Stephen Sondheim listening to music in the recording control room during the original cast recording of the Broadway musical "Into The Woods" in 1987. (Photo/JTA-Oliver Morris'Getty Images)
Stephen Sondheim listening to music in the recording control room during the original cast recording of the Broadway musical "Into The Woods" in 1987. (Photo/JTA-Oliver Morris'Getty Images)

How Stephen Sondheim helped me find my gay Jewish sensibility

If I had to identify my first self-actualizing gay experience, it would be back in high school in the mid-1970s. A friend and I nervously got in the car and drove downtown to the Chicago Loop for a performance of “Side by Side by Sondheim,” the 1976 musical revue featuring songs from musicals by Stephen Sondheim, who died last week at the age of 91.

The lights dropped and suddenly there were three singers on stage, along with the evening’s host, Cyril Richard. Richard died soon after that performance and, on my second visit, had been replaced by Shari Lewis and Lambchop. Lampbchop stole the show, performing “Little Lamb” from “Gypsy” in a pinspot on an otherwise dark stage.

Before this I’d only caught bits and pieces of Sondheim’s work. I’d heard Judy Collins singing “Send in the Clowns,” I’d seen “West Side Story.” But I already sensed that there was something in Sondheim’s outlook, something in his worldliness and wittiness, that was or was going to be important to me — that in some way was about me. It was what made this excursion both thrilling and risky.

After the show I bought the cast album and listened incessantly until I knew every word, until I could sing the patter from “Not Getting Married” and “Another Hundred People” as fast as anyone. I sat at the piano for hours working through all the sheet music.

And from that point on, Sondheim was in my life. Stopping in England as a 20-year-old backpacker returning from a year at Hebrew University, I had the good luck to see the original London production of “Sweeney Todd.” Many Sondheim moments followed.

When my performing group, the Kinsey Sicks, or “America’s Favorite Beautyshop Quartet,” recorded a loving parody of a Sondheim tune in the mid-2000s, we hoped that he would hear it and enjoy it. (We don’t know if he ever did, and we largely considered ourselves lucky not to have gotten sued.)

RELATED: The last and greatest gift Stephen Sondheim gave us

We all have our Sondheim stories. People’s relationships with his work seem much more personal than anything ever articulated about Rodgers and Hammerstein. Maybe because Sondheim captures something of our human complexity that composers and lyricists before him could not. A Sondheim play is like us — packed full of emotion, equivocation, uncertainty, hope, fear. He reflects back all that complexity. Complicated ideas are tied up in internal rhyme sitting atop what is often unsingable music that can break the best of singers.

Sondheim’s urban, urbane remove leaves some people cold; to them it reads as plain snobbiness. But there is something so painful and (to me) familiar in his reserve that seems to speak to me directly. It is not just a theatrical affectation. It is Sondheim’s situation; it pains him and interests him. There’s something clearly gay in it — or 20th-century gay in it — this vantage point of being an observer of the action, wanting to participate, but not knowing how to take that risky first step. Or knowing too much to do so.

That sense of in it but not of it is not just a gay thing, but a Jewish thing. American Ashkenazi Jews of the mid-20th century, the children or grandchildren of immigrants, struggled daily to assimilate into a culture that wasn’t ours. The gap between the desire to belong and actual belonging is itself the source of so much Jewish humor. Jewish writers and artists and composers wielded tremendous influence, forging many elements of what Americans came to perceive as American. But the irony is that creating American culture did not necessarily allow Jews to relax into it. On the contrary, authorship meant having a burdensome awareness of the artifice of American culture.

This Jewish predicament, this gay predicament, is reflected and refracted throughout Sondheim’s work. (Sondheim himself was both Jewish and gay.) We see in his writing our deep longing to let go and belong, even while questioning the authenticity of the thing we want to belong to.

This difficulty in knowing how to simply be natural is not just a cultural phenomenon but a spiritual one. We live in limited bodies, forced to connect through language alone. We can never fully understand each other. We know we are made of carbon. We are part of the evolutionary unfolding of the universe, but we find ourselves painfully separated from all other life on the planet. We might intuit that we are part of the same Divine Oneness, but we live our lives in separateness. We feel out of step, out of alignment, no matter how busy and clever and productive we are.

The title song from “Anyone Can Whistle” contains a little of Sondheim’s medicine for this. Part lament and part prayer, the singer asks for witnessing and for companionship, as a first step in dissolving the boundaries of these bodies and these egos. The song is a prayer for all of us gay or Jewish or overthinking people imprisoned in the safe refuge of our heads. A prayer that we might give up the fight and crack open at last.

Anyone can whistle, that’s what they say. Easy.
Anyone can whistle any old day. Easy.
It’s oh so simple: Relax! Let go! Let fly!
So someone tell me why can’t I.
I can dance a tango. I can read Greek. Easy.
I can slay a dragon any old week. Easy.
What’s hard is simple. What’s natural comes hard.
Maybe if you show me how to let go,
Lower my guard,
Learn to be free.
Maybe if you whistle, whistle for me. 

Thank you, Stephen Sondheim, for helping us let go and be free.

Reb Irwin Keller
Rabbi Irwin Keller

Rabbi Irwin Keller has served Congregation Ner Shalom in Sonoma County since 2008. He blogs at