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Writerly Wisdom from Stephen Sondheim


Last week, Stephen Sondheim, one of our greatest musical legends, passed away at the age of 91. Although Sondheim was primarily known for his work as a Broadway composer, there is much more to his work than just creating the songs for musicals.


If Richard Rodgers and Oscar Hammerstein, II revolutionized the genre by weaving story and song together, Sondheim picked up the baton and carried it into the latter half of the 20th century, adding complex characters with lyrics that advanced their personalities and relationships into the mix.


The result is some of the most enduring and dynamic theatrical work ever created. Without West Side Story, Gypsy, Sweeney Todd, and other seminal productions, we wouldn’t have live theatre as we know it today.


I’ve been going to see musicals for so long that I can’t remember what my first Sondheim show was. However, memories of seeing individual shows quickly pop into my mind.


An outdoor production of A Funny Thing Happened on the Way to the Forum that left me in stitches even as the show ended. A rendition of A Little Night Music where the harmonies of the Quintet were of such perfection that I could have listened to just them and not the entire show.


The most memorable, of course, was seeing the 2007 revival of my favorite Sondheim production, Company, with the great Raul Esparza at the helm in the role of Bobby.


But when I collectively think about my memories of seeing Sondheim shows live, the characters are what resonate with me the most. Apart from Esparza (because he’s Raul Esparza for goodness’s sake), I remember not the actors’ performances, but how the lyrics and melody carried me into their individual worlds.


To me, that’s the greatest thing a writer in any genre can do: introduce you to the world of a person who doesn’t exist and make you care about them and know them as if they are flesh and blood.


It’s impossible to imagine theatre without Sondheim. Period. That’s what makes this loss so shattering to creative people.


91 years was indeed a long, fulfilling, beautiful life for him. But as a close friend of mine from college lamented on Facebook this weekend, that the fact that the person who wrote “I’m Still Here” from Follies is no longer here is agonizing.


This is the kind of impact an author should dream of leaving behind.


I know what you’re thinking. We literally just talked about Tick…Tick…Boom! and Hamilton last week and now you’re probably waiting for me to bust into Alexander Hamilton’s monologue during the duel scene (Legacy? What is a legacy?)


No, Creativity Matters is not turning into a Broadway blog. But I would be doing all of us a great disservice if I didn’t stop to pay tribute to the legendary Mr. Sondheim.


Even if you are not an obsessive theatre aficionado like me, you should still care because this loss matters to all writers, not just the playwrights and composers.


Having said that…here are some bits of wisdom the quotable, witty Sondheim leaves behind for you.


“The worst thing you can do is censor yourself as the pencil hits the paper. You must not edit until you get it all on paper. If you can put everything down, stream-of-consciousness, you'll do yourself a service.”


I don’t know about you…but the thought of one of the greatest writers and composers of all time struggling with self-sabotage and condemnation is really encouraging to me.


His words are a powerful reminder that none of his award-winning, genre-altering hit shows “just happened.”


Like any great work of art, they went through painstaking revision and reworking before becoming the masterpieces we know today.


Much of Sondheim’s own work is even a commentary on this fact, most notably in the show Sunday in the Park with George. The musical, inspired by Georges Seurat’s painting A Sunday Afternoon on the Island of La Grande Jatte, imagines its way into Seurat’s artistic process and psychology, particularly the battle between finding satisfaction in relationships and his creative work.

The very opening of the show makes evident the theme of producing great art. "White, a blank page or canvas,” Seurrat proclaims. “The challenge: bring order to the whole, through design, composition, tension, balance, light and harmony."


A writer—even Sondheim—faces this same beginning, this same challenge to bring order and beauty out of nothing. This wasn’t just something Sondheim wrote about because he thought it was cool. It was something he knew well, and clearly, the forcefulness of his words show that he wanted writers to understand it as well.


“If you're dealing with a musical in which you're trying to tell a story, it's got to sound like speech. At the same time, it's got to be a song.”


One of the great joys for me as a writer listening to Sondheim is how natural the lyrics feel and how perfectly they fit the character who is speaking. Each character has not just their own musical theme, but their own vocabulary, their own phraseology.


