Stephen Sondheim is often called one of the greatest writers in musical theater history. His lyrics are famously clever, his melodies can be complex, and his shows tackle big, adult ideas: love, ambition, art, regret and revenge. That reputation can make newcomers nervous. Where do you start?
The good news is that Sondheim wrote shows for every kind of audience, from fairy-tale comedies to gothic thrillers. This guide ranks some of his most accessible musicals for beginners, explaining what makes each one a good entry point. Sondheim died in 2021, and his work continues to be revived around the world.
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Before You Start: What Makes Sondheim Different?
Sondheim’s songs tend to reveal character and move the story forward, rather than stop the action for a hit. His lyrics are packed with wordplay, internal rhymes and twists in meaning. His music often uses unusual rhythms and harmonies. The result can take a couple of listens to fully appreciate, but it rewards your attention.
Tip: listen to a cast album before seeing a show. Familiarity makes Sondheim much easier to enjoy live.
1. Into the Woods
Why it’s great for beginners: Familiar fairy tales, plenty of humor and a story that works for families and adults alike.
Into the Woods, with a book by James Lapine, opened on Broadway in 1987. It mixes Cinderella, Little Red Riding Hood, Jack and the Beanstalk and Rapunzel with an original story about a Baker and his Wife. Act One is a comic adventure; Act Two asks what happens after “happily ever after.”
Songs like “Agony,” “Giants in the Sky,” “No One Is Alone” and “Children Will Listen” are among Sondheim’s most loved. A 2014 Disney film is an easy introduction, although the stage show is fuller.
2. Sweeney Todd: The Demon Barber of Fleet Street
Why it’s great for beginners: A gripping, dark thriller with unforgettable music.
Sweeney Todd, with a book by Hugh Wheeler, opened on Broadway in 1979. It follows a barber in Victorian London who returns from unjust exile seeking revenge, and Mrs. Lovett, the pie-shop owner who helps him.
It’s macabre and bloody, but also darkly funny, especially in “A Little Priest.” The score is operatic and thrilling. Tim Burton’s 2007 film is another way in, though it cuts some songs.
Note: Not for young children.
3. A Funny Thing Happened on the Way to the Forum
Why it’s great for beginners: Pure comedy.
Forum was the first Broadway show for which Sondheim wrote both music and lyrics. With a book by Burt Shevelove and Larry Gelbart, it opened on Broadway in 1962. It’s a farce set in ancient Rome, following a clever slave named Pseudolus trying to win his freedom.
Songs like “Comedy Tonight” set the tone. It’s fast, silly and very different from Sondheim’s later work, making it a fun, low-pressure start.
4. Company
Why it’s great for beginners: Relatable themes about relationships and adult life.
Company, with a book by George Furth, opened on Broadway in 1970. It follows Bobby, a single person in New York, on their birthday, surrounded by married friends. It’s told in vignettes rather than a traditional plot.
Songs like “Being Alive,” “The Ladies Who Lunch” and “Getting Married Today” are famous. Some recent productions have reimagined Bobby as a woman, Bobbie, showing how flexible the show can be.
5. A Little Night Music
Why it’s great for beginners: Romantic, elegant and witty.
A Little Night Music, with a book by Hugh Wheeler, opened on Broadway in 1973. Inspired by Ingmar Bergman’s film Smiles of a Summer Night, it follows tangled romances among a group of characters in turn-of-the-century Sweden. Much of the score is written in waltz time.
It includes Sondheim’s most famous song, “Send in the Clowns,” as well as charming numbers like “A Weekend in the Country.”
6. Sunday in the Park with George
Why it’s great for beginners: For anyone interested in art and creativity.
Sunday in the Park with George, with a book by James Lapine, opened on Broadway in 1984. It’s inspired by Georges Seurat’s painting A Sunday Afternoon on the Island of La Grande Jatte. Act One imagines Seurat creating the painting; Act Two jumps forward to his descendant, a modern artist.
It’s more reflective than other shows on this list, but songs like “Sunday,” “Finishing the Hat” and “Move On” are moving tributes to the creative life.
7. Merrily We Roll Along
Why it’s great for beginners: A clever structure and very catchy songs.
Merrily We Roll Along, with a book by George Furth, opened on Broadway in 1981. It tells the story of three friends in reverse, starting when they’ve drifted apart and moving back to when they first met.
Its songs, like “Old Friends,” “Not a Day Goes By” and “Our Time,” are among Sondheim’s most tuneful. The reverse structure gives it a bittersweet power.
Sondheim as Lyricist: West Side Story and Gypsy
Before writing his own scores, Sondheim wrote the lyrics for two classics:
- West Side Story (1957), with music by Leonard Bernstein and a book by Arthur Laurents. It’s a retelling of Romeo and Juliet set in New York. It has been filmed twice, in 1961 and in 2021, the second by Steven Spielberg.
- Gypsy (1959), with music by Jule Styne and a book by Arthur Laurents. It follows Rose, the ultimate stage mother, and her daughters.
Both are great entry points, since their music is more traditional while Sondheim’s wit shines through in the lyrics.
Shows to Save for Later
Sondheim wrote other remarkable musicals, including Follies, Pacific Overtures, Assassins and Passion. They’re well worth exploring, but many fans find them richer once they already know his style. Treat them as the next step after the shows above.
A Suggested Starter Path
- Start with Into the Woods or West Side Story for familiar stories.
- Move on to Sweeney Todd if you like darker drama, or Forum for comedy.
- Try Company and A Little Night Music for adult relationships and wit.
- Then explore Sunday in the Park with George and Merrily We Roll Along for deeper reflections on art and friendship.
Keep exploring: see our Into the Woods songs explained and musicals like Phantom list.
Want to play these songs on piano? Sondheim’s songs reward close listening — and playing them. From Into the Woods and Send in the Clowns to Being Alive, learning by ear helps the intricate melodies stick. Try Pianoforall, a beginner-friendly course.
Disclosure: affiliate link; Musicals On Line may earn a commission at no extra cost to you.
Where to Listen Legally
- Original Broadway cast recordings of all these shows are on Spotify, Apple Music and other major services.
- Many revival cast recordings are also available, often with fresh orchestrations.
- Film versions of Into the Woods (2014), Sweeney Todd (2007) and West Side Story (1961 and 2021) are available on various streaming and digital platforms, depending on your region.
FAQ
What is the best Sondheim musical to start with?
Into the Woods is a great first choice. It’s funny, familiar and full of memorable songs. Sweeney Todd is another favorite for adults.
Did Sondheim write West Side Story?
He wrote the lyrics. The music is by Leonard Bernstein and the book by Arthur Laurents.
What is Sondheim’s most famous song?
“Send in the Clowns,” from A Little Night Music, is widely considered his best-known song.
Are Sondheim musicals hard to understand?
Some are complex, but listening to the cast album first helps a lot. Shows like Into the Woods and Forum are very accessible.
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