Stephen Sondheim Helped Me See Myself

The legendary songwriter knew that people can have mixed feelings about basically everything

View of American composer and lyricist Stephen Sondheim onstage during an event at the Fairchild The...
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B.D. McClay

I must have been around six when a friend of my parents gave me a VHS tape she’d recorded from PBS, along with a stack of Andrew Lang fairy tale books. She thought I’d like them. On the tape was a musical called Into the Woods. It followed a set of traditional fairy tales (“Cinderella,” “Little Red Riding Hood,” “Jack and the Giant Beanstalk,” “Rapunzel”) and then one new one, about a baker and his wife who are trying to conceive a child. The first act gives each story the traditional fairy tale ending: Cinderella gets her prince, Little Red Riding Hood and her grandmother are saved from the wolf, Jack becomes wealthy and kills a giant; Rapunzel is freed from her tower; the Baker and his wife have a child. In the second act, the wife of the giant Jack killed at the end of his story comes back for justice, though revenge will do too, and everything gets much more complicated.

I’ve often wondered if the woman who gave me the tape ever actually watched Into the Woods, because if she had, I doubt she would have thought it an appropriate gift, but in any case, she was right about my taste. I watched it over and over, the way kids do, and I made my friends watch it, though I don’t remember converting any new fans. Then I forgot about it for years, until, as a teenager with an interest in musicals, I came back to it because I’d heard about its composer: Stephen Sondheim.

This is how I remember it, at least. As Sondheim knew — we don’t always remember things the way they happened.

Much has already been written about Sondheim, who died last Friday at the age of 91. A mentee of Oscar Hammerstein II, the lyricist behind Oklahoma! and South Pacific, Sondheim entered musicals professionally by writing the lyrics for Leonard Bernstein’s West Side Story (1957). In 1962, A Funny Thing Happened on The Way to the Forum, his first musical for which he wrote the music and the lyrics, debuted. From there he’d go on to write musicals that defined and redefined the form: Into the Woods, Sunday in the Park with George, Assassins, Merrily We Roll Along, Company, A Little Night Music, Sweeney Todd, Pacific Overtures, Follies.… The list goes on, if only in the sense that I left one or two off in order to say “the list goes on.”

And much of what’s been written is by people who are better positioned than I am to explain what made Sondheim special, as an artist, a composer, a person; tributes to the cleverness of his writing, the breadth of his subject matter. And things will keep on being written, because he really was special, not just in the wake of his death but for years and decades to come. I’m not going to try to write something definitive or exhaustive, partly because I can’t, partly because I’m not sure anybody can.

Sondheim’s music was, for a long time, like a pair of shoes I’d step into without really being able to wear yet. When I was six I didn’t really have a clue what was going on in Into the Woods — I just liked it. I adored Joanna Gleason’s beautiful Baker’s Wife, who seemed to me, at the time, a kind of height of womanly perfection — beautiful and smart and a little ruthless — and remember feeling dejected when she cheats on her loving husband and dies in the musical’s second half. I didn’t understand why somebody would do something like that, something perverse and self-sabotaging, right after having the child she wanted so badly with the husband she loved so much. I hated that she died. I just wanted her to explain it to me.

Now, I put on the shoes and they fit my feet. Because I know the Baker’s Wife doesn’t really understand why she does it either. Sometimes we do hurtful things to people who love and trust us, and we don’t know why, at the time, or later, or ever. That’s never an excuse, but it is the truth.


Lots of people do not like musicals, the same way lots of people don’t like opera, or ballet. These are art forms that draw attention to their own artificiality, and while you can enjoy them casually, even dipping a toe into their dedicated audience will reveal many people with encyclopedic knowledge of the form’s history and strong opinions, which can be daunting. (Musicals are also associated with over-earnest nervous energy, which doesn’t help them much.)

On the other hand, most people do know and like songs from musicals, which have joined the larger American culture as standards. I suspect that these songs succeed in part because most people can sing them, but also because they are songs that tell stories, and, as such, tend to be complex — funny and sad, heartfelt and distanced. I might never see Anything Goes, the Cole Porter musical that “I Get A Kick Out Of You” comes from, but the song itself has everything I need to know, which is that it’s about loving someone who doesn’t love you, not despite that, but because of it.

Sondheim’s songs — including the ones that have become standards, like “Send in the Clowns” and “Losing My Mind” — have this fundamental complexity, but they have another shared quality on top of that, too. When you listen to a Sondheim number, you feel that the singer is totally embodying whatever is going on with them but also standing slightly outside of it. They are distanced from themselves, don’t quite know their desires, and are often caught between some expression of the idealized past and the more compromised present. Take Company (1970). Single man Bobby is surrounded by coupled friends. Does he want to be coupled up? Sort of. Maybe not. Are his friends’ romantic lives good? Kind of. Company has a bruised romanticism about it. You want to be close to people and you want to be far away. You want to really love somebody, you want to be free to love anybody.

The problem for most of Sondheim’s characters is their own self: their loneliness, their selfishness, their stubbornness, their disappointment in the realization of any given possibility. They love beauty, but they don’t want to love beauty that could love them back. Estrangement, resignation, distance — these are the qualities that make Sondheim’s most memorable songs and characters what and who they are. They know that they’ll survive whatever comes their way, but they have mixed feelings about knowing that.

In these shows, there are very rarely true villains (though there are a few, like the Judge in Sweeney Todd). A lesser artist would have made the Baker’s Wife’s decision to cheat on her husband a moment of liberation from a bad marriage to a boring husband. But part of why it hurts is because we love the Baker, who is neither bad nor boring, and who, in the wake of his wife’s death, gets the musical’s most heartbreaking (and, for my money, best) song, “No More.” These stories still have conflict, but for Sondheim conflict is what happens when one person, one bundle of hope and resentment, runs into another.

In their worst cases, Sondheim’s characters can risk becoming ghosts in their own lives, obsessed with their inability to connect, preoccupied with failure. But Sondheim’s insight partly is that we’re all haunting our own lives, both in the mark our real choices leave and in the possibilities our lives have contained. If we didn’t contain this internal conflict, this multiplicity, we would be something less than human. Saying that the things in life that make us suffer are also the things that bring us joy feels a little trite, but the reason that it feels that way is because it is difficult to really believe. When I listen to Sondheim, I do believe it, at least as long as the song runs.

Sondheim’s ability to observe these qualities in his characters comes from paying sustained and loving attention to others. There’s nothing cold or cruel about it, even when what the characters are saying or doing is degrading or wrong. In an interview with Sondheim from 2009, his fellow composer Adam Guettel referred to Sondheim as “unfailingly honest and extraordinarily kind.” He meant Sondheim the person there — but it’s true of Sondheim the composer just as much. And while I imagine that if I’d never been given that tape of Into the Woods, some parts of me would be much the same, the man who drew the map for me of what it’s like to be a person, who put into expression my private experience, was Stephen Sondheim.

Of course I’ve sometimes wondered if Sondheim’s influence over my life was all benign. Maybe the other me would be cheerier, less conflicted, more driven, and lack the persistent feeling of looking in through the window on herself all the time. I prefer to think not, but who can say? A sentiment I hope he’d have appreciated, if he’d ever heard it.

B.D. McClay is an essayist and critic.