Five Best Stephen Sondheim Musicals

Updated on February 8, 2018

Facts About Stephen Sondheim

Did you know...

  • He was mentored by Oscar Hammerstein II.
  • He was Katharine Hepburn's neighbor for many years.
  • He has won more Tonys than any other composer.
  • He shares a birthday with Andrew Lloyd Weber.
  • He cameoed in the musical movie "Camp" as himself.

The Musicals of Stephen Sondheim

If you're in love with musical theater, hearing Stephen Sondheim's name probably makes you smile, and lyrics might start running through your mind. And even if you've never heard of Sondheim, you probably know his work--he wrote the lyrics for the musical West Side Story, and was the composer and lyricist of Sweeney Todd: The Demon Barber of Fleet Street.

It's not an exaggeration to say he revolutionized musical theater--he took the stage from a world of frothy, fluffy musicals (think Oklahoma!) to musicals of dark, gritty complexity, where main characters weren't always upstanding and the ending wasn't necessarily happy ever after.

Read on for the five best musicals of Stephen Sondheim.

Sweeney Todd: The Demon Barber of Fleet Street

Stephen Sondheim's "Sweeney Todd: The Demon Barber of Fleet Street" is a dark, violent musical that encompasses rape, murder, and cannibalism--and described as such, it doesn't sound particularly watchable. However, it's one of Sondheim's best works, with a complex score and masterfully intelligent lyrics--and despite its dark subject matter, it includes one of his funniest songs, "Have a Little Priest."

In "Sweeney Todd," Benjamin Barker is a barber happily living in London with his wife and young daughter, Johanna. When a lecherous judge decides he must have Barker's wife, he sends Barker to prison on a pretext; the wife poisons herself after the judge rapes her, and the judge takes Johanna as his ward.

Years later, Barker returns, having reincarnated himself as Sweeney Todd and hell-bent on getting revenge. With the help of the darkly likeable but clearly psychotic Mrs. Lovett, he begins plotting his vengeance and eventually begins to murder indiscriminately (using her meat pie business as a cover for how he disposes of the bodies).

"Sweeney Todd" is gleeful in its lust for revenge, and mixes humor with the horror to a greatly entertaining result. (And if you can't catch a stage version, a film version starring Johnny Depp and directed by Tim Burton was released a few years ago.)

"Marry Me a Little" from "Company"


Stephen Sondheim's "Company" was one of the first concept musicals, turning musical theater away from light-hearted romps where the guy always gets the girl. From this point on, musicals would begin to deal with more "real," adult themes.

In it, Bobby is turning 35 and reflecting on the lives of his married friends, seeing both the good and the bad. He is an observer, almost untouchable emotionally, and part of his charm to his friends is how he reflects what they want to see (the women see him as a sweetheart, the perfect partner, while the men envy him his bachelor life).

Eventually, though, Bobby realizes that even with all the negatives of marriage, you're not fully alive if you're alone and closed off--and he takes the first step toward connecting with another person.

Filled with memorable songs, "Company" isn't driven by a linear storyline, but more by a series of vignettes tied together by Bobby himself. If you're married, have ever been married, or are older and single, "Company" will likely resonate with you.

What is your favorite Sondheim musical?

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"Hello Little Girl" from "Into the Woods"

Into the Woods

"Into the Woods" is a favorite of high schools and community colleges; the fairy tale framework appeals to a wide audience and even those who aren't fans of musicals can enjoy its jokes and storyline. To see it as a mere fairy tale, though, is not to understand it--"Into the Woods" is actually a meditation on wishing, wanting, and the fact that getting what you want isn't always what's best for you in the end.

"Into the Woods" combines several classic fairy tales--Cinderella, Rapunzel, Little Red Riding Hood--with one of its own, the tale of a childless baker and his wife who desperately want a baby. The characters' paths cross and diverge throughout the musical, with the first act giving everyone what they want, ending happily ever after--and the second showing that happily ever after isn't exactly achievable. No "after" can ever be perfect.

Whatever level you decide to approach if from--just for fun or as a darker, more meaningful work--"Into the Woods" is immensely enjoyable, and the 1987 recording features some of Broadway's best artists in their prime.

"Finishing the Hat" from "Sunday in the Park with George"

Sunday in the Park with George

In "Sunday in the Park with George," Stephen Sondheim took inspiration from a painting by Georges Seurat, "A Sunday Afternoon on the Island of Grande Jatte." The first act follows Georges, the painter, as he struggles to finish his masterpiece and to find a balance between his art and the woman he loves, Dot. Dot demands more than he can give her, and can't understand the great heights to which painting takes Georges. Eventually, Dot leaves Georges for Louis the Baker and travels to America.

The second act follows Georges' great-grandson with Dot, a struggling artist himself who muses on the different themes of art, creation, and family.

The musical is one of only eight to win the Pulitzer Prize for drama, and features one of Sondheim's most famous songs, "Finishing the Hat"--about the struggle of an artist toward the perfect product, getting lost in one's work, and the conflicting sense of euphoria at creation and pain at watching the world go by while you isolate yourself.

Clip from "Assassins"


"Assassins" is one of Stephen Sondheim's edgier musicals, in regard to subject matter--it features the many men and women who have tried to assassinate a U.S. president. The songs by each assassin reflect the time in which the assassin lived, and the figures Sondheim highlights include John Wilkes Booth, John Hinkley, Lynne "Squeaky" Frome, Guiseppe Zengara, and more.

The assassins' stories come together around Lee Harvey Oswald, as they encourage him to shoot Kennedy and join their infamous ranks.

While the musical takes some of the most serious, disturbing, and upsetting moments from American history, it does so with a dark humor that maintains the events' serious nature while lampooning the motivations and personalities of the assassins. It's also a great, if not entirely accurate, history lesson.

Stephen Sondheim


Enjoying the Works of Stephen Sondheim

The musicals of Stephen Sondheim are highly enjoyable, offering interesting characters, complex melodies, and intelligent lyrics. You may find yourself enjoying them even more upon multiple watches/listens!

What's your favorite Stephen Sondheim musical?

Enjoy the Works of Stephen Sondheim


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    • Elizabeth Bowers profile image

      Elizabeth Wilson 

      6 years ago from Tennessee

      I adored Into the Woods. :)


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