When the news broke on Friday, November 26, that the legendary Broadway composer and lyricist Stephen Sondheim had died aged 91, the world’s theatrical community went into mourning. That evening, fans lined up outside Marie’s Crisis Café, a piano bar in Greenwich Village, to sing and grieve together. On Sunday, crowds gathered for a tribute performance in Times Square, and in London’s West End, theatre lights were dimmed.

Sondheim was born into a Jewish family in New York City in 1930. His father was a manufacturer of dresses designed by his mother. In a childhood cushioned by wealth, he was often lonely. When his parents divorced, his father sued unsuccessfully for child custody, and Sondheim would later describe his mother as emotionally abusive. He grew close to Oscar Hammerstein II, father of his schoolmate James, and a playwright whom, in partnership with composer Richard Rodgers, wrote some of Broadway’s most memorable musicals, including Oklahoma!, Carousel, South Pacific, The King and I, and The Sound of Music. Hammerstein became both a father figure, and musical mentor to the young Stephen.

After a few years of struggle, Sondheim was recommended to composer Leonard Bernstein, and became his lyricist for West Side Story (1957.) “Lenny suffered from something Madonna, when I worked with her, called ‘important-itis’,” he told The Guardian in 2010. He went on to write lyrics for Gypsy (1959), based on the life of burlesque star Gypsy Rose Lee. In 1962, his first production as both composer and lyricist – A Funny Thing Happened On the Way to the Forum – opened on Broadway, running for 984 performances.

Following another fallow period, Sondheim’s next great success, Company (1970), began an extraordinary run of shows which redefined musical theatre, including Follies (1971), A Little Night Music (1973), Sweeney Todd (1979), and Into the Woods (1987.) From an early age, he was strongly influenced by cinema. He preferred classic Hollywood dramas such as Citizen Kane to the lightweight format of most movie musicals, and is credited with bringing adult themes and intellectual heft to musical theatre.

In 1973, his first screenplay, The Last of Sheila, co-written with Anthony Perkins, was produced. This stylish neo-noir mystery attracted an all-star cast, and is said to have inspired the 2019 thriller, Knives Out. Continuing his cinematic ventures, he wrote ‘Goodbye for Now,’ the theme song for Warren Beauty’s epic historical drama, Reds (1981.) They were reunited in 1989 for a very different film project – a live-action adaptation of Dick Tracy, the syndicated newspaper comic strip about a tough, principled detective which made its debut in 1931, and continues to this day.

Pop superstar Madonna was cast as Beatty’s foil, Breathless Mahoney, a brassy nightclub singer who vies with Tess Trueheart (Glenne Headly) for his affections. The supporting cast included Al Pacino as mobster Big Boy Caprice, and Mandy Patinkin, who had starred in Sondheim’s 1984 show, Sunday in the Park With George. “Not only was it for a movie based on a cartoon I had grown up with, it was set in the 1930s and thus invited pastiche, something I loved writing,” Sondheim recalled in his 2011 book, Look, I Made a Hat. “Better yet, the songs were to decorate the plot rather than enhance it, which made them easy to write, and when Warren hired Madonna, no less, to play Breathless, I thought it might even be my chance to have a hit record.”

Madonna recorded three Sondheim titles: ‘Sooner or Later (I Always Get My Man)’, ‘More,’ and ‘What Can You Lose,’ a duet with Patinkin. Sondheim also wrote two other songs, ‘Back in Business’ (a group performance), and ‘Live Alone and Like It,’ sung by Mel Tormé.

Performing Sondheim’s music was challenging for Madonna, a largely self-taught pop singer with limited experience in musical theatre. According to Rikky Rooksby, author of Madonna: The Complete Guide to Her Music (2004), Sondheim initially doubted her abilities, but was said to be pleased with the result. “He writes in a kind of chromatic wildness,” Madonna said at the time. “For instance, one song was written in five sharps. Another was a torch song, kind of slow and sad, that a singer sings in a smoky nightclub at three in the morning when the club is empty, kind of melancholy, just a piano and a voice.”

In addition to Dick Tracy’s official soundtrack, Madonna released a full album, I’m Breathless, featuring songs from and inspired by the movie – some co-written with producer Patrick Leonard – plus the dance anthem ‘Vogue.’ “I want people to think of me as a musical comedy actress,” she explained. “That’s what this album is about for me. It’s a stretch. Not just pop music, but songs that have a different feel to them, a theatrical feel.” One of her standout numbers, ‘Back in Business,’ is unrelated to Sondheim’s song of the same name. Although no match for the likes of Batman or Superman at the box office, Dick Tracy was well-received, and Madonna’s gamble paid off.

