Originally published in NYT Style Magazine on October 16, 2017

Sondheim: I hope you don’t mind doing this upstairs, I’m feeling a bit under the weather.

It’s July 2017. We are on the second floor of Stephen Sondheim’s Midtown Manhattan townhouse, and he’s nestled on his writing couch. There’s a famous picture of him reclining in this very spot from 1960: young Sondheim staring intently at a pad of paper, Blackwing pencil at the ready, framed by two windows. His right hand on his face, deep in thought.

Sondheim: The writing’s not going well today.

Nearly 60 years later, Sondheim is on the same couch. He is 87 years old. He’s wearing his rumpled-writer T-shirt and sweatpants, he’s got a sour stomach. He is writing a new musical with David Ives for the Public Theater, an adaptation of two films by the late Spanish director Luis Buñuel, and he’s staring down a deadline. And here I am, interrupting his writing day for this interview.

It’s hard to overemphasize Sondheim’s influence on American musical theater. As a young man, he was mentored by Oscar Hammerstein II of Rodgers and Hammerstein, the songwriting duo who revolutionized musicals with “Oklahoma!” in 1943. Rodgers and Hammerstein wrote fully integrated songs that advanced the plot and revealed hidden depths in their characters; in their hands, musical theater matured into a storytelling art form. Sondheim built on Hammerstein’s innovations by experimenting relentlessly with subject matter and form: from his early lyrics for Leonard Bernstein’s music in the seminal “West Side Story” (1957) and for Jule Styne’s music in “Gypsy” (1959) to more than 50 years’ worth of scores that have pushed the boundaries and subject matter of musical theater in every conceivable direction. He is musical theater’s greatest lyricist, full stop. The days of competition with other musical theater songwriters are done: We now talk about his work the way we talk about Shakespeare or Dickens or Picasso — a master of his form, both invisible within his work and everywhere at once.

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A tabletop at Sondheim’s Connecticut home with an array of games and puzzles — a log-shaped box filled with dominoes, a deck of cards and ivorine word cubes — “so people play with things instead of smoking,” he says. Credit Colin Dodgson

Sondheim was one of the first people I told about my idea for a piece about Alexander Hamilton, back in 2008. It was in this townhouse, on the first floor. I’d been hired to write Spanish translations for a Broadway revival of “West Side Story,” and during our first meeting he asked me what I was working on next. I told him “Alexander Hamilton,” and he threw back his head in laughter and clapped his hands. “That is exactly what you should be doing. No one will expect that from you. How fantastic.” That moment alone, the joy of surprising Sondheim, sustained me through many rough writing nights and missed deadlines. I sent him early drafts of songs over the seven-year development of “Hamilton,” and his email response was always the same. “Variety, variety, variety, Lin. Don’t let up for a second. Surprise us.”

Back to the present day. “Hamilton” is off my desk, and Sondheim’s desk is full.

Miranda: How do you clear your desk and write the next thing?

Sondheim: Well, I collaborate with people. My spark often comes from collaborators. You know, I go to John Weidman1 and say, “Let’s write something else, you got any ideas?” Whatever it is. I mean, I’m a collaborative animal.

Miranda: I’m the same way, except my collaborator is Tommy Kail2.

Sondheim: I need the spur. And the spur and the boost comes from somebody else, generally. Rarely, only in the case of “Sweeney”3 did I come across something myself and think, “Oooh.” Oh, no, and “Passion.”4 Those are the two.

Miranda: And “Sweeney” was the one where you were working from the original text and said, “I need a book writer,” right?

Sondheim: Yeah. I’d been working from a little Samuel French-type version.5 I was up to Page 8 in Bond’s script, which is, I guess, the marketplace scene,6 and already it was an hour and a half long. I thought, “This is not going to work because I don’t know how to cut, really.” I mean I do, but I don’t. That’s why I got Hugh Wheeler,7 because he was born in England, he was the son of a bankruptcy judge. So he knew something about class structure. And I’d had a good time with him on “[A Little] Night Music.” Also, he’d been a mystery writer, you know. He was one of the most prolific mystery writers in America. He wrote (and co-wrote) under a pseudonym, Patrick Quentin.

Miranda: My favorite thing is bringing the song into the room to my collaborators. That’s my favorite part of the process. Not the writing of it, not even it being done. It’s the moment when I know my collaborators are going to make it better.