Sondheim has also been quoted as saying that all of the characters he wrote songs for came to him fully developed, ready to have music created especially for them.


While this is true in the sense that the idea for the show and often the script already existed, it’s also quite literally true for Into the Woods, a musical that creates an entire universe based on fairy tales and folklore.


The genius of Into the Woods is Sondheim’s ability to use music to create a unified world out of a collection of disparate childhood stories. It is primarily the music—the collective score as well as the individual characters’ songs­—that makes this happen.


The songs in Into the Woods do serious heavy lifting. They create a setting, set up conflicts, and tell the audience what they need to know about the characters—and it’s usually not what they expect.



Yet, like all Sondheim’s musicals, we get so caught up in the Into the Woods universe that the music becomes a seamless part of the characterization.


Every main character wants something, whether it’s Cinderella’s desire to go to the festival or the Baker and his wife’s desire for a child. We feel those desires intensely because of the role of music in the story.


Not all of us—perhaps very few of us—write musicals. However, whatever genres we do write in, our dialogue still has to sound realistic and it still has to accurately capture who our characters are.


“If people have split views about your work, I think it's flattering. I'd rather have them feel something about it than dismiss it.”


Getting good reviews always feels…well, good. It’s a stroke to your ego and an affirmation of your talent.


But too many good reviews with the absence of any constructive—or even unconstructive criticism—can have the exact opposite effect.


It makes you wonder what people aren’t telling you.


I have multiple five-star ratings on Amazon for my book, The Goodbye-Love Generation. That feels warm and fuzzy…but I didn’t feel like a real published author until I got my first two-star rating.


It meant that I’d created something people could have mixed feelings about, which made me feel powerful as a creator.


Sondheim obviously had a string of hit musicals throughout his career—far more than most. But one lesson he teaches writers is that not everything you create has to be a critical success. Even your perceived failures can still become critical parts of your body of work.

A great example is Merrily We Roll Along. Told with a reverse chronological structure that unfolds over a period of twenty years, it’s the story of three artistic friends as they experience the complexity, compromise, and betrayal that come with pursuing their dreams.


The original production premiered in 1981. To emphasize the youthful idealism of the central characters, it featured a cast of entirely teens and early-twenty-somethings. This was a good idea in theory, except that the actors lacked the seasoned talent of most Broadway performers.


Coupled with this issue was that preview audiences had trouble following the story, especially the jumps backward in time. To resolve this issue, the production company decided to have the actors wear sweatshirts emblazoned with the names of their characters.


Unfortunately, this only made the production appear even more amateurish, leading one reviewer to accuse Sondheim and company of dressing their cast up in “identical tracksuits.”


Another reviewer said that the show was “not merry,” “doesn’t ‘roll along,’” and featured “not even a glimmer” of the previous talent seen in Sondheim’s other shows. Merrily We Roll Along closed after fifteen performances.


Still, after multiple restagings and revivals in both the U.S. and U.K., the show is seen as a significant part of Sondheim’s body of work. In one particularly fascinating development, Richard Linklater, director of Boyhood, is making a film version starring Blake Jenner, Ben Platt, and Beanie Feldstein that will be filmed over a period of twenty years, then cut into the reverse-chronological presentation.


Sondheim’s words ring true for this and your own perceived failures: it’s better to have someone to have feelings about your work than have none at all.


The world may have lost Stephen Sondheim, but there is plenty of his wisdom to go around, enough for generations to come.


On Sunday, a crowd of performers from the Broadway community gathered in Times Square for a sing-along of “Sunday” from Sunday in the Park with George.


The video below is the perfect note to end on (no pun intended) in our exploration of Sondheim and his advice to writers. Plus, it features Lin-Manuel Miranda.




If you need some help taking a cue from Sondheim to put something—anything—on your blank page, my free Ultimate Writing Project Workbook is a great place to start.


It contains prompts, worksheets, templates, activities, and more to help you develop your writing and mine it for creative potential.


Request your copy here and I’ll email it to you, no strings attached.


Also…do you have a favorite Stephen Sondheim play, song, or character? Feel free to drop your own thoughts in the comments section.

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