We start with "The Ladies Who Lunch" from Sondheim's 1970 musical Company (book by George Furth), which is the show's 11 o'clock number and an emotional hurricane.
The Set-Up: Our protagonist Bobby, who has turned 35 and is terrified of commitment, is out for drinks with the older Joanne, who has been divorced many times and in some ways is an image of Bobby's possible future, hard drinking, cynical and emotionally scarred. As her husband Larry gets out on the dance floor offstage, Joanne sings this song to Bobby.
The Performance: The song has been sung by all the greats, but to my mind there's nobody better than the lady that originated the role, Elaine Stritch. Here she is at Carnegie Hall almost 30 years later (!).
The structure of the song follows a pattern Sondheim uses in a number of his bigger songs--rather than telling a story per se, each stanza provides a different riff on the same theme, in this case, that all those East Side upper class women you see with all their money and opportunity are living lives of emptiness and desperation.
The Storytelling: You could write whole books about this performance and Sondheim's songwriting. But here are three things that stand out to me:
1) You Get More Miles from Going the Opposite Direction
The song is offered as a toast to women, a time for praise. But in fact every single line is a switchblade cut of ironic devastation.
It's so tempting to have characters pour out their hearts. It can feel so cathartic to write that, too. But when characters refuse that call and go the opposite way--speak positively in the face of pain; express loathing through love--it gives them depth, layers, room to move. We are able to get to the insane screaming ending of the piece only because Sondheim allows Joanne to start from such a different, seemingly deached place.
2) Make it Personal
"Ladies who Lunch" is in many ways an observation song. Joanne paints detailed pictures of the horror shows she's witnessed.
But if it were only that, the song probably wouldn't work. Because it's the same thing over and over. At some point, we get it. Who cares?
The reason we stay invested is precisely because Joanne's own internal sense of horror is slowly revealed. Some of that is about performance choices, like the insane scream that Stritch offers the end of the fourth verse, or the way she delivers that last line "Rise!" over and over.
But it's also the fact that Sondheim has her singing "Rise" a hundred times in a row in the first place, like a record that keeps skipping; or the little comments where she lets the irony slip and says exactly what she means--"too busy to know they're fools" (end of stanza three) or that incredible depth charge moment at the end of stanza five: "Look into their eyes and you'll see what they know/Everybody dies."
At this point it's very clear, Joanne is singing from her own experience. The song is doing more than pointed observations; it's this incredible woman's slow motion existential shriek of horror.
The fact that immediately after the song she makes a hard pass at Bobby is the period at the end of the sentence, her latest attempt to escape the nightmare for a moment and feel something.
Patti LuPone in the 2020 (and hopefully 2021) production
3) Let Your Characters Get Ugly
It's so natural as a writer to protect your characters. They're our babies. We want them to be smart, pretty and well taken care of, and so we make things easier on them than they should be, or we try to polish them up and make them look nicer than they are so they won't get picked on at school.
But in practice that's a terrible choice. Protecting your characters makes the stakes low and the conflicts unimportant (or undermined). And allowing your characters to get ugly actually makes them accessible. The audience goes nuts at the end of the song precisely because Stritch was willing to be that vulnerable with us on stage.
