If Stephen Sondheim Taught Us Anything, It’s That Mentors Matter

The student of Oscar Hammerstein became the teacher of Jonathan Larson, Lin-Manuel Miranda and countless others

The composer and lyricist Stephen Sondheim in 1962. He passed away in November.

By Alex Lauer

There’s a newly resonant Easter egg near the end of the movie Tick, Tick . . . Boom! The semi-autobiographical musical, adapted from a show by Rent composer Jonathan Larson and released on Netflix in November, follows Larson as the up-and-coming composer and lyricist attempts to bring a production to Broadway. In the movie, as was the case in real life, his idol is Stephen Sondheim, who is convincingly played by Bradley Whitford.

Early in the film, Larson, played by Andrew Garfield, talks about how Sondheim’s praise inspired him to keep working on the musical for years. Near the end, in a moment of despair, the giant of musical theater once again provides Larson with that sustenance, this time in the form of a voicemail. But if you listen closely, it’s not Whitford speaking as Sondheim; it’s Sondheim himself. The end credits even confirm this subtle cameo. As director Lin-Manuel Miranda has since explained, Sondheim wasn’t satisfied when presented with the original scene and wanted to write and record a version himself to get his advice to the budding composer right. 

On November 26, two weeks after Tick, Tick … Boom! was released, Sondheim passed away at the age of 91. In the loving obituaries that followed, worthy of the most important musical theater artist of our time, who began as the lyricist of West Side Story and went on to compose the music and lyrics for such influential shows as Sweeney Todd, Into the Woods and Sunday in the Park With George, writers extolled Sondheim as a “titan,” a “singular” talent and “an artistic genius on the level of Shakespeare.” He was certainly these things, but he was not born that way. By his own admission, Sondheim was the result of a deliberate and intense mentorship at the hands of Oscar Hammerstein II, an experience he promised to pass on to the next generation, as his nitpicking of Tick, Tick … Boom! makes clear. 

“[Oscar Hammerstein] helped Stephen Sondheim to unleash his own creative soul,” Bruce Pomahac, who served as director of music at the Rodgers & Hammerstein Organization for over 20 years, tells InsideHook, “and Steve just went where no one had gone before, because that’s what fascinated him.”

Human beings, and Americans especially, love the narrative of the organic genius, especially ones like Sondheim who we feel were underappreciated in their prime. But Sondheim’s story is not one of a brilliant boy who toiled away alone in his room and became a legend, nor is it one of nepotism, where his association with Hammerstein, who along with Richard Rodgers created the Golden Age of musical theater with classics like Oklahoma!, Carousel, The King and I and The Sound of Music, gave him an unfair advantage. No, what we have here is one of the greatest examples of a thoroughly underappreciated part of life in the 21st century: mentorship. 

The Mentorship of Stephen Sondheim


The story of Oscar Hammerstein taking young Stephen Sondheim under his wing has been told many a time: Sondheim’s parents divorced, his mother bought a home near the Hammerstein farm in Doylestown, Pennsylvania, the young boy took on Oscar as a surrogate father and the family accepted him in turn. There are a few scraps of lore that are always attached, including, as Pomahac recounts, Sondheim’s insistence that if Hammerstein had been a geologist, he too would have been a geologist. That’s a nice tidbit, but not quite the truth, as children are impressionable beings whose dreams are seemingly cemented, blown up and reformed over and over again when confronted with reality. 

If Sondheim didn’t have it in him to follow in Hammerstein’s footsteps as a lyricist, he would certainly have changed course as a teenager. Yes, he caught the theater bug when Oscar took him to such momentous performances as the first out-of-town tryout for the musical Carousel around his 15th birthday; Sondheim has said that he wept so hard into Dorothy Hammerstein’s fur coat at the end of the first act that he permanently stained it.

But in the process of Hammerstein teaching him how to write a musical, he was also on the receiving end of feedback that would induce a different sort of weeping in any normal, emotionally vulnerable teenager. Later that year, he gave Hammerstein By George, his first attempt at a musical, and asked his mentor to give him feedback as if they didn’t know each other. (Inside, he hoped Rodgers and Hammerstein would want to produce it.) 

“‘In that case, I have to say it’s the worst thing that’s ever crossed my desk. It’s the worst thing I’ve ever seen. It’s the most unproducible. It makes no sense,’” Hammerstein said, as Sondheim recounted to Diane Sawyer in 1988. While Sondheim admitted that “worst” sounds cruel, he added, “He was not cruel that way, but he made it very clear that if I were going to ask for professional standards, he was going to treat me like a professional.” 

