Up Close and Very Personal With the Real Stephen Sondheim

In 2012, Stephen Sondheim, then 81, was still determinedly focused on working, creating—the process he famously called the hat.

In his New York City home, he told this reporter for a London Times profile, “I’m not a retiring type. I’m not a golf player. I can’t imagine sitting in front of the television. Painful as it is, writing is still fun and I don’t have anything else to do.”

“Obviously, I think about my mortality, particularly when your friends are dying—all my collaborators on West Side Story and Gypsy are dead. I’m the only one left,” Sondheim added, as he showed me his piano and orderly-cluttered work space in his Turtle Bay townhouse.

“I would love to live my life again knowing what I know now,” Sondheim told me. “I might enjoy things more fully, appreciating moments for what they were instead of taking them for granted.”

Now Sondheim has died at the age of 91, as first reported by The New York Times. The pre-eminent composer-lyricist and godfather of modern musical theater—responsible for such classics as West Side Story, Gypsy, and Into the Woods—passed early Friday after celebrating Thanksgiving with friends in Roxbury, Connecticut, where he lived, his lawyer told the newspaper. His death had been sudden, the lawyer added. He is survived by his husband Jeff Romley, whom he married in 2017.

Stephen Sondheim’s 90th Birthday Party Was the Best Broadway Fever Dream

With a career that spanned half a century, Sondheim had a slew of awards: nine Tonys, including a Tony for lifetime achievement, the Presidential Medal of Freedom, a Pulitzer Prize, and a Kennedy Center award for lifetime achievement. He even had a Broadway theater named after him.

Yet Sondheim was dismissive on the subject of his legacy, musing in my 2012 interview how “gratifying” it was to see revivals of his shows be mounted in New York and London. “It means the shows have lasting value. But posterity doesn’t interest me. I want to enjoy it while I’m here; I can’t after I’m dead. If I can’t see or hear an audience’s reaction, what’s the point? Maybe the minute I’m dead nobody will do any of my shows again, maybe they will do them every day of the year. It’s irrelevant to me.”

“Aging is no fun,” he told me in a later interview in 2015. “My memory isn’t sharp. All your energies diminish. You don’t want to make any more friends than you’ve made and they’re all dying anyway. You want to leave the house less. I don’t want to even leave the couch to go to the next room. I rode a bike to Broadway for 20 years. You get to know every pothole in New York. Watch me climb the stairs and you’ll know I’m an old man climbing the stairs. That also happens at the piano.”

He said he contemplated his mortality “all the time. You find yourself thinking more about death than about life. Work is the great revivifier.” As for the idea of retirement, Sondheim scoffed: “I don’t know what that means.”

Sondheim forcefully denounced modern Broadway. “Most interesting plays are done off-Broadway because there isn’t a public any more for plays, unless they feature a star, in which case they will go to see the star; it doesn’t matter what the play is,” he told me. “The same is true of musicals. There is an anodyne homogeneity that governs Broadway musicals, so I don’t see many. There’s nothing wrong with having a lot of commercial crap as long as you have something else. You want a supermarket. Unfortunately, nearly everything on Broadway is commercial crap. The same is true of the West End. When I scan what’s on, my heart sinks into my boots.”

Was the condition terminal, this reporter asked. “I think so. Commercial theatre will only get more narrow as time goes on. There are so many forms of entertainment, theatre is becoming more marginalized. It’s become ‘an event’: you see Wicked on your anniversary. I don’t think commercial theatre can fulfill a function as a constant feeding ground for emotions and thoughts.”

The challenge, Sondheim said, was to keep his work fresh. “It’s a very thin, maybe invisible, line between your style and cliché. If I play my favorite chord, am I repeating myself or is that who I am?”

On the occasion of Sondheim’s 90th birthday last year, a correspondingly impressive, star-studded online celebration was mounted in his honor. This reporter wrote, “Sondheim doesn’t just make us laugh and cry, he makes us think, examine, touch the open wound, and see the absurd, macabre, painful, delightful, and revelatory in our relationships with others and within ourselves.”

