I’ve been listening to an increased amount of musical theater lately, perhaps because these long-form stories soundtrack my snow and WFH days so well. Regular albums rarely have the pull of a plotline, and podcasts and audiobooks often require a little too much concentration for multitasking. 

As I’ve streamed through the stories, I’ve found characters whose idiosyncrasies make me jump with recognition. I’m unlikely to organize a newsboy strike, found a fledgling nation, or rescue my love from the underworld. But I can certainly relate to the anxiety that these singing scribblers express as they try to sculpt words into something worth reading. Writing has the power to both build and destroy: why not examine that through words that can be hummed as well as read?

Katherine, Newsies

Even though I’ve watched and adored the film version of Newsies for years, I can’t tell you the name of our hero’s love interest. She exists; she’s in love with Jack; that’s about it. The Broadway version of the story, however, features a far less forgettable woman. While Katherine fulfills the role of Sarah (thanks, Wikipedia) as Jack Kelly’s love interest, she also fulfills the role of the film’s male crusading journalist. While Katherine still isn’t as rounded as I’d wish, she’s a charming addition to the cast. Her solo “Watch What Happens” has one of my favorite depictions of the writing process in musical theatre: “[This] could practically write itself— / And let’s pray it does, ’cause as I may have mentioned / I have no clue what I’m doing.” 

But beyond naturalistic depictions of doubts, this character also highlights the power of words to make a brand-new world. “Give those kids and me / the brand new century / and watch what happens,” she sings. Her words are the rallying cry of the newsies’ movement, the stone that topples the giant. By the closing number, Katherine’s writing has changed minds and policies for the better.

It’s an idealistic portrayal, for sure. But characters like Katherine can remind us how wonderfully words can turn the world upside down. 

Orpheus, Hadestown

In Hadestown, our writer heads beyond the upside-down and into the underworld. I’ve sung the show’s praises here on the post calvin before, so I’ll point you towards past Courtney for more on this Greek myth turned Tony winner. 

Hadestown portrays a much more nuanced concept of wordcraft than Newsies, and Orpheus’s writing has much more nuanced consequences than Katherine’s. Orpheus is working on the song that will bring spring again, “a song to fix what’s wrong / Take what’s broken, make it whole / A song so beautiful / It brings the world back into tune.” 

At first, this is what draws Eurydice to Orpheus: the way his songs brim with life and potential. But as time passes, Eurydice realizes writing is an obsession that blinds Orpheus to the coming cold. They need food, they need firewood if they’re going to survive winter, but Orpheus is more interested in his masterpiece. When he finally looks up at Eurydice, she has disappeared into Hadestown. 

Later in the story, Orpheus’s words become the chant that stirs up discontent against Hades’s oppression, and it even softens the tyrant’s heart for a moment. Yet Orpheus’s work is not the panacea for his world’s suffering. His story still ends in tragedy.

Alexander Hamilton, Hamilton

Lin-Manuel Miranda’s version of the Founding Father’s life also depicts writing as a source of both joy and tragedy. Hamilton’s manic productivity (“How do you write like you’re running out of time?”) catapults him into the highest levels of the new United States government. But his pace soon begins to create difficulties as well as opportunities. Just as Hamilton could “write [his] way out” of poverty, he can write his way into problems. He releases the tell-all Reynolds Pamphlet, imploding his marriage, and he sends passive-aggressive missiles to rival Aaron Burr, sparking a duel and his demise. 

When Eliza Hamilton sings “You built me palaces of paragraphs / You built cathedrals,” she grieves the jeweled reality of his lies, the destructive force of his pen. Writing, for A. Ham, is the stuff of both dreams and death. 

Jamie, The Last Five Years

No one dies at the end of The Last Five Years—but a marriage does. Sort of. We’ve known the characters’ fate since the show’s first song. Jason Robert Brown’s 2003 musical follows a reverse chronology: Jamie’s story travels towards the end of the relationship, and Cathy’s travels towards its beginning. Cathy is a struggling artist; Jamie is a bestselling novelist. Their careers draw them together and apart until the relationship itself crumbles.

Early in the relationship, Jamie’s writing uplifts Cathy into a place she can’t quite imagine for herself. He crafts the “Schmuel Song,” an allegorical story of a time-traveling tailor, to push her towards pursuing her dreams: “Shouldn’t I want the world to see / the brilliant girl who inspires me? / Don’t you think now’s a good time to be the ambitious freak you are?”

But while Jamie can create a world worth joining, he can also create a world to insulate himself from others. When he first meets Cathy, she’s the story he “should write” in life; as he wakes up beside someone else, he’s “changed the ending.” In their arguments, Jamie has told Cathy that he will not “fail so [she] can be comfortable.” His writing is the foundation for his success. And his writing will help him mold the world in his own image until she asks: “While he invents the world that’s passing by… / I’m a part of that / Aren’t I?”

Hamilton and Orpheus may have more traditionally tragic endings, but I’ve placed Jamie at the end because his story displays the carnage of his words so viscerally. In writing, in life, these are the questions that stick in our minds with the songs: are the worlds I’m creating with my words shared kingdoms, not isolated ones? And are they worth inhabiting?


What musical theatre piece would be complete without a playlist? If you’re interested, enjoy.


  1. Josh Parks

    I love this so much! There’s also the sheer chaotic energy of Sutton Foster as Jo March singing “The Weekly Volcano Press”: https://www.youtube.com/watch?v=IpsJf3hXh1A

    (Also I clearly need to check out Hadestown, since I literally wrote a master’s thesis on music and the Orpheus story.)

    • Courtney Zonnefeld

      This is my official kick to *finally* listen to the full Little Women musical: “The Weekly Volcano Press” is insane and wonderful. And I hope you enjoy Hadestown–it’s such a gorgeous, complex imagining of Orpheus’s story.

  2. Kyric Koning

    It’ interesting how most of your examples end in tragedy. People often don’t consider the consequences of their words. Words are quick and easy to slip out; words can lodge in minds and hearts; words can find places and listeners where they were not intended. And when written, they amplify these effects.

    As writers, it is important to view our words as positive, that they can and must change the world–but, we must also be willing to reconcile with the fact that things don’t always work the way we want and that there will be consequences. There always are.

    I adore this piece, by the way. A sucker for words, as it turns out.

  3. Chad Westra

    I’ve had a lot of mundane work lately, and have been listening to Hamilton and Les Miserables on repeat. I thought about writing a similar article, but you’ve done it brilliantly! And you’ve given me some new musicals to check out.

  4. Kayleigh Fongers

    I love this, Courtney! I think one of the main reasons why I love Hamilton so much is because of the exploration of words / writing. Eliza’s line that you featured here is one of my favorites. And I definitely want to check out these other musicals now.

    Also, speaking of Hamilton and writing, I once saw a tweet that said, “If Hamilton can write 51 essays in 6 months, you can write this one.” And it’s my new mantra for the post calvin deadlines now.


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