That cold bucket of water didn’t deter Sondheim. In fact, it may not have been in sharing Hammerstein’s Broadway smashes like Oklahoma! and Carousel where the young lyricist and composer got the most out of his mentorship. 

“He was around after Carousel for Rodgers and Hammerstein’s next show, Allegro, which was not a success,” Pomahac explains, noting that Sondheim was intimately involved in that production as a gofer, an errand boy who got coffee and typed scripts and whatever else needed doing. “That taught him probably more than any of the successes taught him because he saw the authors struggling to get something to work that wasn’t working, and also they were struggling under the pressure of a New York deadline.”

Crucially, Hammerstein’s own failure to create a hit out of his most experimental show ever did not bleed into his advice for Sondheim. He pushed his student to find his own voice rather than emulate him or anyone else. As Pomahac illustrates, “Whereas Oscar Hammerstein was sentimental, Stephen Sondheim was ironic. When Oscar Hammerstein wrote ‘I love you,’ it meant ‘I love you.’ When Stephen Sondheim wrote ‘I love you,’ it could mean ‘I hate you.’” There are certain rules when it comes to constructing a top-notch musical — as Sondheim writes in his book Look, I Made a Hat, some of Oscar’s rules were “imprinted in my DNA” — but when it came to finding one’s own style, Hammerstein recommended killing your idols, even if that meant himself. 

Unfortunately, while Hammerstein helped kickstart Sondheim’s professional career — convincing him to write lyrics for West Side Story and Gypsy even though Sondheim initially wanted a project where he could write music and lyrics both — he passed away before he could see his student truly come into his own. Hammerstein died in 1960 on his farm in Doylestown. Two years later, A Funny Thing Happened on the Way to the Forum opened on Broadway, for which Sondheim wrote both the music and lyrics. It won the Tony Award for Best Musical. 

Sondheim Pays It Forward 


“Sondheim made it very clear that one of his priorities in life was being a teacher and passing on knowledge and encouragement and doing what Oscar Hammerstein did for him,” theater historian and producer Jennifer Ashley Tepper tells InsideHook. “It’s so remarkable to think that Oscar Hammerstein mentored Sondheim, and certainly helped other people, but the breadth of people that Sondheim mentored was just so huge.” 

After getting his footing in the theater, debuting as a composer-lyricist with Forum and then working with Richard Rodgers on Do I Hear a Waltz?, and then hitting his stride in the ‘70s and ‘80s, his most productive period, which started with Company in 1970 and ended with Assassins in 1990, Sondheim gained a reputation as an artist with something of an open mailbox policy. If you wrote to him, chances are he would write back, offering advice, answering questions and being generous with his time and expertise.

However, his goal as a mentor wasn’t simply one of volume. As Tepper explains, he had a “hefty” mentorship with Lin-Manuel Miranda (of Hamilton and In the Heights) and Jason Robert Brown (Parade, The Bridges of Madison County, The Last Five Years), as well as the late Jonathan Larson. 

“I remember reading one letter that Jonathan wrote to Sondheim where he was like, ‘I’m starting on a new rock opera and I’m working on it passionately’ … and that was the beginning of Rent,” says Tepper, who was the historian consultant on Tick, Tick … Boom! and creator of The Jonathan Larson Project. Sondheim was likely one of the first people in the world to know about Rent, the ‘90s rock musical that changed the landscape of Broadway, which to Tepper shows “the depth of their correspondence and the depth of Sondheim’s mentorship toward Jonathan.”

Here again the Broadway lore creeps in. The movie Tick, Tick … Boom! depicts Sondheim as an encouraging but not quite hands-on figure in Larson’s life. As Tepper fact checks, his helping hand cannot be understated: Sondheim responded to Larson’s letters offering advice, he wrote letters of recommendation, helped him get awards that kept him afloat, helped him get a big-time agent (which isn’t the case in the film). He even let Larson sit in on rehearsals for the original production of Into the Woods in the ‘80s. What up-and-coming composer wouldn’t want to be in that room?

“Unexpected significant moments, moments which happen entirely by chance, keep life surprising and sometimes change its direction permanently — not events, mere moments,” Sondheim wrote in Look, I Made a Hat. “My parents’ divorce, for example, was an event: it led to my meeting Oscar Hammerstein II and finding a channel into the work I was meant to do.” 

There it is: Sondheim admits the whole notion of being a geologist, or whatever Hammerstein happened to be, was bogus. He was meant to create theater. And yet, would we have had the Sondheim we cherish today, with a catalog of shows and songs that continue to surprise audiences time and time again, without a mentor who cared as much as Hammerstein?

Sondheim’s devotion to mentoring the next generation, even at the expense of his own work later in life, seems to answer that question quite clearly.