The phalanx of stars singing Sondheim songs included a bathrobe-clad, wine-glass wielding Meryl Streep, Audra McDonald, and Christine Baranski belting out “The Ladies Who Lunch” from the musical Company.

A revival of Company, starring Patti LuPone and Katrina Lenk, is playing on Broadway, while Assassins is at the classic Stage Company off-Broadway. Sondheim traveled to New York to see both shows this month, receiving a standing ovation at the first preview of Company.

“People see Madame Rose in Gypsy and say, ‘It’s your mother,’ but it wasn’t.”

Sondheim grew up on the Upper West Side, the only child of Herbert, a dress manufacturer, and Etta, who designed the dresses. He said that he did not remember feeling lonely, but noted that when his parents divorced when he was 10—Herbert left Etta, nicknamed Foxy, for another woman—“life became unpleasant and scarring.”

Mother and son moved to Pennsylvania. “I felt unhappy. She was difficult. She was traumatized by my father leaving and took it out on me: not an uncommon situation, the overbearing, grasping, voracious mother who both loves and hates her child,” Sondheim told me. “I’m afraid my mother never loved me. I don’t think she wanted children. She was a career lady. I think I was an accidental birth.

“She said my father had forced her to have two abortions. Since she was a compulsive liar I don’t believe that, but I’ll bet the basis of truth was that she didn’t want a baby. She was certainly no mother to me when they were married. My father was more of a father, he took me to ball games. I think he loved me.”

Sondheim told me his father had sought custody of him, but was refused because he had left his wife for another woman. “My mother had no time for me, but the minute my father left she focused on me because she needed someone to beat up.”

“Many people have difficult relationships with their parents,” he told me in 2015. “People see Madame Rose in Gypsy, and say ‘It’s your mother,’ but it wasn’t.”

Later, his mother expected Sondheim to support her. Did he mind that? “My analyst once asked that and I thought, ‘I guess I do.’ She bled me for as much money as she could. She also stole from me.” Once, when she was about to have surgery, she sent Sondheim a letter saying that her one regret was giving birth to him. There was no reconciliation before her death “She was in a nursing home the last few years. I went a couple of times a year.”

Film, rather than theater, first fascinated him. Aged 10, he became friends with Jamie Hammerstein, son of Oscar, the composer who became Sondheim’s “surrogate father” and mentor. “Everyone forgets Oscar was an experimental playwright. Everyone forgets that Oklahoma was experimental. It didn’t sell out on opening night. West Side Story was experimental, but if it had been a disaster I’m not sure I wouldn’t have slipped back into something comfortable.”

Sondheim’s ambition was to see his name on a marquee, “as proof of my existence.” This happened with West Side Story. “I saw it, thought ‘Oh my God,’ then ‘Now what?’ ” Some of his musicals, particularly Sunday in the Park with George, and his books are about artistic creation. “I have German blood in me. I like order. I tend to be a conservative artist, then I instinctively go for something outré and pull back. My collaborators push me towards the experimental.”

Arthur Laurents, “a serious playwright with a capital P”, and Hammerstein told him to “be specific, not general. Oscar said to write things as I saw them. When I took him my first musical he said, ‘You’re imitating me. Have the courage to be yourself.’ That was a good thing to tell a 15-year-old. It was the seed he planted, which flowered, then covered my life.”

When a customs form asked where he lived, Sondheim told me, he would like to write “the past.” The effects of his upbringing meant he never saw himself as famous, Sondheim added. “I have no sense of myself that way. That’s not modesty. It’s lack of awareness. When people would shake my hand and their palms were wet I would think, ‘What’s wrong with you?’ It’s also because my mother convinced me I was a piece of shit and that lasts. My father would say I’m the best.” The effects of both “prevented me being egotistical.”

This reporter asked if he had ever been depressed. “My general tenor is slightly below the medium line.” His father worked from 14 “and always expected to be bankrupt, no matter how successful he got—it gave him a slightly depressive air, I inherited that from him.”

