Stephen Sondheim‘s name is synonymous with musical theatre. If you’ve any interest at all in musicals, you more than likely have seen a few of his plays, whether at the theatre or on the silver screen. Numerous film adaptations have been made of Sondheim’s work, and some of these films have became classics in their right. This month’s Retrospective Roundtable looks at a handful of Sondheim’s adaptations and projects, celebrating the work of a genius.

Gypsy (1962)

By Alex Sitaras

One of Stephen Sondheim’s first musicals, Gypsy revolves around the life of a troubled matriarch, Rose (Rosalind Russell), who seeks to live vicariously through her children. Pushing them to achieve success on the theatrical stage, she is admirable in her dedication and steadfast determination to ensure her children’s success. However, she pushes and pulls too hard, and those close to her drift away as her obsession distances her from those who love her. Rose’s – I hate to say it – favorite daughter leaves the act and, by extension, thrusts her sister into the limelight as Rose insists on making Louise (Natalie Wood) a star nonetheless.

Stephen Sondheim’s involvement in Gypsy was limited to lyrics; however, ‘limited’ might be a poor choice of words. Lyrics, especially when Mama Rose sings them, are at the forefront of exploring characters’ relationships with each other. They help bring us closer to Rose and allow us to sympathize with her, while also maintaining the perspective that it isn’t best for one to live through their children. The lyrics build to a reconciliation scene between Rose and Louise that has been interpreted and reinterpreted through various adaptations and Broadway revivals, and grants the musical its staying power over the decades.

A Funny Thing Happened on the Way to the Forum (1966)

By Henry Baime

Though it may not remain as popular today as some of his other works, A Funny Thing Happened on the Way to the Forum, the first musical for which Stephen Sondheim wrote both the lyrics and music, is always the first of his works to jump to my mind in any discussion about America’s greatest musical theatre mind. I first saw the film adaptation, which followed four years after the stage version’s Broadway debut, in the seventh grade when I began taking Latin classes and I revisited it numerous times in the years following.

Directed by Richard Lester, hot off the success of Help! and A Hard Day’s Night, A Funny Thing Happened on the Way to the Forum is a hilarious ride through the villas of Ancient Rome that also serves as one of the greatest musical adaptations. Despite ditching some of Sondheim’s work from the stage version, it still keeps the backbone of it and makes something entirely new for the screen, integrating songs and plot lines into set pieces that are only possible on film, rather than merely replicating stage sets and serving as a poor mirror of source material. By creative cast choices such as Buster Keaton (still doing his own stunts in his final film role) alongside Zero Mostel and other original stage cast members, it proved a wonderful marriage of Sondheim’s work to the screen that allowed his artistry to shine through without stifling that of the film’s cast and crew.

The Last of Sheila (1973)

By Eugene Kang

Stephen Sondheim was most famously a preeminent Broadway composer and lyricist, but he was also a true Renaissance man. He competed on The $64,000 Question, pioneered the modern American crossword puzzle, and wrote for both TV and film, most notably, the script for The Last of Sheila, which he co-authored with Anthony Perkins of Psycho fame.

Sondheim was known for his love of parlor games and would often host real-life mystery parties where his guests would have to solve clues that he had embedded everywhere. Indeed, The Last of Sheila actually starts out this way, with movie producer Clinton Greene (James Coburn) proposing a game during a trip he is hosting where each of the contestants has a secret, and they all must discover what everyone else’s secret is while protecting their own. The game soon takes a dark turn as the secrets turn out to be a bit too close to the truth for a mere parlor game.

While murder and deception abound, The Last of Sheila is luxury porn to some extent. The movie takes place on a yacht trip and beautiful seaside locations feature prominently. In fact, Rian Johnson cited The Last of Sheila as one of the inspirations for his mystery film Knives Out, which luxuriates in the privileged lives of the suspects. There is also enough clever dialogue and precise characterization that makes this movie come alive as kind of a real-life Clue with high stakes. Sondheim clearly brought his own sharp eye to characterization that could be found in his musicals while also going really far with the main conceit.

Into the Woods (2014)

By Alex Sitaras

Following the success of Sunday in the Park with George, Sondheim collaborated again with James Lapine on Into the Woods, Sondheim writing the music and lyrics, Lapine the book. The musical went on to even greater success than its predecessor, won three Tony awards, and was adapted to film with an excellent cast including Meryl Streep, Emily Blunt, Anna Kendrick, and Chris Pine.

Into the Woods meshes together Brothers Grimm fairy tales, the stories of Cinderella, Little Red Riding Hood, Rapunzel, and Jack and the Beanstalk, to create a brand new fairytale that centers on the circumstances that occur as these characters meet in the woods. The green, forested unknown is most certainly its own character, and is provided with both the titular and opening number of the musical. Like most fairy tales, circumstance plays a pivotal role in Into the Woods, as does uncertainty, and what first seems as happily ever after is shortly dismantled as characters confront both fear and inhibition. Central to Into the Woods is the theme of parenthood, the play drawing on Sondheim’s experiences as a child and his relationship with his parents.

West Side Story (2021)

By Eugene Kang

West Side Story on Broadway was Stephen Sondheim’s breakout artistic work, yet as a lyricist, his contribution often gets overshadowed by Leonard Bernstein’s transcendent music and Jerome Robbins’ choreography. While the original 1961 film adaptation is still popular and very influential, it hasn’t aged well in certain respects. For a film featuring Puerto Rican actors, West Side Story featured very few performers of actual Latin heritage. Natalie Wood was of Russian descent and George Chakiris who plays Bernardo in brownface was of Greek descent. Even Rita Moreno was forced to put on brown makeup to make her look more stereotypically Latina. Also, Chakiris and Moreno act and perform circles around both Richard Beymer and Natalie Wood, the supposed leads of the story. 

Stephen Spielberg manages to make a loving homage to the original film while infusing it with new life. Spielberg knows how to move his camera to enhance choreography. He also makes this West Side Story less stage-bound and uses large environments to stage many of his dance numbers. Also, Tony Kushner’s screenplay gives depth to all the characters, even someone as inconsequential in the previous movie as Chino, Maria’s main suitor besides Tony. While Sondheim was bound by moral conventions with his lyrics (“mother-lovin’ streets), there is still an edge to his words that hasn’t gone away. The most notable example of this may be ‘Officer Krupke’, where the Jets reenact how every institution of society has failed them. It is the Jets songs that has aged the best, mostly because the problems it talks about have unfortunately not gone away. Even though the song is meant to sung with a comic delivery, the actors and Spielberg’s dynamic staging within a courthouse that gets increasingly devastated by the Jets’ dancing make this a more trenchant affair, underlining the edge that this song always had.