Stephen Sondheim was known for his furtive nature and as Daniel Okrent reveals in ‘Art Isn’t Easy’ the composer would deliberately dress down, even shabbily, to keep people at a distance. But however elusive Sondheim wanted to remain, he was
in the Broadway spotlight his whole life and the subject of bios, documentaries, interviews, and online lore, and adding to his dodgy mystique there’s his own two-volume 900 page quasi-memoir of all of his musicals.
‘Art Isn’t Easy’ is Okrent’s breezy fine-line portrait of Sondheim’s furtive public persona, and his chaotic private life. He was prone to mood swings, but with an iron will to do things his way, which could make lead to his biggest successes or flail in a creative hell of his own making. Often writing last minute numbers for show openings, most famously, composing ‘Send in the Clowns’ just hours before the premiere of ‘A Little Night Music.’
Okrent had access to Sondheim private writings and archival materials. He deconstructs Sondheim’s creative rigor, and essays pointed analysis of his successes and failures, onstage and backstage. The risks in the commercial theater was a high wire act of producing profitable musical theater. Sondheim’s personal life often proved just as perplexing for Sondheim to navigate. Sondheim had complicated relationships, struggled with his sexuality and the feeling that he would never fall in love.
Sondheim had a tough time his mother Foxy, who was always emotionally distant and domineering mother. When his parents divorced, mother and son moved to Doylestown, right next door to legendary Broadway composer Oscar Hammerstein. Sondheim was already composing musicals as a teen, and Oscar became his fatherly mentor, giving him honest, and often critical advice, about his dreams of being a composer-lyricist.
Okrent details Sondheim’s rocky relationships with show collaborators, the most famous being with composer Leonard Bernstein, writer Arthur Laurents and directors Harold Prince and James Lapine. And he could be openly hostile to his critics.
He drank and smoked pot as needed, never seemingly losing his professional wits. His temper, though was not so easily controlled. Sondheim was often resistant to collaborations with librettists for his musicals, or anyone who tampered with his lyrics, he fought with longtime colleagues, cut them off, but just as often went out of his way to make up…and sometimes not.
There is scant mention of such Broadway stars from his shows, including heavyweights – Patti Lupone, Bernadette Peters, and Elaine Stritch, who delivered his musical portrait of his mother, blowing the roof off belting out ‘The Ladies Who Lunch.’
As his Broadway star kept rising throughout the 60s, Sondheim was dating women, including Mary Rodgers, the daughter of lyricist Richard Rogers. Even though it was a was a lovingly platonic relationship, they seriously considered marrying. In another mutually loving relationship he courted actress Lee Remick.
Of course, in the deeply homophobic pre-Stonewall era, Sondheim was also dating men, with all the codes of silence in their homophobic place. Though he was open enough to discuss his gay (closeted) life with his psychiatrist well into middle age.
There was always gay subtext in Sondheim shows, starting with Bobby, the main character, 1970’s Company, many fans wondering whether the main character Bobby was gay coded. And just weeks before his death Sondheim approved the script changes and lived to see the previews of the gender switching hit revival of Company, with one of the original story lines about an straight couple’s wedding turned into a gay male couple’s story.
Some fans thought ‘ Into the Woods’ was a symbolic response to the AIDS crisis. Sondheim quipped “The trouble with fables … is that everybody looks for symbolism.’ As Okrent notes “Declarations about the issues of the day were simply alien to the publicly diffident Sondheim.”
In the 80s at the height of the AIDS epidemic, playwright and AIDS activist Larry Kramer approached Sondheim about writing a musical creating a show about gay men, their lives and community. Sondheim passed on the offer, his dodgy (and unconvincing) explanation being that he never writes “from an idea…or a particular subject.”
Meanwhile, his adversarial relationship with his mother was lifelong. She rarely spent time with him, but might show up for his opening nights. However starchy the relationship, Sondheim continued to take care of her financially.
Over the years Sondheim confided to his psychiatrist that he never thought he would fall in love. But in 1991 he did with a young songwriter, but it didn’t last. But late in life, in his mid-70s, he fell in love with actor Jeff Romley, who was 23. and they married in 2017, so finally came fully out, even if he didn’t want to talk about it.
Just days before his death in 2021, Sondheim was able to attend previews of the gender-switching version of Company on Broadway. His final musical Here We Are, premiered in 2023 in New York and 2025 in London and there have been a slate of revivals of his shows on Broadway, London’s West End, including his previously disastrous musical ‘Merrily We Roll Along’ also a new production of ‘Sweeney Todd’ starring Josh Groban and the 2024 production of ‘Gypsy’ starring Audra McDonald. A star-studded revue ‘Old Friends’ veteran stars covering his showstopping numbers leaving them begging for more. Cue music!