Sondheim only became “seriously depressed” once, after recovering from a heart attack in 1979. “I got home, was starting to recuperate, then one morning thought, ‘I don’t want to live.’ I guess it was a delayed reaction to the heart attack. The next day I woke up perfectly fine.”

Sondheim came out in his forties. “In my generation people didn’t talk about it. The awareness wasn’t there and I was a late bloomer sexually.” He said he had not formed many relationships, elaborating: “I didn’t fall in love till I was 60. I’ve always enjoyed solitude. It is received wisdom to want somebody or want to be with somebody, but I didn’t until I met Peter [Jones, a dramatist], and if I hadn’t met him I would have gone on perfectly fine.”

He and Jones were together for 10 years. “We are very close friends. He is very happy with his partner,” said Sondheim, who told me he was very happy with his partner, later-husband Romley. “I would miss it [love] if it wasn’t there. But I don’t imagine what life would have been like had I been with someone in my twenties. There wasn’t that yearning.”

“It’s having somebody in your life who enriches you,” Sondheim said of Romley, “somebody who doesn’t let every day be the same day, somebody who forces you to go outside of yourself.” The age gap between him and Romley, then 33, was “an interesting deal,” he told me. “The kinds of music I grew up on are entirely different to his. Although he loves my kind of music, I do not share his taste for contemporary pop music.”

On the 50th anniversary of the Stonewall Riots in 2019, this reporter asked Sondheim by email: “When and how did you first hear about the the riots, what did you make of them; what was their significance for you; how far had LGBT people come in the last 50 years; what would you like to see, LGBT-wise in the next 50 years?”

Sondheim’s response: “Answering those first three questions smacks too much of pontification for me, but I certainly have an answer for the fourth: I’d like to see the term LGBT disappear from the English language.”

“I’m writing very slowly. It’s hard to get back on the bicycle.”

In 2012, Sondheim showed me the room where he composed. There were awards on a mantelpiece, a MacBook Pro on a day-bed, a frayed dictionary on a lectern, a line drawing of Sondheim, a collection of brass letter “S” ornaments and a stained-glass window looking out on communal gardens surrounded by skyscrapers. A block of stone carried the epigram: “Nothing is written in stone.” On a black piano was sheet music with crotchets, quavers and phrases in pencil.

He was then working on All Together Now, which he was composing with David Ives, playwright of the Broadway hit Venus in Fur. He began working on it in 1991; similar in structure to Sondheim’s Merrily We Roll Along, it follows the story of a relationship backwards: from the present to the first meeting.

“I’m a procrastinator,” Sondheim said. “We’ll write for a couple of months, then have a workshop. It seemed experimental and fresh 20 years ago. I have a feeling it may not be experimental and fresh anymore.” In 2015 he was still writing it, telling me, “If I’m lucky I’ll finish it. I don’t see it as my final piece, but there can’t be that many left. It takes a long time to write them.”

Sondheim was a winner of an Oscar, multiple Tonys and Grammys. His beloved black standard poodles Addie and Willie, named after characters in Road Show, were at his feet. “Willie’s a lovebug, Addie’s a predator. Anyone even smelling of food is in danger,” he told me in 2015.

“I’m writing very slowly. It’s hard to get back on the bicycle,” he said. I have spent the past four years writing books [Finishing the Hat and Look, I Made a Hat], so I’m rusty,” Sondheim said. “As you grow older your energies deplete. Only supreme geniuses like Stravinsky and Picasso worked into their eighties and nineties with vigor and freshness. Look at George Bernard Shaw’s later plays: it’s like, ‘Shut up and lie down.’”

Sondheim called his beautiful home “the house that Gypsy built,” referring to the hit musical for which he wrote the lyrics. For a while, Katharine Hepburn had been his “very difficult” neighbor, complaining about the noise as he sang, composing Company.

When her fireplace belched smoke into his house, she charged him half the repair bill. One day, in the gardens hr told me as we stood outside looking at her one-time home, he glanced up and saw Hepburn looking out of a window. “Behind her was the shadow of a man hanging up his trousers. He came forward and put his arms around her waist. It was Spencer Tracy.”