Celebrity author Randy J. Taraborrelli wrote that she tackled Sondheim’s selections “like a Broadway veteran,” adding, “One might wonder what a singer like Barbara Streisand would have brought to the production that Madonna didn’t, but such musing doesn’t detract from the fact that Madonna’s performance truly is sublime” (from Madonna: An Intimate Biography, 2001.)

British author Lucy O’Brien was less convinced, however, preferring Madonna’s own material – particularly ‘Something to Remember,’ which she would reuse as the title for a 1995 compilation – to the other tracks, “most of which have a stagey air. That studied approach is most in evidence on the three Stephen Sondheim songs,” O’Brien argued, in Madonna: Like an Icon (2007). “She tries hard, pitching her voice deep and carefully holding and bending notes where required. She pulls it off – but like an actress, playing a part … She had yet to do the vocal training that so transformed her voice after Evita.”

“Sondheim’s entries put Madonna through her paces as a singer, and she sizzles on all of them,” Quentin B. Harrison reflected in Song Redux: Madonna (2018.) “That none of the Sondheim songs got the single treatment … was a missed opportunity.” In a posthumous tribute to Sondheim on her Culled Culture blog, Genna Rivieccio has noted that Madonna co-produced all three of his songs (although she didn’t get a writing credit.) “With ‘More’ acting as something like a sequel to ‘Material Girl’ … Madonna was already well-versed in how to convey her lust for cold, hard cash,” Rivieccio noted. “Luckily, Madonna has always known how to merge art and commerce … As such, she still knows how to convey emotion when the moment calls for it—as it does on ‘What Can You Lose.’”

However, it was ‘Sooner or Later’ that won Sondheim – and by proxy, Madonna – an Oscar nomination. Competing against Jon Bon Jovi’s ‘Blaze of Glory’ and Harry Connick Jr.’s ‘Promise Me You’ll Remember’ (from The Godfather Part III), ‘Sooner or Later’ was performed by Madonna herself at the 1991 ceremony. “I felt awful for her when I watched her hands trembling [on the live telecast],” Christopher Ciccone recalled in his 2008 memoir, Life With My Sister Madonna. “There were no screaming fans, and she – who always hated not moving while she performed – had to stand still while she sang. Had she been singing to an audience of fans, she wouldn’t have been at all nervous. But this time she was performing in an auditorium full of established actors and actresses, a group of people to which she didn’t really belong, who didn’t respect her as an actress but whose respect she desperately wanted to win.”

Nonetheless, Madonna’s delivery was pitch-perfect, and later that night, ‘Sooner or Later’ was named Best Original Song. Sondheim didn’t attend the ceremony, and dancer turned actor Gregory Hines collected the award on his behalf. “Madonna was right there in the front row,” Matthew Rettenmund noted in his Encyclopedia Madonnica 20 (2015), joking that perhaps Sondheim “realised he would never receive his Oscar if Madonna got her mitts on it.”

While Madonna has not revisited the I’m Breathless tracks (except ‘Vogue’) since the 1990 Blond Ambition tour, she would tackle another Sondheim standard, ‘Send in the Clowns’ (from A Little Night Music) during her ‘Tears of a Clown’ cabaret, first performed at a free show in Melbourne, Australia during the final leg of her Rebel Heart tour in 2016, and reprised a few months later at a fundraiser for her Raising Malawi foundation at Art Basel Miami.

Just months after the release of Dick Tracy in 1990, Sondheim’s latest show, Assassins, opened on Broadway, with Passion following in 1994. Neither were hugely popular, although the latter has the distinction of being the shortest-running production to win a Tony award. Although revered by many, Sondheim suffered his share of hits and misses, and even considered leaving the theatre after the failure of Merrily We Roll Along (1981.) His final effort, Bounce (2003), failed to reach Broadway; but he remained active on the stage, screen, and as a writer, until shortly before his death. “There’s not going to be another Steve Sondheim,” Mandy Patinkin told the Financial Times. “There’s just one Shakespeare and one Sondheim and we’re lucky that we have them forever. The fact that I got to work and be a friend and be in the room with one of those guys? I can’t get over it.”