The Top Ten Stephen Sondheim Musicals

Beau Salant ‘18 / Emertainment Monthly Staff Writer
Today, Stephen Sondheim celebrates his 85th birthday, and in acknowledgement of this monumental event in this legend’s life, Emertainment Monthly is looking back at his top 10 contributions to musical theater.

10. West Side Story

West Side Story is a fan-favorite for theater aficionados and general theatergoers alike. A modern, more cultural retelling of Shakespeare’s Romeo and Juliet, it was Sondheim’s first major success and was the first show to highlight his innate ability to write sophisticated lyrics that are catchy, advance the story and cleverly rhyme. However, like the play it is based on, West Side Story is one of this genius’ most flawed works. No matter how compelling and beautiful the score may be, the overly melodramatic story and often grandiose staging has a tendency to remove the audience from the show. This is no fault of Sondheim’s, though, as his work here still shines.
Best Lyric: The show’s most famous line, “Tonight, tonight, it all began tonight!” symbolizes not just the beginning of the epic story, but of Sondheim’s epic career, which was launched by the success of this musical.

9. Merrily We Roll Along

Although it was not a major success in its first incarnation – it was actually a major failure, playing only 16 performances on Broadway and losing a massive amount of money – many critics pointed out the rich beauty in Sondheim’s score in their otherwise negative reviews. These critics were quick to recognize the problematic book and incoherent staging, but Sondheim was the target of none of these jabs. Telling the story of a once-great composer who abandoned his entire stage career to produce films, Sondheim’s music is intricately used not only to advance the plot but also to provide the transitions between scenes, as the titular song is repeated numerous times throughout the show, to show how swiftly and quickly life rolls along.
Best Lyric: “But I just go on thinking and sweating. And cursing and crying. And turning and reaching. And waking and dying.” One of the many examples of Sondheim’s lyrics showing his true understanding of human emotion, pain and existence.

8. Sunday in the Park with George

Sondheim’s low-key, intimate musical about art, creativity and love is a moving mosaic of epic passions packed into a small and personal show. It tells the story of a reclusive painter in the process of painting his masterpiece, whose lover (and the subject of his painting) slowly teaches him to enjoy the beauty surrounding him in the world rather than focusing solely on the beauty of his work. Featuring many ballads and few showstoppers, the score is a challenging one to sing due to its intricacies in character and voice. But what the score does so well is portray the clashes in personality of its leading man and lady. The naivety of leading man George and the free-spiritedness of leading lady Dot often find themselves at odds as George sings to himself while Dot sings out to the world. Sunday in the Park with George achieves greatness when these characters balance each other, something Sondheim’s music so brilliantly achieves.
Best Lyric: In the show’s most famous number, “Move On,” Dot sings to George: “I chose and my world was shaken, so what? The choice may have been mistaken, the choosing was not.” With just these few lines, she effectively and beautifully teaches George that a life of open-minded, free-spiritedness defeats a life of naivety every time.

7. Assassins

It was a terrible idea for a musical – a show about a bunch of people who tried (some succeeding) to assassinate Presidents of the United States – but it wasn’t the first time Sondheim took on a strange topic, and it wasn’t the first time he made a strange topic work. This show perfectly shows Sondheim’s flair for dramatics, as well as his cleverness, with the idea to create the musical in the style of a carnival game, a very murderous carnival game. It’s one of his most unique and creative works to date, and it doesn’t get nearly as much attention as it should.
Best Lyric: There’s really nothing special about the word choice, but the use of the phrase “shoot a president” throughout the musical (specifically the opening number) is both eerily bone chilling and strangely hilarious, emphasizing Sondheim’s ability to evoke so many different feelings out of one repeated phrase.

6. A Little Night Music

One of the first musicals that Sondheim wrote both the music and lyrics himself for, A Little Night Music opened on Broadway with low expectations for the young Sondheim, but ended up blowing everybody away. It’s a traditional musical by Sondheim standards, but it proves that traditional can still be wonderful. The story is both emotionally harrowing and laugh out loud hilarious, as an unsatisfied, aging actress must decide which of her flings she wants to settle down with. It’s a moving story about romance and love, two of Sondheim’s favorite topics.
Best Lyric: Four words. “Send in the clowns.” It may not make much sense out of context, but when it comes up in the show, it seems to almost perfectly sum up the plot and have you feeling all sorts of emotions.