Sondheim: That’s my least favorite part of collaboration. Unless I really like what I’ve written.

Miranda: Oh?

Sondheim: Then I want to share it with a collaborator. But no, I don’t get that excitement that you get out of it, presenting it to collaborators. First of all, I only really do it with a book writer. I don’t with a director. I just don’t want to call in a director till it’s ready to present, and that means me and my collaborator. But you know, Lapine8 was the first one who actually made me give him unfinished songs. I never give unfinished songs.

Miranda: Did you find that valuable?

Sondheim: No, not particularly, but it was valuable to him.

Miranda: Well, it’s like being naked.

Sondheim: Exactly, and I don’t really mind that as long as I wash myself.

Stephen Sondheim is featured on one of the covers of T’s Oct. 22 Greats issue. See the other six covers

We move on: What makes a good collaborator?

Sondheim: I like writing with people who make me want to write. And you know, they’re hard to find. I don’t mean for me. I mean for anybody. It’s a marriage, and you want to find somebody who —

Miranda: You’re gonna show up naked sometimes.

Sondheim: You’ve got to have somebody who’ll surprise you and, you know, it’s the old lesson, you’ve got to work on something dangerous. You have to work on something that makes you uncertain. Something that makes you doubt yourself.

Miranda: Talk a bit about that danger and uncertainty.

Sondheim: Well, because it stimulates you to do things you haven’t done before. The whole thing is if you know where you’re going, you’ve gone, as the poet says. And that’s death. That leads to stultified writing and stultified shows.

Miranda: Since “Hamilton,” I have been pitched every historical era.

Sondheim: Of course! And so that’s the one thing you don’t want to do. After “Gypsy” I got nothing but backstage stories and I said, “The only thing I don’t want to write is anything to do with show business.” That’s the only thing.

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Sondheim was one of the first people Lin-Manuel Miranda spoke to about his idea for “Hamilton.” Credit Colin Dodgson

SONDHEIM HAS CERTAINLY followed his own advice in this regard: His choice of subject matter over the last half-century of work demolishes any notions of the kinds of stories musical theater can tell. From a violent barber (“Sweeney Todd” with Hugh Wheeler) to ancient Roman farce (1962’s “A Funny Thing Happened on the Way to the Forum,” with librettists Burt Shevelove and Larry Gelbart) to fractured fairy tales (“Into the Woods” with James Lapine). Within this vast terrain, he and his collaborators have also radically experimented with the musical theater form: See the diptych structure of “Sunday in the Park With George,” also with Lapine, in which each act takes place a century apart, or the unprecedented “Company” (1970), with a book by George Furth, a meditation on commitment and monogamy, which Sondheim describes as a “non-plot” musical.” Here he is, arriving at the form of “Follies,” his legendary 1971 musical with librettist James Goldman about a reunion of retired performers from a 1930s Ziegfeldesque revue: “You start with the subject matter and some content and it takes form. If you’re going to say, ‘O.K., it’s a reunion party,’ well, hello, don’t try to give it a plot. And if you don’t give it a plot, what’s going to hold it together? Uh-oh. That’s what’s dangerous and that’s what’s scary about it.”

We gravitate toward the subject of surprise, both for the audience and for the playwright.

Sondheim: That was a big lesson from Peter Shaffer.9 We went to see a play once about the mad queen of Spain and in the first act there were two rapes, an evisceration, a fire and something horrifying with a child, I don’t remember. And at the end of the first act I said, “This is so much my kind of thing. Why am I bored?” He said, “There’s no surprise.” And I thought, “Put that on your bathroom mirror.” Surprise: if it’s in the lyric, the unexpected word, the unexpected note, the unexpected incident. The unexpected, the unexpected, that’s what theater is about. If you had to patent one thing in the theater, it’s surprise.

Miranda: Can you think of any times you’ve surprised yourself in the writing process?

Sondheim: Oh, come on, as a writer you’re always surprised when you think of the right note or the right word. You think, “Oh, I didn’t know I could — oh, that’s good!” You know, writing’s full of surprises for oneself. It comes with the territory, but this is a different kind of thing. This is surprising the audience —

Sondheim bats the question away. He’s either uninterested in recounting a specific time that he surprised himself while writing, or there have been so many that it’s impossible to pick: It comes with the territory.

