks: Company (1970), Follies (1971), A Little Night Music (1973), Pacific Overtures (1976) and Sweeney Todd: The Demon Barber of Fleet Street (1979).

In contrast to his mentor Hammerstein, whose wholesome optimism was a trademark of those hit shows with Rodgers, Sondheim wrote lyrics with an undercurrent of bitter irony, more like Rodgers’ earlier lyricist, Lorenz Hart. Like his words, Sondheim’s music also hinted that life didn’t always reward good intentions and fair play; the dark harmonies and twisting melodies reinforced the verbal hints that hopes are as likely to be frustrated as not. This was a very different approach to musical theater than the standard operating procedure, and made him both a heroic iconoclast and commercial risk on Broadway.

No show made these tendencies more explicit than Sweeney Todd. The story is based on the 19th-century legend about Todd, a London barber who pulls his razor too deeply across his customers’ throats and who then donates their remains to Mrs. Lovett, who owns the downstairs meat-pie shop. Her strangely delicious pies are suddenly selling as fast as she can bake them. In this era, at the infancy of capitalism, no one suspects these successful shop owners of anything nefarious.

In fact, the bubbly, cheerful Mrs. Lovett is willing to overlook any problems—dead people who should be alive and living people who should be dead—that might derail her booming business or her romantic designs on Todd. The barber’s tortured conscience, however, is outweighed only by his vengeful anger toward a society that sent him to prison and took away his wife. This contrast allows Sondheim to follow a brooding song like “Epiphany” with the black humor of a song like “A Little Priest,” which assesses the difference that a clergyman makes when added to the pie recipe. Every time the audience is on the verge of rebelling against the gruesome subject matter, Sondheim’s wit and seductive melodies pull us back in.

Wishing to push this approach even further, Sondheim teamed up with director/book writer James Lapine for a trilogy of shows that rank with Sweeney Todd as his best. Sunday in the Park with George was based not on a play or a novel, but on a painting: Georges Seurat’s 1886 pointillist masterpiece, “A Sunday Afternoon on the Island of La Grande Jatte.” This 1984 show invented a story for each person in the painting in a terrific first act and then tried to do the same for Seurat’s great-grandson in the 1980s art world in a less successful second act. Nonetheless, the musical play won Sondheim and Lapine the Pulitzer Prize for drama.

This method of mirroring and contrasting a show’s two acts was employed more successfully in 1987’s Into the Woods. Based on the Brothers Grimm’s fairy tales, the first act delivers those stories with all the wish-fulfillment happy endings that Broadway had reliably supplied to its audiences over the decades. In the second act, however, those same stories are allowed to unspool past the “happily ever after” punctuation into the misunderstandings, betrayals and losses of real life.

Thus the show critiques not only the fairy-tale fantasies that popular entertainment provides us, but also the delusions we cling to in our own lives. The show contains some of Sondheim’s best songs—especially “Giants in the Sky” and the much-covered “No One Is Alone”—and the 2014 movie version with Meryl Streep, James Corden and Emily Blunt is the best film version of a Sondheim show.

Closing out the Lapine trilogy was 1994’s Passion, which tells the story of Fosca, a sickly, unattractive woman who pursues Giorgio, a handsome, popular captain in the Italian army during the mid-19th century. Against all odds, he falls in love with Fosca and leaves Clara, his beautiful mistress, much to the bewilderment of his fellow soldiers. Thus the show raises the question we so often ask ourselves in real life: How did those two people ever get together? And it asks a question that we often ask in the theater: How have we been convinced that such an unlikely thing really happened?

We’re convinced by the patient, subtle, step-by-step changes in the music. As the show begins, Clara the mistress has the buoyant, major-key tunes, while Fosca has the brooding, minor-key numbers. But the latter songs are strangely seductive, and as Giorgio’s affection gradually shifts from one woman to the other, the music changes, as well. Fosca takes over the hopeful, bright passages, and Clara is left with the despairing, dark parts.

Sondheim finished three more shows after Passion: 1990’s Assassins, 1997’s Saturday Night and 2003’s Bounce. All of them had both sparkling moments and deep flaws. In an interview just before his death, Sondheim claimed to be working on another show based on Luis Bunuel’s films.

Unlike an earlier generation of Broadway songwriters such as Cole Porter, George Gershwin and Irving Berlin, Sondheim didn’t write songs that were frequently covered by jazz and pop singers. The most notable exception was “Send in the Clowns” from A Little Night Music, which boasted an undeniable chorus hook. Frank Sinatra recorded it in 1973 for his top-15 pop album, Ol’ Blue Eyes Is Back. Judy Collins released it as a single in 1975 and it eventually became a top-20 pop hit. Barbra Streisand released it as a single in 1986 and had a top-25 adult-contemporary hit.

Collins and Streisand regularly recorded Sondheim’s songs, but few other pop singers did. Madonna did invite Sondheim to write three songs for her 1990 album, I’m Breathless: Music from and Inspired by the Film Dick Tracy. They were good songs and she did a creditable job with them, but they were overshadowed by the album’s non-Sondheim hit single, “Vogue.”

And yet Sondheim had a telltale influence on a certain kind of modern songwriter, the piano-playing, storytelling singer/songwriter. Most notable of these was Newman, who has to be in the conversation about America’s greatest lyricists. He wrote the songs for three narrative projects: the pilot TV episode of Cop Rock in 1990; his own stage musical, Faust, in 1995; and the Disney animated musical The Princess and the Frog in 2009.

“I talked to Sondheim at a workshop for Faust,” Newman told me. “He scolded me for rhyming words like ‘girl’ and ‘world,’ or ‘band’ and ‘can.’ “That’s rock ’n’ roll writing,’ he said; ‘You don’t come from that tradition.’ But I do. I come from that tradition of Fats Domino rhyme schemes. Maybe ‘band’ and ‘can’ doesn’t work, but somehow it’s alright with me. I admire Sondheim, but I don’t come from the same tradition at all. Sondheim is the product of the pre-1954 pop song repertoire, along with Puccini. I am post-that.

“Paul Simon, Prince, Sting, The Beatles weren’t drawn to write for the theater; they were drawn to write for themselves. As a result, the best music for years hasn’t been written for the theater, it’s been written for pop music. There have only been a few exceptions, like Bernstein or Sondheim.”