Musical master of Broadway

Renowned for his wit and wordplay, Stephen Sondheim redefined the American musical

Stephen Sondheim, the composer-lyricist who transformed the American musical, died last Friday, aged 91.

Sondheim, whose eight lifetime Tony Awards surpassed the total of any other composer, was renowned for his wit and wordplay as well as his complex, versatile compositions, which were often incredibly difficult to sing.

Here are seven of his best musicals.


Sondheim made his Broadway debut as the lyricist for this musical, which transposed Shakespeare's Romeo And Juliet to the Upper West Side of New York City, as two star-crossed teenagers are caught between rival street gangs.

Several of the songs, set to music by Leonard Bernstein, became Broadway classics, from the love duet Tonight to the rambunctious America, sung by Puerto Rican immigrants.

A 1961 film adaptation won 10 Academy Awards, the most for any musical film, while another directed by Steven Spielberg will be out next month.

2 GYPSY (1959)

Based on the memoirs of striptease artiste Gypsy Rose Lee, this musical honed the archetype of the stage mother in Rose, a domineering matron who pushes her daughters into show business but becomes ultimately estranged from them.

Sondheim wrote the lyrics to music by Jule Styne, and the songs here include the cheeky You Gotta Get A Gimmick and the showstopper Rose's Turn.

3 COMPANY (1970)

  • Tributes

    Tributes poured in for Broadway legend Stephen Sondheim, who died last Friday at the age of 91 at home in Roxbury, Connecticut.

    British composer Andrew Lloyd Webber on Twitter called him "the musical theatre giant of our times, an inspiration not just to two but to three generations", adding: "Your contribution to theatre will never be equalled."

    Influential British theatre producer Cameron Mackintosh said in a statement to The Guardian: "The theatre has lost one of its greatest geniuses and the world has lost one of its greatest and most original writers. Sadly, there is now a giant in the sky."

    Hamilton creator Lin-Manuel Miranda shared on social media an e-mail from Sondheim, his mentor, about Tick, Tick…Boom!, the Jonathan Larson musical which Miranda recently directed as a Netflix film. Sondheim, who was the late Larson's idol, is played by Bradley Whitford in the film, and his real voice appears in a voicemail recording.

    Miranda had e-mailed Sondheim to say "his ears must be burning from the countless Sondheim kindnesses being shared from the generations of writers he mentored".

    Sondheim had replied: "Thanks for the nice boost to my spirits, Lin. It's an aspect of my life I'm proud of. I feel as if I've repaid (partially, at least) what I owe Oscar," referring to his own mentor, the lyricist and playwright Oscar Hammerstein II.

    Miranda concluded in his post: "Steve: you repaid your debt to Oscar 1,000 times over. We love you. I love you."

    Hollywood stars including Hugh Jackman, Anna Kendrick and Jake Gyllenhaal also paid tribute to the late composer. Jackman wrote on Twitter: "Every so often, someone comes along that fundamentally shifts an entire art form. Stephen Sondheim was one of those."

    Former United States secretary of state Hillary Clinton posted on Twitter a photo of herself and her husband, former US president Bill Clinton, applauding Sondheim at an award ceremony. "A peerless composer and lyricist, Stephen Sondheim stirred our souls, broadened our imaginations, and reminded us that no one is alone," she wrote.

    Several, including Broadway stars Bernadette Peters and Josh Gad, compared him to playwright William Shakespeare. "Perhaps not since April 23rd of 1616 has theatre lost such a revolutionary voice," Gad wrote on Twitter, referring to the date of Shakespeare's death.

    Peters, a frequent Sondheim collaborator, told The New York Times: "He was like Shakespeare, and what a privilege to be able to say, 'Steve, what did you mean when you wrote that?' You could get it right from the horse's mouth. I always say, he gave me so much to sing about."

Company revolves around a single man, Robert, whose friends are all married or engaged couples. In a series of vignettes linked by his 35th birthday, his friends try to find him a girlfriend even as they themselves struggle with their relationships.

The musical is especially known for the song Being Alive, in which Robert realises that "alone is alone, not alive". In the Oscar-nominated divorce film Marriage Story (2019), the male protagonist, played by Adam Driver, sings the entire song in a bar.

A Broadway revival of Company was slated to open on Sondheim's 90th birthday last year, but was suspended due to the Covid-19 pandemic. It will now open next month. Sondheim attended a Nov 15 preview before his death.


Inspired by the 1955 Ingmar Bergman film Smiles Of A Summer Night, this musical about fraught romance in 1900s Sweden plays with dance-time signatures, featuring the waltz, the sarabande, the mazurka and more.

It contains one of Sondheim's loveliest songs, Send In The Clowns, a plaintive, wry lament about missed opportunities.


In this macabre masterpiece, a vengeful barber in Victorian London collaborates with his amoral landlady to turn his customers into meat pies, even as he pursues vengeance against the judge who robbed him of his wife and daughter years ago.

Amid the bloody plot and shrieking score, Sondheim's gift for wordplay sizzles through in darkly funny songs like the pun-stuffed A Little Priest, in which pie flavours include "shepherd's pie peppered with actual shepherd on top" and "actor", which "always arrives overdone".

Actor Johnny Depp played the demon barber in a 2007 Tim Burton film alongside Helena Bonham Carter.


Sondheim and his collaborator James Lapine won the 1985 Pulitzer Prize for Drama for this innovative musical about the French pointillist painter Georges Seurat and his painting, A Sunday Afternoon On The Island Of La Grande Jatte.

The songs also chart the relationship between George and his long-time mistress Dot, who models for him but grows dissatisfied with his inattention.


This dark, beguiling musical subverts Brothers Grimm fairy tales such as Cinderella, Rapunzel, Jack And The Beanstalk and Little Red Riding Hood. Disaffected princesses, impulsive children and a witch wander the woods, their stories intertwining with that of a childless baker and his wife.

A 2014 Disney film adaptation featured Meryl Streep, Emily Blunt and Anna Kendrick.

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A version of this article appeared in the print edition of The Straits Times on November 29, 2021, with the headline Musical master of Broadway. Subscribe