Arts Remembrance: Singing Sondheim — A Personal Appreciation

By Peg Aloi

Stephen Sondheim’s songs told stories about people just trying to be, sung by characters struggling to make sense of a confusing world, yearning to take the next step. But his intricately structured melodies soared and tiptoed and sauntered and sometimes wisely took the long way home.

The late Stephen Sondheim. Photo: Wiki Common

I couldn’t tell you the first time I heard a song by Stephen Sondheim, but I can definitely tell you the first time I sang a song by Stephen Sondheim. I was in ninth grade and just beginning to be involved with performing; then I went on to become a theater major in college, so there you go. I blame Mr. Sondheim. I had sung in the school chorus for years and was very fortunate to have excellent music teachers from grade school onwards. My high school voice teachers were enthusiastic devotees of the latest in musical theater, and arranged for us to take charter bus trips to Manhattan to see the latest hits on Broadway. Before I was 20 I saw the revival of Oklahoma!, 42nd Street (with Jerry Orbach!), Evita (with Patti Lupone! But sadly we missed Mandy Patinkin who had been replaced three days earlier) Dreamgirls (with Jennifer Holliday!), They’re Playing Our Song, and Joseph and the Amazing Technicolor Dreamcoat (also Amadeus with Ian McKellen and Tim Curry, and Vampire Lesbians of Sodom, Off-Broadway). Every outing reinforced in many of my classmates’ minds their desire to pursue a life on stage. For me, the experience of seeing live theater was a separate pursuit, an adventure and ritual. The notion that I might one day stand where those performers stood, sing what they sang, dance and move under those same lights — that was a glittering fantasy.

Still, our teachers and mentors encouraged our dreams. We used to do a summer musical revue that included scenes from four different musicals with solos and choral numbers. My first experience with these shows was a performance of “Comedy Tonight” from A Funny Thing Happened on the Way to the Forum, Sondheim’s 1962 Broadway hit. This number opened the evening and I recall we stepped to the footlight as if we were still getting ready backstage: some had hair in curlers, some faces were only half covered in makeup, some were half dressed. I put a green clay facial mask on my face and sang my heart out. It’s an energetic number and I recall a friend at the time, an upperclassman who was already involved in theater and later became an esteemed Broadway producer, saying to me, “you’re such an energetic little performer!” Well, theater got into my blood and so did Sondheim.

One of the summer revues a couple of years later included Sweeney Todd (The Demon Barber of Fleet Street), fairly new at the time. The show was taking the world by storm (neck and neck with Andrew Lloyd Webber’s Evita), thanks to powerful performances by the likes of Angela Lansbury and Len Cariou. I was chosen to sing “By the Sea” as Mrs. Lovett. It was a challenge for a high school girl to play a middle-aged woman, just as it was for an American to sing in a Cockney accent. But the biggest challenge was the song itself. Even a chipper upbeat number like that reflected Sondheim’s knack for creating melodies that were slightly unexpected, intricate, and rather tricky to sing. But I somehow pulled it off, relishing how I could emphasize characterization with my lower vocal register and hit the higher notes without going sharp or flat. That was a demand that Sondheim relished in his creations for female singers: melodies that rode perilously close to the “break” between chest voice and head voice, songs that expressed plot moments brimming with suspense and danger. Sweeney Todd was a show unlike anything Broadway (or London) had ever seen: murder, depravity, insanity, and plenty of blood, yet awash with humor and pathos.

That autumn, our regular music and voice teacher went on sabbatical for the school year. His replacement had been teaching our class in music history and literature. She spent at least a week playing us Sweeney Todd‘s entire cast album, commenting, analyzing, and discussing the lyrics and score. It was quite a mature text to be sharing with high school students, and we were captivated. I’ve always thought the strongest and most thrilling musical portions of the musicals were in the choral numbers, which featured such stunning, harrowing lyrics as “swing your razor wide, Sweeney/hold it to the skies/freely flows the blood of those who moralize.” I was very disappointed when Tim Burton’s film version omitted  the choral numbers, especially the one that repeats every time Sweeney murders someone. They were an effective marker of his intensifying rage and obsession.

