The Best Musicals by Stephen Sondheim

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Updated August 15, 2023 2.0K votes 388 voters
Over 300 Ranker voters have come together to rank this list of The Best Musicals by Stephen Sondheim
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Often inspired by fairy tales, folklore, and classic literature, Stephen Sondheim musicals are beloved in the theater world. Often imbued with a touch of the macabre, Sondheim's works have a penchant for bringing archetypal narratives and characters to a more modern setting. While he sometimes pens bizarre musicals and disturbing stories, Sondheim's works never cease to fascinate. While all the man's shows certainly have their charm, what are truly the best Stephen Sondheim musicals? Below, you'll find all his plays ranked by fans. 

The top Stephen Sondheim musicals are filled with memorable songs that are often emotionally direct and inspiring. Sondheim has collected multiple Tony Awards over the years including Best Musical winners for A Funny Thing Happened on the Way to the Forum (1963), A Little Night Music (1973), Sweeney Todd: The Demon Barber of Fleet Street (1979), and Passion (1994). His works have also solidified their place in more modern pop culture, with film adaptions of plays like Into the Woods captivating audiences. If you're in need of some show tunes recommendations, browse this list!  

Most divisive: Anyone Can Whistle
Ranked by
  • Sweeney Todd: The Demon Barber of Fleet Street
    1
    Sweeney Todd: The Demon Barber of Fleet Street is a 1979 musical thriller with music and lyrics by Stephen Sondheim and book by Hugh Wheeler. The musical is based on the 1973 play Sweeney Todd, the Demon Barber of Fleet Street by Christopher Bond. Set in 19th century England, the musical tells the story of Benjamin Barker, alias Sweeney Todd, who returns to London after 15 years' transportation on trumped-up charges, to take revenge on the judge who banished him. Sweeney Todd opened on Broadway in 1979 and in the West End in 1980. In addition to several revivals the musical has been presented by opera companies. It won the Tony Award for Best Musical and Olivier Award for Best New Musical.
  • Into the Woods
    2
    Into the Woods is a musical with music and lyrics by Stephen Sondheim and book by James Lapine. The musical intertwines the plots of several Brothers Grimm and Charles Perrault fairy tales, exploring the consequences of the characters' wishes and quests. The main characters are taken from "Little Red Riding Hood", "Jack and the Beanstalk", "Rapunzel", and "Cinderella", as well as several others. The musical is tied together by a story involving a childless baker and his wife and their quest to begin a family (the original beginning of The Grimm Brothers' "Rapunzel"), their interaction with a witch who has placed a curse on them, and their interaction with other storybook characters during their journey. The musical debuted in San Diego at the Old Globe Theatre in 1986 and premiered on Broadway on November 5, 1987, where it won several Tony Awards, including Best Score, Best Book, and Best Actress in a Musical (Joanna Gleason), in a year dominated by The Phantom of the Opera (1988). The musical has since been produced many times, with a 1988 US national tour, a 1990 West End production, a 1997 tenth anniversary concert, a 2002 Broadway revival, a 2010 London revival, and in 2012 as part of New York City's outdoor Shakespeare in the Park series. A Disney film adaptation directed by Rob Marshall and starring Meryl Streep, Emily Blunt, James Corden, Anna Kendrick, Chris Pine, Tracey Ullman, Christine Baranski and Johnny Depp was released in 2014. The film grossed over $213 million worldwide, and received three Academy Award nominations and three Golden Globe Award nominations.
  • Company
    3

    Company

    150 votes
    Company is a 1970 musical comedy with music and lyrics by Stephen Sondheim and book by George Furth. The original production was nominated for a record-setting fourteen Tony Awards and won six. Originally titled Threes, its plot revolves around Robert (a single man unable to commit fully to a steady relationship, let alone marriage), the five married couples who are his best friends, and his three girlfriends. Unlike most book musicals, which follow a clearly delineated plot, Company is a concept musical composed of short vignettes, presented in no particular chronological order, linked by a celebration for Robert's 35th birthday. Company was among the first musicals to deal with adult themes and relationships. As Sondheim puts it, "Broadway theater has been for many years supported by upper-middle-class people with upper-middle-class problems. These people really want to escape that world when they go to the theatre, and then here we are with Company talking about how we're going to bring it right back in their faces."
  • Sunday in the Park with George
    4
    Sunday in the Park with George is a musical with music and lyrics by Stephen Sondheim and book by James Lapine. The musical was inspired by the painting "A Sunday Afternoon on the Island of La Grande Jatte" by Georges Seurat. A complex work revolving around a fictionalized Seurat immersed in single-minded concentration while painting his masterpiece and the people in that picture, the Broadway production opened in 1984. The musical won the 1985 Pulitzer Prize for Drama, two Tony Awards for design, numerous Drama Desk Awards, the 1991 Olivier Award for Best Musical and the 2007 Olivier Award for Outstanding Musical Production. It has enjoyed several major revivals, including the 2005-06 UK production first presented at the Menier Chocolate Factory and its subsequent 2008 Broadway transfer.
  • West Side Story
    5

    West Side Story

    167 votes
    West Side Story is an American musical with a book by Arthur Laurents, music by Leonard Bernstein, libretto/lyrics by Stephen Sondheim, and conception and choreography by Jerome Robbins. It was inspired by William Shakespeare's play Romeo and Juliet. The story is set in the Upper West Side neighborhood in New York City in the mid-1950s, an ethnic, blue-collar neighborhood. The musical explores the rivalry between the Jets and the Sharks, two teenage street gangs of different ethnic backgrounds. The members of the Sharks, from Puerto Rico, are taunted by the Jets, a Caucasian gang. The young protagonist, Tony, a former member of the Jets and best friend of the gang leader, Riff, falls in love with Maria, the sister of Bernardo, the leader of the Sharks. The dark theme, sophisticated music, extended dance scenes, and focus on social problems marked a turning point in American musical theater. Bernstein's score for the musical includes "Something's Coming", "Maria", "America", "Somewhere", "Tonight", "Jet Song", "I Feel Pretty", "A Boy Like That", "One Hand, One Heart", "Gee, Officer Krupke", and "Cool".
  • Merrily We Roll Along
    6

    Merrily We Roll Along

    100 votes