Stephen Sondheim has a reputation for being difficult. I have never thought that was entirely fair.
His music can be complex and his musicals rarely offer simple answers, but the emotions underneath them are deeply recognisable. His characters fall in love with the wrong people, struggle to connect, make poor choices and discover that getting what they want does not necessarily make them happy.
That is the thread running through much of Sondheim’s work. The question is where to begin.
You could work through his musicals chronologically, starting with his early work as a lyricist on West Side Story and Gypsy. I would not recommend it. A better introduction is to choose the show that speaks most directly to your own interests, then follow the connections into the rest of his work.
For most people, the best starting point is Into the Woods.
Into the Woods is probably the clearest introduction to what makes Sondheim’s work so rewarding.
Written with James Lapine, it brings together characters from several familiar fairy tales. Cinderella wants to attend the festival. Jack wants his cow to produce milk. The Baker and his wife want a child. Little Red Riding Hood simply wants to reach her grandmother’s house.
Each character enters the woods in pursuit of something. By the interval, most appear to have found it. The second half then asks the far more interesting question: what happens after the wish comes true?
It is funny, accessible and filled with memorable songs, but it also introduces many of the subjects Sondheim returned to throughout his career. Parents and children, actions and consequences, the stories we inherit and the danger of assuming that happiness lies just beyond the next obstacle.
Songs such as “Giants in the Sky”, “No One Is Alone” and “Children Will Listen” work beautifully in isolation. Reading the complete libretto gives them their proper dramatic context and reveals how carefully each song moves the story forward.
If someone asked me to recommend just one Sondheim musical to begin with, this would be it.
My second choice would be Company.
The musical follows Bobbie, a single New Yorker celebrating her thirty-fifth birthday while surrounded by married friends. They are all interested in why she has not settled down. Bobbie is less certain that marriage is something she wants at all.
There is no conventional plot. Instead, the musical is built from a series of conversations, dinners, arguments and encounters that gradually reveal different versions of marriage and commitment.
That structure was genuinely daring when Company opened in 1970. It still feels surprisingly modern now.
It is also home to some of Sondheim’s finest songs, including “Sorry-Grateful”, “The Ladies Who Lunch” and “Being Alive”. Each approaches relationships from a different direction. Marriage can be comforting, irritating, necessary and impossible, sometimes within the same song.
The edition available from Fourth Wall contains the complete revised book and lyrics from Marianne Elliott’s 2018 West End production. That revival changed Bobby into Bobbie and reconsidered several of the relationships around her. It demonstrated how a great musical can change with its audience while retaining the questions at its centre.
If you prefer your musical theatre on the darker side, begin with Sweeney Todd.
Benjamin Barker returns to London under a new name after being unjustly transported. Consumed by what has been taken from him, he begins a campaign of revenge with the help of Mrs Lovett, who runs the pie shop beneath his barber’s premises.
The bodies begin to accumulate. Mrs Lovett, being both practical and entrepreneurial, finds a use for them.
That premise makes Sweeney Todd sound like a piece of theatrical horror, and it certainly delivers on that front. But it is also a tightly constructed tragedy about injustice, obsession and a society that consumes people without much thought for the consequences.
The score is enormous, intricate and often operatic. Hugh Wheeler’s book, however, keeps the story moving with the pace of a thriller. It is one of the best examples of Sondheim’s belief that songs should not pause the action. They should be the action.
For a deeper look at the musical, Stephen Sondheim’s Sweeney Todd: Behind the Bloody Musical Masterpiece traces the show from its nineteenth-century origins through the original Broadway production, its major revivals and Tim Burton’s film adaptation.
Sunday in the Park with George is the musical I would recommend to anyone involved in making things.
Inspired by Georges Seurat’s painting A Sunday Afternoon on the Island of La Grande Jatte, its first act imagines Seurat creating the work in 1880s Paris. George is completely committed to his art, but that commitment leaves very little room for Dot, the woman who loves him.
The second act moves forward a century. Another artist named George faces a different set of creative problems. He knows how to promote his work and speak to potential funders, but is no more certain about what he wants to create.