While I enjoyed Johnny Depp and Helena Bonham Carter in the lead roles of the film, it was fairly obvious to me that Carter’s singing, while perfectly fine, felt somewhat labored, as if she were concerned she wouldn’t get the notes exactly right. Fair enough: these songs were never easy to put across. I recall a college classmate singing “Send in the Clowns” (from A Little Night Music, 1973, later a film starring Elizabeth Taylor, Diana Rigg, and Len Cariou) at a retreat we did for our chamber singers group. She made it sound very easy and natural, but when I tried to tackle the song myself I realized how very difficult it was, especially for a young singer, to deliver the vocal power and world weariness it called for. With his songs that asked so much of singers, Sondheim crafted a musical quest for performers that mirrored the complex trajectories of his characters.

And that was the thing that Sondheim taught me about performing. His musicals were often very adult in their subject matter and expression. Like Company (1970), the show that my college theater department did when I was a sophomore (I didn’t get cast). Here were a bunch of 17- to 22-year-olds playing older married folks and sophisticated young Manhattan singles. There’s an abundance of sexual content in the story, and a certain savvy cynicism to many of the lyrics. The description of New York City in one powerful solo, “Another Hundred People,” still rings true:

It’s a city of strangers, some come to work, some to play.

A city of strangers, some come to stare, some to stay.

And every day some go away

Or they find each other in the crowded streets and the guarded parks,

By the rusty fountains and the dusty trees with the battered barks,

And they walk together past the postered walls with the crude remarks.

And they meet at parties through the friends of friends who they never


Speaking of Company, personally for me the most powerful moment in Noah Baumbach’s 2019 film Marriage Story finds Adam Driver (an actor I’m not usually terribly enamored of) choosing to sing the finale of that musical, “Being Alive” at karaoke. It’s a song sung by Bobby, the main character, whose serial dating feels empty to him as he continues socializing with all his friends, married couples in varying stages of angst. The performance is unironic, Driver’s character slowly feeling more confident as he remembers the lyrics and, perhaps, his performance of this song on stage when he was younger. The film is rumored to be somewhat autobiographical, chronicling the dissolution of Baumbach’s marriage before he started seeing actress/director Greta Gerwig.

In Gerwig’s 2017 film Ladybird there is a sequence where students put on a production of Merrily We Roll Along, Sondheim’s 1981 sleeper about a composer reminiscing on his life, beginning in the present and moving backwards. The actors play older characters who grow progressively younger. Casting and performing this show is a conceptual boondoggle: Do you pick young performers for their spry bodies and tireless vocal chords? Or older performers who offer the life experience and the vocal subtlety necessary to really do justice to the subject matter? Of course, because Merrily We Roll Along revolves around people in the prime of youth, the musical is commonly performed by high schools, a delicious irony that no doubt Sondheim himself must’ve appreciated. For Baumbach and Gerwig, singing Sondheim serves as a rite of passage that every theater kid goes through. The suggestion is that his songs follow us as we mature, seeping into our very bones as we finally, finally begin to understand who these people were and what they were trying to tell us.

It took me a long time to find my voice as a singer, and I don’t think it occurred while I was still in school. But singing musical theater was one of the things that I enjoyed doing most; it’s an art form unlike any other. For me, its combination of purity and boldness is unique. In my senior year of high school my vocal teacher and the music director of our stage productions encouraged me to sing the title song of Sondheim’s Anyone Can Whistle (which premiered on Broadway in 1964). It had a deceptively simple melody but also large octave jumps and chromatic intervals that made the tune vocally difficult. My teacher seemed to think it was well suited to my voice; and maybe he also thought the challenge would do me good. But it was the song’s theme that I think he really wanted me to engage with. It’s just a very simple exploration of what it means to not be able to do something that everyone else can do. About what it means to yearn for things we don’t have, to want to be something that we may never be. But trying to be that thing anyway. Anyone can whistle; that’s what they say: easy! Anyone can whistle any old day, easy. It’s all so simple: relax, let go, let fly! So someone tell me, why can’t I? I’m grateful for that lesson from Sondheim, and so many others. His songs told stories about people just trying to be, sung by characters struggling to make sense of a confusing world, yearning to take the next step. But his intricately structured melodies soared and tiptoed and sauntered and sometimes wisely took the long way home.

Peg Aloi is a former film critic for the Boston Phoenix and member of the Boston Society of Film Critics. She taught film studies in Boston for over a decade. She writes on film, TV, and culture for web publications like Vice, Polygon, Bustle, Mic, Orlando Weekly, Crooked Marquee, and Bloody Disgusting. Her blog “The Witching Hour” can be found at

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  1. JoAnne Pase on November 29, 2021 at 6:38 am

    Well done, Peg. No wonder Seth found you so interesting.

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