Two years ago, I interviewed Sondheim and John Weidman together for a PBS documentary, but my favorite moment from the interview never aired. We were on the subject of “Finishing the Hat” from “Sunday in the Park With George,” one of Sondheim’s most celebrated songs, and maybe the greatest song ever written about the self-induced spell of the creative process.10 In this excerpt from that interview, just as in his work, Sondheim’s collaborator brought out the best in him:

Weidman: Do you remember you called me the night you finished that song?

Sondheim (smiling): Was I excited?

Weidman: You were … beyond excited. I mean, it’s like you needed to call somebody. I may have been number 17 on the list, but I could hear it in your voice, you said, “I just wrote this song.”

Sondheim: Yeah, I remember, I wanted to tell everybody. [Laughs.] I wanted to tell everybody. I was really pleased.

Miranda: I love the story you told about the making of it in your book, about being inspired by a party game you were creating for Phyllis Newman’s party,11 and realizing you’d spent the entire night in a sort of trance —

Sondheim: I started planning that game at 8 o’clock in the evening, and when I looked up, it was 7 o’clock in the morning. I’m exaggerating, but not by much. Time had disappeared. That’s what happens — you must know that yourself. You must know that the great thing about writing and creating is, time disappears. You are in the moment, and the moment can go for eight hours or for two minutes, or whatever, until the phone rings, or you know, you have to go get something to eat.

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A spring-wound solar system model called an orrery, from the late 18th century. Credit Colin Dodgson

PRESENT DAY again — I’m trying to give Sondheim credit for expanding the scope of the American musical, and he is passing on the credit to his mentor Oscar Hammerstein instead.

Miranda: Something that’s so essential about your work is that I think you have expanded the terrain of what musical theater can be. The notion of, “This is a musical, that’s not a musical,” is BS. It’s carried entirely by the passion of the creators.

Sondheim: Yeah, but Oscar invented that with “Oklahoma!” He took a play that was about homosexuality in the West and turned it into a sunny musical. Because he saw something in it that was beyond what Lynn Riggs12 had written, about the opening of territories, the promise of America. He saw that which anybody else reading that play would not have seen.

Miranda: O.K. But it gets back to the notion of, “If I can find myself in the work, others will see themselves.” So it’s about not being afraid of specificity.

Sondheim lights up.

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Sondheim with Willie, one of his two standard black poodles. Credit Colin Dodgson

Sondheim: Absolutely! That’s exactly what he taught me, when he criticized my poetic Hammerstein lyrics when I was starting out.13 He said, “That’s not what you feel. Don’t write what I feel. Write what you feel.” Oh! It had never occurred to me to write what I felt. And Oscar was the one who taught everyone to do that.

Write what you feel. Or as George’s muse, Dot, says to him in “Sunday,” “Anything you do,/Let it come from you./Then it will be new.”

And then for a moment you let in the depth and intensity and range of Stephen Sondheim’s feeling for the past half-century. That Tony and Maria of “West Side Story” first fell in love as Sondheim sharpened his Blackwing pencils, finding the words for their doomed romance at age 25. That Mrs. Lovett of “Sweeney Todd” hatched her diabolical plans from this writing couch as Sondheim talked to himself. That within Sondheim, somewhere, is both Georges Seurat and Fosca, Pseudolus and Mama Rose, John Wilkes Booth and Madame Armfeldt, Charley Kringas and Little Red Riding Hood. He has served up vodka stingers for Joanne (“Company”) and chrysanthemum tea for the Shogun (“Pacific Overtures”). Sixty years of iconic theatrical moments, and they exist as a result of the specific way Stephen Sondheim feels. Line by line, note by note, surprise by surprise.

And if you’re Sondheim, there are days like today, when you feel under the weather and the day is full of distractions. But there are also nights when you write “Finishing the Hat,” and you’re so proud of what you’ve made that you have to call a friend and say, “I just wrote this song.”

What’s important is that Sondheim is still here, staring down another deadline. Starting on a hat. Feeling his way toward the moment when time disappears.

Sondheim: You shouldn’t feel safe. You should feel, “I don’t know if I can write this.” That’s what I mean by dangerous, and I think that’s a good thing to do. Sacrifice something safe.

Variety, variety, variety, Mr. Sondheim. Don’t let up for a second. Surprise us.