5 Essential Stephen Sondheim Musicals

December 2, 2023

Stephen Sondheim, a legendary American composer and lyricist, is widely regarded as one of the foremost figures in musical theater. Known for his intricate and innovative work, Sondheim has left an indelible mark on the genre with iconic productions such as Sweeney Todd, Into the Woods, and West Side Story.

His unparalleled ability to blend complex lyrics with rich, emotive melodies has earned him numerous accolades, including multiple Tony Awards, and his influence continues to shape the landscape of musical theater.

5 Essential Stephen Sondheim Musicals

American composer Stephen Sondheim was born in New York City on March 22nd, 1930. He grew up on the Upper West Side of Manhattan until his parents divorced, then he moved to a farm in Pennsylvania. It was there, at the age of 10, that he became friends with James Hammerstein, the son of the famous lyricist and playwright Oscar Hammerstein, who took Sondheim under his wing and served as a surrogate father to him through that difficult time in his life.

Sondheim wrote some of the finest songs in musical theater history, on the same level of excellence as Andrew Lloyd Webber and Leonard Bernstein. Choosing can be challenging, but there are a few essential Sondheim Musicals every aspiring performer should see.

1. Assassins 

Sondheim provided the lyrics and music to this fascinating show, which opened on Broadway in 2004 and was based on a book by John Weidman. This humorous musical explores the minds of the men and women who attempted as well as succeeded in killing the American Presidents. The show examines the motivation behind their acts of lunacy and abstract psychology.

Assassins is presented in a revue-style with various styles of music, including the songs “The Ballad of Booth” and “Gun Song.” “The Ballad of Booth” contains the lyric, Every now and then the country goes a little wrong.” Although this sentiment may be true and their actions wrong, we are fascinated by these killers and their stories.

John Wilkes Booth, Lee Harvey Oswald, and Sara Jane Moore are included in this cast of characters, both historical and fictional. The show opens with the number Everybody’s Got the Right to Be Happy, which gives us an idea of how these men and women think. Sondheim is known for controversial shows, and he knew that this musical would likely have some backlash. Assassins is bold and brilliant and was recognized with five Tony Awards in 2004.

2. Company

This funny musical comedy centers around Bobby and his best friends, who are all married or engaged. Throughout the show, Bobby attends a series of dinners and parties with his married friends, where he tries to make sense of his bachelor ways.  He learns that his friends’ marriages are not exactly what they seem. The relationships reveal infidelities, alcoholism, and regret.

Along the way, he questions whether it’s best to be single…. or not. Company captures honest moments of vulnerability, relationships, and marriage. In a society where we often use film, social media, and theater to escape everyday problems, this show puts those problems back in your face. This modern musical features the songs Company, Marry Me a Little, Side by Side, and The Little Things You Do Together. It debuted on Broadway in 1970, and since then, it has won seven Tony Awards and five Drama Desk Awards.

3. Sweeney Todd: The Demon Barber of Fleet Street 

The legend of Sweeney Todd was already a story before it became a musical. Dark and humorous, this musical follows the story of Benjamin Barker, who arrives home in London after serving a 15-year prison sentence given to him by a corrupt judge who tore his life and family apart. The feeling of revenge overcomes him. Benjamin creates a new alias, Sweeney Todd, to continue working in his barber shop above Mrs. Lovett’s foul-smelling and struggling pie shop.

Mrs. Lovett recognizes him immediately as Benjamin Barker and tells him that the judge sexually assaulted his wife and now has his daughter Johanna. The two of them join forces and form a plan to use the bodies of Sweeney’s murdered victims as meat for the pies, which they will sell to unsuspecting customers.  While waiting for the judge to visit the shop, we are introduced to other interesting characters in London. This dark comedic tail ends with a twist and the song Ballad of Sweeney Todd.

4. Into the Woods 

This 1987 Sondheim musical is a woven web of Brothers Grimm stories and fairy tales. The narrator introduces us to a baker and his wife who wish to start a family but have unfortunately been cursed by a Witch. In order to remove the curse, they go off into the woods and must return with four potion ingredients requested by the Witch. Through this story, we are introduced to the other fairy tale characters, including Cinderella, Jack, Little Red Riding Hood, the Wolf, the Prince, and Rapunzel, all of whom have wishes.

Each of their tales intertwines in the woods, and they all discover the consequences that occur as they try to fulfill their wishes. This show is a brilliant mix of desire, deceit, and deception. Into The Woods has many amazing solo songs, but the song that truly stands out is “Children Will Listen,” which is sung by the Witch.  It perfectly sums up the feel and message of the show.

stephen sondheim musicals
Into the Woods, as performed at NYFA’s musical theatre school.

It also includes the songs “I Know Things Now,” “Giants in the Sky,” and “Stay with Me.” This show continues to be a success, as it was recently made into a film in 2014. I think the Prince’s line “Anything can happen in the woods” is a perfect way to describe this adventurous show.

5. West Side Story 

Stephen Sondheim played a crucial role in creating West Side Story, a groundbreaking musical that reimagined Shakespeare’s “Romeo and Juliet” in the context of 1950s New York City. Sondheim, at the time a young lyricist, collaborated with composer Leonard Bernstein to create the unforgettable lyrics for the production.

His insightful and poetic lyrics in songs like “Maria” and “Tonight” contributed significantly to the musical’s emotional depth and enduring impact, solidifying Sondheim’s early reputation as a master lyricist in the world of musical theater. The show also inspired two movie musicals, including a 1961 version starring musical icon Rita Moreno, as well as a 2021 version with an all-star cast directed by NYFA Guest Speaker Stephen Spielberg.

The film also featured actress, singer, dancer, and NYFA Musical Theatre alum Ilda Mason.

Build Musical Theatre Skills at NYFA

NYFA’s musical theatre school gives students the opportunity to audition for full-fledged musicals. Studying under instructors who have toured various Broadway and touring productions, regional theaters, operas, movie musicals, and television shows, NYFA offers students real-world training that prepares them to offer their best possible performance.

Start your own movie musical adventure today with the New York Film Academy’s Musical Theatre School in New York City.