5. Passion

An army general is in love with a woman, but can’t be with her because of her terminal illness. Sondheim’s saddest musical is also one of the saddest musicals, period. One of his late-career entries, Passion is usually, undeservedly, met with mixed reactions from theatre fans and critics. Many go into the story expecting the gloriously strange shows that Sondheim became known for, like Assassins and Sweeney Todd, but instead get a very human story about lost love, grief and death. The character of Fosca alone is one of Sondheim’s best creations: a complex portrait of a woman who wants to experience love just once before her imminent death. It doesn’t get more tragic than that.
Best Lyric: “Loving you is not a choice, it’s who I am.” Have you ever loved somebody so much, but hated yourself for it? Because they mistreat you, don’t love you back, take you for granted, any reason? Then this lyric most likely speaks to you. Sondheim once again proves to have a genius understanding of human nature, knowing that we don’t choose to love. We just do.

4. Into the Woods

We all grew up with fairy tales teaching us that happy ever after is always around the corner. But what if it isn’t? Into the Woods dares to answer that question. Bringing together the beloved stories of Cinderella, Jack and the beanstalk, Little Red Riding Hood, Rapunzel and weaving them together around a story of a childless Baker, his wife and a witch who has put a curse on them, Into the Woods turns these fairy tales on their head, giving them tragic endings instead of happy ones, and teaches the valuable lesson that life doesn’t always work out the way you want it to, but even then, there is still light and love in the world. Sondheim’s music for the show is some of his most versatile, with a massive, ten-minute long opening number followed by a multitude of ballads, large group numbers and massive show-stoppers.
Best Lyric: “Careful the things you say, children will listen.” Essentially Sondheim’s middle finger to fairy tales, he teaches us that children are sensitive creatures who accept whatever is told to them. Thus, they must be treated with care and put on the right path early on, not lied to and misled for life.

3. Gypsy

Have you ever had a really terrible mother? Hopefully not, but if you did, Gypsy probably speaks to you on multiple levels. The show tells the epic story of Mama Rose, a failed actress who is determined to stop her children from suffering the same fate. A showcase role for an actress, Mama Rose is a dynamic beast, one of the most complex characters ever written in musical theater. It’s this show that demonstrates Sondheim’s knack for character work. Even beyond Mama Rose, the entire supporting cast (especially the character of Louise) is given thrillingly brilliant characters to work with. And with Sondheim’s trademark brilliant music, it’s a guaranteed treat for any audience member.
Best Lyric: “Everything’s coming up roses, this time for me!” In one of the most thrilling songs ever written for musical theater, Mama Rose declares that it’s her time to shine after everything she goes through. The song has become an anthem for anybody going through a hard time, determined to come out on top.

2. Sweeney Todd: The Demon Barber of Fleet Street

Like Assassins, Sweeney Todd doesn’t sound like your typical musical. A vengeance-filled barber returns to London to slit the throats of his enemies while his partner bakes their corpses into pies. But Sondheim’s incredible score carries the show’s unorthodox plot into theatrical bliss. Despite the horrific acts being committed in front of our eyes, we root for Sweeney Todd to achieve what he wants because Sondheim turns him into an unlikely hero, representing everybody who has ever been wronged in the world. It’s an unconventional story of redemption told with crime, a contradiction only Sondheim could get right.
Best Lyric: “Nothing’s gonna harm you, not while I’m around.” It’s so ironic that in a musical filled with bloodshed and murder, that a character sings with confidence to another character that nothing will harm them. It’s just one of the contradictions that makes Sweeney Todd so complex.

1. Company

Sondheim’s masterpiece brings all of his strengths together: unconventional stories, strong character work and breathtakingly brilliant music. Telling the story of a hedonistic womanizer who experiences a sequence of events in his life that make him realize how lonely he is, Company takes a massive amount of risks: an unlikeable lead character, a complex story and, most interestingly, a non-linear narrative (the story is told out of order). But the show works because it features everything that Sondheim does best, with him in peak form on all accounts.
Best Lyric: “Somebody crowd me with love. Somebody force me to care. Somebody let me come through, I’ll always be there, as frightened as you, to help us survive being alive.” These lines of lyric are the strongest Sondheim has ever written because of how they encompass human spirit, desire, emotion, struggle and lust all in one. Everybody in the world can somehow relate to this line, and that is something truly amazing.
Honorable Mentions: A Funny Thing Happened on the Way to the Forum and Follies