Top 10 Ultimate Stephen Sondheim Musicals
#10: “A Funny Thing Happened on the Way to the Forum” (1962)
This musical is a bonafide classic, and the leading role of Pseudolus is one of the most acclaimed roles in Broadway history. The story follows an ancient Roman slave who helps his master win over a girl in exchange for his freedom. Many notable actors have portrayed the character throughout the years, and every actor to have played him on Broadway (Zero Mostel, Phil Silvers, and Nathan Lane) has won a Tony Award for Best Leading Actor. In fact, the original 1962 production took home six Tony awards, including the coveted Best Musical. Unfortunately, Stephen Sondheim’s composing and lyrical work for it was not, and has never been, recognized.
#9: “Pacific Overtures” (1976)
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Speaking of “unrecognized” work, “Pacific Overtures” is one of Stephen Sondheim’s underappreciated musicals, largely because it is rarely performed! This is due to the style (and exorbitant production costs) of the musical. It requires the involvement of numerous male Asian actors, and they must perform both the male and female roles, with the play staged in the traditional Japanese Kabuki style. Then there’s the 27-piece orchestra, which even Broadway can no longer do. The original show was critically praised and nominated for ten Tony awards, but it ultimately only ran for 193 performances. Sometimes a work of grand ambition can be too much for the medium.
#8: “Assassins” (1990)
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Stephen Sondheim feared that “Assassins” would be too bleak and controversial, especially as a follow-up to his family friendly “Into the Woods.” The former follows various historical characters who have attempted to assassinate, or who have successfully assassinated, American presidents, including John Wilkes Booth, John Hinckley, Jr., and Lee Harvey Oswald. Most notably, he attempts to humanize them, as it explores their character, their motivations, and the provocations of American political culture. Luckily, despite its controversial subject and approach, the play was an enormous success, and it contains a unique soundtrack that mixes a wide range of genres from throughout history. The multiple Tony award winner is one of Sondheim’s most daring and uncompromising works, and undeniably among his most memorable.
#7: “Gypsy” (1959)
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“Gypsy” is one of the most renowned musicals in American history. It follows Rose, a harsh and overbearing stage mother who forces her daughters into show business. It’s based on the life and memoirs of Gypsy Rose Lee, a burlesque entertainer from the early 20th century who became famous for her provocative striptease. It originally ran on Broadway from 1959 to 1961 and has been revived four times, winning a combined total of six Tony awards. The character of Rose has since become iconic, and the work features a timeless soundtrack that includes the classic Rose’s Turn, which is often regarded as one of the most show-stopping 11 o’clock numbers in Broadway history.
#6: “Company” (1970)
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“Company” is yet another example of how Stephen Sondheim enjoys pushing buttons and breaking boundaries. “Company” follows a man named Robert, whose 35th birthday celebration brings together his three girlfriends and numerous married friends. Sondheim wanted to address the issues and problems of Broadway attendees of the time – that is, the rich and the upper middle class. According to Sondheim, these people went to the theatre to escape their troubles, but he wanted to present the audience with the realities of their lifestyles. Luckily, they weren’t too offended. In fact, “Company” was praised for its realism and adult themes. It was nominated for a then-record fourteen Tony awards, winning six, including Best Musical and both Best Score and Best Lyrics for Sondheim.
#5: “A Little Night Music” (1973)
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“A Little Night Music” is one of Sondheim’s most complex works. It is famous for being particularly challenging for both the performers and musicians, as the singing contains many high notes, and the score employs difficult time signatures and intricate arrangements. But while it may be a pain for performers, it is a delight for audiences. The musical contains one of Sondheim’s greatest and most melancholic scores, a Tony-winning tour de force that encompasses the many aspects and faces of love. Topping it off is the classic showstopper Send In the Clowns, which has since become one of Sondheim’s most popular songs - having Frank Sinatra covering it by probably helped a bit!
#4: “Sunday in the Park with George” (1984)
“Sunday in the Park with George” came at a hard time in Sondheim’s life. His previous work, “Merrily We Roll Along,” had just bombed, and he was left contemplating his future in theatre. His frequent collaborator James Lapine convinced him to carry on, and the two were soon inspired by the painting A Sunday Afternoon on the Island of La Grande Jatte. They then wrote a musical about its painter, Georges Seurat, and the creative process involved in producing the work. What resulted was an utterly magnificent play that has won numerous accolades, including two Tonys, seven Laurence Olivier Awards, and even the Pulitzer Prize for Drama. Much like the painting that inspired it, this musical is a masterpiece.
#3: “West Side Story” (1957)
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We don’t think it’s hyperbole to call “West Side Story” one of the most important works in theatre history. The first Broadway production, which also happened to be Sondheim’s Broadway debut, opened at the Winter Garden in September 1957 and ran for whopping 732 performances. It was also nominated for six Tony awards, winning for Choreography and Scenic Design. A very successful West End production followed, as did a movie that won an astounding ten Academy Awards. It was a groundbreaking theatrical performance in many ways, from its unique blending of musical genres to its Shakespearean story and topical themes surrounding social issues and racism. Even early in his career, Sondheim and his lyrics were taking risks and changing the landscape and course of Broadway.
#2: “Into the Woods” (1986)
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“Into the Woods” is another stellar entry in the Sondheim-Lapine pantheon. It tells an exceptional and magical story involving the intertwining of numerous Charles Perrault and Brothers Grimm stories and their classic fairy tale characters. And, like most of Sondheim musicals, it contains mature themes, including the blurry nature of morality, the costs of wish fulfillment, and the consequential nature of parent-child relationships. True to fairy tales, it mixes childish wonder and magic with important life lessons and heady themes, all brought to life with a delightful Tony-award winning score by Sondheim. It has since become one of his most popular and most performed works, for good reason. Before we look at Sondheim’s greatest accomplishment, here are a few honorable mentions. “Follies” (1971) “Merrily We Roll Along” (1981) “Passion” (1994) “The Frogs” (1974) “Anyone Can Whistle” (1964)
#1: “Sweeney Todd: The Demon Barber of Fleet Street” (1979)
“Sweeney Todd” is not an original work, as it’s based off a 1973 play by Christopher Bond, which in turn was inspired by the character found in the penny dreadfuls of Victorian England. But despite this, it was Sondheim’s music and lyrics that elevated the story of Sweeney Todd into pop culture consciousness. He also gave Sweeney a complexity and humanity that he had been missing for over a century, while still retaining the visceral horror of the story. The result was a macabre work whose original Broadway production won eight Tonys and whose original London production nabbed two Olivier awards. It has since been revived and adapted on numerous occasions. It’s one of the most affecting musicals of all time, and arguably unlike anything else you’ll see on the stage.