The beats the interview that day were like his musicals and songs—lush but complex, peppy but difficult, playful and painful. His works burrow far deeper into human emotions—with inventive meter, language, and score—than musicals traditionally do.

He strongly denied his characters and stories sprang from his life. “No. These characters have been created by a playwright. The discovery Schubert was a homosexual has led people to look for clues in his music. They look for clues in mine. It’s nonsense, but it helps people navigate through the mysterious shoals of creativity.”

Sondheim thought that some of his shows had been “unfairly maligned”, particularly Merrily We Roll Along, which received brickbats at its premiere in 1981. “It was perceived as a bigger failure than it might have been,” Sondheim said. “When a show is a failure the first time, it is never forgiven, even though we did a lot of work on it.” For every good review “there’s one that says you’re a piece of shit.”

Sondheim’s online 90th birthday celebration was sheer joy for any musical theater fan. As well as Streep, McDonald, and Baranski, Lin-Manuel Miranda sang “Giants in the Sky” from Into the Woods, Josh Groban “Children Will Listen” from Into The Woods and “Not While I’m Around” from Sweeney Todd, Lea Salonga “Loving You” from Passion, Laura Benanti “I Remember” from Evening Primrose, Michael Cerveris “Finishing the Hat,” and Linda Lavin “The Boy From…”

Patti LuPone sang “Anyone Can Whistle,” and finally Bernadette Peters sang, a cappella, “No One Is Alone” from Into the Woods. As she said in closing, “That might be the perfect song right now.”

At nearly 11:30 p.m., host Raúl Esparza addressed viewers about what he saw as the key to Sondheim’s brilliance. “He never stops trying,” Esparza said, adding that if no work of art is ever finished the creative process is also in perennial flux, and so “everything is worth trying… That’s the biggest thing I know about Stephen Sondheim. You keep going on. You keep moving on.”

The encore was “I’m Still Here” from Follies, as sung by a multitude of Broadway performers including Tony winner André De Shields.

The celebration emphasized that which Sondheim kept returning to in our conversations and in his work: living and working with the hat. How he created was illuminated in two books, Finishing the Hat and Look, I Made a Hat. The “hat,” first referenced in Sunday in the Park with George, was a metaphor for the joy of artistic creation.

“If you’re writing experimental work, you can’t expect to be popular, in the sense of having large audiences,” he told me. “Very few shows of any real freshness are hits. The most popular work is not the best work: that’s true of 500 years of Western theatre… When people ask would I like to write a blockbuster, my answer is, ‘Providing I don’t have to sign my name to it.’”

However, these atypical works of musical genius, these alluring, askew diamonds, were hits, and are now classics. However, Sondheim denied that he had set out to challenge the traditional musical form.

“Never consciously,” he insisted to me. “I just wanted to write something I haven’t seen before. Follies is a dour, experimental work. The nun doesn’t escape from the Nazis in the end.” West Side Story, for which he composed the lyrics (his big break), and Gypsy were not considered successful until hit movies were made of them, he said. “They made their money back, which is my definition of a hit. A Funny Thing Happened on the Way to the Forum was my biggest hit.” He wrote music and lyrics but not the book. “That was experimental but in the tradition of vaudeville, which the audience latched on to. I hardly consider myself a starving artist. I’ve made a very good living, just not a blockbuster one. I don’t have a private jet.”

In 2015, he spoke of his pleasure of still writing, still creating. “Then you think of the other things. How will it be received? Will people be disappointed? Do you have any fresh ideas left? All the self-doubt...and then when you’re finishing the hat”—he smiled—“it’s really good.”

Sondheim, like his musicals, could surprise. When we met in 2012, after a deep and candid conversation, he ended our interview just as his musicals sometimes jolted audiences, with a rug artfully pulled out from under feet.

“When you get to a certain age they give you a lot of cut glass,” he said of his many gongs. “The only awards that mean anything are the ones that come with cash.”

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