The Bard of Ambivalence

A playlist for Stephen Sondheim, 1930-2021

Max Freedman
December 3, 2021
Stephen Sondheim in 2004.
Charles Krupa / AP File

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WHEN THE NEWS BROKE last week that Stephen Sondheim had died, I was grateful to be with my parents. Musical theater is the family business—my dad writes musicals, my mom acts in them, and I used to do both. Much has been written about Sondheim’s measureless impact on the art form, but over the last few days I’ve been thinking more about Sondheim’s impact on my life.

“Stephen Sondheim Taught Me How to Be a Person,” wrote Michael Schulman, and that did not sound like hyperbole to me. Nor did this, from John DeVore: “Sondheim was the first adult who told me the truth. He told me the truth with wit and honesty. He didn’t bullshit me. Sondheim didn’t tell me everything was going to be okay. He didn’t know. No one does. Life is sad and beautiful and so was his work.”

I don’t begrudge anyone who’s Not Into Musicals; you may have met some annoying theater kids at an impressionable age, or you may think musicals only paint in primary colors: big, loud, uncomplicated feelings. But Sondheim was the bard of ambivalence. “Ambivalence is my favorite thing to write about,” he told his biographer, “because it’s the way I feel, and I think the way most people feel.” He taught me that ambivalence is not the absence or avoidance of emotion, but the crashing together of tidal waves of different emotions: hope and fear, desire and regret, clarity and confusion, love and anger, joy and pain. He was the first and best dialectical thinker in musical theater.

If you’re new to Sondheim, where should you start? Into the Woods is the gateway drug for many, for good reason; it masquerades as a (mostly) child-friendly mashup of fairy tales until the apocalyptic second act, and the superlative original 1987 production was filmed for PBS.

My entry point, at the other end of the spectrum of child-friendliness, was Assassins. So that’s where I start my memoir-via-Sondheim playlist. Listen along if you can.

The Los Angeles Repertory Company’s 1994 production of Assassins. Max Freedman’s mother, Jean Kauffman, is second from right.

Assassins, “Everybody’s Got the Right” and “Gun Song”

Assassins is an audacious satire, a musical revue starring the motley crew of people who have tried (some more successfully than others) to kill a president of the United States. When I was six years old, my mom played Sara Jane Moore, would-be assassin of Gerald Ford, in the show’s Los Angeles premiere. I spent so much time at rehearsal that I was the production’s unofficial mascot.

The show begins at a carnival (rigged games, rigged country) with “Everybody’s Got the Right,” a straight-faced salute to the American Dream made terrifying by who’s singing it:

Everybody’s got the right to some sunshine
Not the sun but maybe one of its beams
Rich man, poor man, black or white
Pick your apple, take a bite
Everybody just hold tight to your dreams
Everybody’s got the right to their dreams

While my mom was performing in Assassins, I auditioned for a kids’ theater production of Annie. As I remember it, every other kid sang “Tomorrow.” I sang “Everybody’s Got the Right.” And why not? This belongs to a genre of Sondheim song: out of context, straightforward, even anthemic; in context, haunting. (See also: “Our Time” from Merrily We Roll Along.)

Gun Song” is Sara Jane Moore’s big number, shared with Leon Czolgosz, the steelworker and anarchist who killed President William McKinley in 1901. Moore is played mostly for laughs—looking for a gun in her purse, she pulls out a shoe instead—but Czolgosz is deadly serious. He sings:

A gun kills many men before it’s done
Long before you shoot the gun
Men in the mines and in the steel mills
Men at machines, who died for what?
Something to buy—a watch, a shoe, a gun
A thing to make the bosses richer, but
A gun claims many men before it’s done
Just one more...

Assassins plays in the space between the idea of America and the ugly reality, and shows how easily America’s professed ideals can twist into violence. Young as I was, I credit this unlikely musical with profoundly shaping my politics.