This is Sondheim’s great musical about art, concentration and compromise. Crucially, it does not excuse George simply because he is talented. The work matters, but so do the people pushed aside in the process of making it.
“Finishing the Hat” is often described as a song about artistic dedication. It is also an admission of failure. George can complete the hat in the painting, but he cannot give Dot what she needs.
That tension is what makes the musical so powerful. It understands both the joy of making something and the cost of allowing the work to become everything.
For Sondheim at his most elegant, read A Little Night Music.
Based on Ingmar Bergman’s film Smiles of a Summer Night, the musical follows a collection of mismatched lovers who gather at a country house. Old relationships resurface, current ones begin to unravel and almost everyone finds themselves pursuing the wrong person.
Much of the score is written in variations of waltz time. The music gives the show an effortless sense of movement, even as its characters become increasingly entangled.
It also contains Sondheim’s best-known song, “Send in the Clowns”. Outside the show, it is often treated as a general expression of sadness. Within the story, it is much more precise. Desirée finally recognises that she and Fredrik have mistimed their chance to be together.
This is one of the reasons I recommend reading complete librettos. Familiar songs regain the characters, circumstances and decisions for which they were written.
I would not recommend Assassins as a first Sondheim musical. I would certainly recommend reading it once you understand the way he works.
Written with John Weidman, the musical brings together a group of people who attempted to assassinate presidents of the United States. They meet in a strange fairground outside ordinary time, united by disappointment and the belief that history has denied them what they deserve.
It is dark, funny and deliberately disturbing. Sondheim uses recognisable American musical styles, then gradually twists the optimism associated with them.
The subject could easily have become a historical parade of villains. Instead, the musical examines grievance, celebrity and the promise that everyone is entitled to become somebody. It does not excuse its characters, but it is interested in understanding the stories they tell themselves.
Assassins proves just how far Sondheim believed musical theatre could go.
Sondheim first became widely known as the lyricist of West Side Story and Gypsy.
It is worth making the distinction that he wrote the lyrics for these shows, not the music. Leonard Bernstein composed West Side Story, while Jule Styne composed Gypsy.
The complete book of Gypsy shows Sondheim developing the sharpness and dramatic precision that would define his later work. The songs do not simply describe how the characters feel. They expose things the characters may not yet understand about themselves.
His first Broadway musical as both composer and lyricist was A Funny Thing Happened on the Way to the Forum.
Loosely based on the Roman comedies of Plautus, it is a fast and unapologetically silly farce. It is useful evidence against the idea that everything Sondheim wrote was serious, intellectual or melancholy.
If you want an overview of his complete career, start with Sondheim: His Life, His Shows, His Legacy.
It covers the major musicals alongside less immediately accessible works such as Anyone Can Whistle, Pacific Overtures, Passion and Road Show. It is extensively illustrated, making it a good introduction to both Sondheim and the productions that first brought his work to the stage.
How Sondheim Can Change Your Life takes a more personal approach. Richard Schoch examines what Sondheim’s characters and songs can tell us about love, ambition, loss and the decisions we make.
For those interested in the actual craft, Sondheim on Music is the deeper choice. Through detailed conversations with Mark Eden Horowitz, Sondheim discusses composition, lyric writing, collaboration and the decisions behind individual songs and shows.
Finally, Everything Was Possible: The Birth of the Musical Follies is one of the best accounts of how a Broadway musical reaches the stage.
Ted Chapin worked as a production assistant on the original production of Follies and kept a detailed journal throughout rehearsals. His account captures the rewrites, tensions, practical problems and last-minute decisions behind a musical now regarded as one of Sondheim’s greatest achievements.
Begin with Into the Woods. It is the most welcoming introduction to Sondheim’s ideas and his approach to storytelling.
Follow it with Company for relationships and modern life, or Sweeney Todd if you want something darker and more dramatic.
Then move to Sunday in the Park with George. Once you understand how Sondheim builds a song around a character’s thoughts, it becomes an even richer piece of writing.
After that, the choice is yours. Try the elegance of A Little Night Music, the difficult questions of Assassins or return to the beginning with Gypsy.
There is no need to admire every Sondheim musical equally. Part of the pleasure is discovering which one feels as though it was written directly for you.