Company, “The Ladies Who Lunch”

When I was twelve, I went to sleepaway camp for the first time. It was only four days, but I was really nervous. As we drove to camp, my dad put on “The Ladies Who Lunch” and we sang along. We timed it so that we’d be screaming “Rise! Rise! Rise!” just as we pulled into the parking lot.

Why did I identify with this song? Joanne is a woman of a certain age who sits at the bar, drinking, observing, and drinking. “The Ladies Who Lunch” is her brilliant and vicious taxonomy of other women whom she disdains: the ladies who lunch, the girls who play smart, the girls who play wife. But she reserves her most withering scorn for herself:

And here’s to the girls who just watch
Aren’t they the best?
When they get depressed
It’s a bottle of Scotch
Plus a little jest
Another chance to disapprove
Another brilliant zinger
Another reason not to move
Another vodka stinger!
I’ll drink to that

Whether I realized it or not, by this time I had already learned to be a Joanne (minus the liquor). I could never really figure out how to fit myself into the types or groups that seemed available as a boy in the ’90s, so I watched and mocked and disapproved and was no happier for it.

I hear echoes of Joanne in the Witch from Into the Woods, who sizes up humanity thus:

You’re so nice
You’re not good, you’re not bad, you’re just nice
I’m not good, I’m not nice, I’m just right
I’m the Witch
You’re the world

The Witch may be right, but her bitterness is a dead end: at the end of “Last Midnight,” she gives up—on the world, on herself, on the show. But Joanne, by the final verse of “The Ladies Who Lunch,” arrives at a more generous place. Sarcasm gives way, at least for a moment, to recognition.

So here’s to the girls on the go
Everybody tries
Look into their eyes
And you’ll see what they know:
Everybody dies
A toast to that invincible bunch
The dinosaurs surviving the crunch
Let’s hear it for the ladies who lunch
Everybody rise!

Also, the song absolutely slaps and Elaine Stritch is the fucking best.

Sweeney Todd, “Epiphany” and “A Little Priest”

My version of a goth phase was Sweeney Todd.

There’s a hole in the world like a great black pit
And it’s filled with people who are filled with shit
And the vermin of the world inhabit it
But not for long…
They all deserve to die.

At the end of Act 1, in a murderous, misanthropic aria, the Demon Barber decides that if he can’t have his revenge, he’ll kill as many Londoners as he can. His landlady and admirer, Mrs. Lovett, has the charming notion that she can cover Sweeney’s tracks and save her own business by baking his victims into meat pies.

What follows is “A Little Priest”: seven minutes of puns about eating people, which I thought was absolutely the funniest thing in the world when I was 14. (I briefly went around with my Discman trying to evangelize for Sweeney and Sondheim.)

But the song is also a good example of how most Sondheim songs are doing at least five things at the same time: Sweeney is discovering a creative outlet for his grief and rage; Mrs. Lovett is rejoicing that the emotionally unavailable man she’s wanted for years suddenly seems to want her back; we know this is headed for tragedy—not just because they’re about to start a killing spree, but also because Sweeney is using Mrs. Lovett as a means to his bloody ends, which she can’t (or won’t) see.

All that, plus political commentary:

The history of the world, my love
Is those below serving those up above
How gratifying for once to know
That those above will serve those down below

And most of all, jokes! So many jokes. I won’t spoil them, just listen—or watch.

A Little Night Music, “Now”

Fredrik Egerman is a middle-aged lawyer in turn-of-the-century Sweden, recently wed to a 19-year old; they have yet to consummate the marriage. As his young wife rambles about her day, he retreats into his mind:

Now… as the sweet imbecilities tumble so lavishly onto her lap
Now… there are two possibilities, A) I could ravish her, B) I could nap

He continues in this mode, methodically considering various approaches to seduction, the logistics of each approach, and the possible consequences. Finally, exhausted, he decides he might as well nap. (Once Fredrik is asleep, we hear Anne’s point of view on the same scene.)

The icky circumstances notwithstanding, I have never heard a song that better captures the mechanics of overthinking, the paralysis of analysis. I felt so understood by this song, I insisted on singing it for a high school choir concert, which in retrospect was hilariously inappropriate.

(See also: “On the Steps of the Palace” from Into the Woods)

Sunday in the Park with George, “Move On”

Move On,” from a different show written a decade later, feels to me like a direct answer to Fredrik-style indecision. These words have been there for me when I needed them, many times.

I chose and my world was shaken
So what?
The choice may have been mistaken
The choosing was not
You have to move on

This song goes near the top of a list called “songs I can barely listen to without completely falling apart.” This list also includes “Sunday” (Sunday), “Good Thing Going” (Merrily We Roll Along), and “Not a Day Goes By” (ditto). I have nothing smart to say about these songs, just a deep well of feeling, and from me that is the highest praise.

West Side Story, “Gee, Officer Krupke” / Pacific Overtures, “Please Hello” and “Someone in a Tree”

Though I have careered from career to career—as a playwright, a teacher, now a journalist—I’ve spent most of my working life trying to do the same thing: make complicated systems and histories clear and entertaining. Sondheim was a genius at this.

Exhibit A: “Gee, Officer Krupke.” That this remains, more than 60 years later, such a succinct indictment of everything we call the “juvenile justice system,” is incredible and tragic.

Exhibit B: “Please Hello,” an excellent primer on Western imperialism in 19th century Japan. A series of diplomats (played by Japanese actors in ridiculous costumes and accents) make escalating demands in musical pastiches: Sousa march for the Americans, Gilbert & Sullivan patter for the British, a clog dance for the Dutch, a dirge for the Russians, a can-can for the French. It’s the most fun you’ll have learning about international trade history, I guarantee it.

Exhibit C: “Someone in a Tree,” probably the only song about historiography written for musical theater until Lin-Manuel Miranda’s recent homage “The Room Where It Happens.” The subject matter of both songs is a meeting behind closed doors that will determine the course of world events. Whereas in Hamilton, this meeting is reconstructed out of gossip by the show’s famous antihero, Aaron Burr, “Someone in a Tree” is more modest and unexpected. The old man can’t remember; the boy in the tree can see but not hear; the warrior under the floorboards can hear but not understand. The song is small and frustrating, in a way, but also ecstatic and sweeping.

Sunday in the Park with George, “Finishing the Hat”

When Sondheim published his collected annotated lyrics, he took the titles for both volumes from this song, which is simply the best ever written about the exhilaration and the ache of making things alone in your room. (The more I make things alone in my room, the more I feel this song. It grows with you.)

Finishing the hat
How you have to finish the hat
How you watch the rest of the world from a window
While you finish the hat
Mapping out a sky
What you feel like, planning a sky
What you feel when voices that come through the window
Until they distance and die
Until there’s nothing but sky

Like Into the Woods, the original Broadway production of Sunday in the Park with George was filmed for PBS. You can watch it on YouTube and you should.

Anyone Can Whistle, “Anyone Can Whistle”

I was out for a walk with my mother and grandmother when we got the news about Sondheim’s death. My grandmother is 98 and has dementia. We sat in the sun near her apartment and my mom and I sang this to her, a song that is and is not about learning to whistle.

What’s hard is simple
What’s natural comes hard

My grandmother no longer knows how to swallow a pill. Just about everything “natural” is hard for her. “Anyone Can Whistle” is not about dementia, but those words hit me differently that day.

Sondheim was a brilliant and precise dramatist: in the best of his work, every word, every note, every chord is telling you something about that character and that moment in that story. And yet, I hear him everywhere I go. Whenever I eat greens or figs, have an egg roll, or have some tea, I think about him. I discuss him with my shrink. Day after day after day after day, he gives me more to see. I’m so lucky, I feel like crying.

In other words: we die, but we don’t.

Max Freedman is an audio journalist, educator, and theater artist based in Brooklyn. He is a co-creator and producer of the podcasts School Colors and Unsettled.