Five Storytelling Lessons From Hamilton’s America

(Note: art of Leslie Odom, Jr. as Burr done by the inimitable Amy Houser, who did the cover for Irregular Creatures. You can find Amy’s Twitter here, and her website here.)

I was going to write a post about The Walking Dead. I don’t watch that show anymore, but even without watching it I’m roughly abreast of what’s going on there because, ha ha, social media can’t shut its mouth for 60 seconds, much less 60 minutes, and so I know who Negan killed in the opener of the current season. (Spoiler warning: Negan kills all our hopes and dreams.) And I wanted to talk about why I don’t watch it anymore, why I think the show has become something approximating PAIN PORN, why I think it’s gone too far down the rabbit hole of FEEL BAD TV, why I think it’s all pure surface now and has very little deeper going on — and, above all else, why I believe the entire conceit of the series summons my disbelief.

But, y’know, c’mon. I’d rather not waste my time or yours — plus, some people continue to love the show, as they should. Love what you love, and don’t let me pee in your pool. I mean, I already peed in your pool, so it’s too late on that particular front, but I mean, metaphorically, I don’t want to urinate in any of your cherished psychological spaces.

Instead, let’s talk about something I like.

Let’s talk about Hamilton.

Or, more specifically, the so-called Hamildoc — Hamilton’s America, a PBS program detailing both the rise of the musical and the history that forms its bones and its blood. As noted, I came to Hamilton late — I was particularly hesitant to listen to the musical once I discovered it had little to nothing to do with actual delicious ham. And once I did listen to it, I listened to it the wrong way: a slap-dash listen where I dicked around on the Internet as it played. Once I finally ceased all such dicking around, and once I sat with it and listened to it straight through, any resistance I had was sandblasted away. The musical planted its seeds. I still hum and sing it daily. My wife does too, now. In the car, the five-year-old-known-as-B-Dub will ask to have either Star Wars put on the radio — or Hamilton. (He also likes to use the name “HERCULES MULLIGAN” as his battle cry. He’ll just bust into a room, fists up, muscles out, and he’ll growl, “HERCULES MULLIGAN!” because he’s pretty sure that’s the best name of all time.)

So! I watched the doc with glee straining the ventricles of my poor mortal heart and I was not disappointed. More importantly, though, I took home a number of storytelling lessons as I watched it — because to me there’s nothing more fascinating than watching an interesting creator in the process of creation, and Lin-Manuel Miranda is nothing if not a very interesting creator, indeed. To be able to watch the genesis of the musical and the unfolding of the narrative was not only fascinating — it was informative.

And thus I present, five storytelling lessons I grokked from the doc.

Do with these as thou wilt shall be the whole of the law.

It Takes The Time That It Takes

It took Lin-Manuel six years to write Hamilton.

It took him two years to write the first two songs.

I think we have this idea in our heads that creation has to be fast and furious, that it’s either pyroclastic fucksplosion time or it’s nothing. And sometimes it is! Sometimes writing something is like having an INSPIRATION GRENADE shoved down into your undies and then it detonates, and the only thing you can do is ride the shockwave to a finished piece of something.

But sometimes, inspiration comes in threads. A red thread here, plucked out of the air. An orange thread there, found wound around your pinky. You find these threads over time and only over time do they start to come together into a proper rope to climb. I tend to write pretty fast, but Blackbirds famously took about five years. Atlanta Burns was a book that had all these separate parts that took a year or more to come together. Exeunt (recently announced!) has been in my head for about two years and it was all these ill-fitting but interesting pieces that needed just a few more bits and a couple dollops of creative glue to bring them together.

Point is, it takes the time that it takes.

It takes a week, a month, a year, six years.

The brownies gotta stay in the oven till they’re done, son.

Read Broadly, For Inspiration Is Fucking Weird

Lin-Manuel found the inspiration from Hamilton in Ron Chernow’s book. At least, that was the match that lit the powder keg — Miranda was sitting on an explosive barrel packed with hip-hop culture and historical musicals and his own life (and his own father’s life, too). There is an astonishing creative alchemy there, but it only happens when you let it. When, in a sense, you force it — or, rather, you maximize conditions. As I am fond of saying, lightning strikes are rare, but only because we try to avoid them. If you want to get hit by lightning, you can swaddle yourself in metal foil, grab an umbrella, and run out into a storm.

Miranda isn’t absorbing a creative diet of only other musicals. That’s part of it. But it’s also his life. His experience. And then it’s also about reading broadly. Go beyond the fence. Leave the comfort of the town and head out into the woods where unexpected books offer unanticipated mystery — and, better yet, unseen inspiration. Exeunt for me only started to come together when a few non-fiction books added the bridging components, bringing context to these disparate ideas. (I won’t say what books because, well, that’d spoil the story a bit.)

Let Your Fear Of Mortality Drive The Car Once In A While

Both Alexander Hamilton and Lin-Manuel Miranda were driven by a fear of mortality. What days you have, what days you don’t, and how you choose to fill them. There’s no great lesson here except that, I think, fear of mortality is exceedingly common, as it is the one thing we literally all share. We all share that end. And you can be hamstrung by that.

Or you can use it.

There is an energy to that fear, if you can seize it.

You can use that energy to create. To fill your life with purpose.

Don’t wait. To wait is to die. (Just ask Burr.)

Just Write The Parts You Need

In the doc, Miranda is talking to Sondheim and Weidman about writing historical musicals, and Weidman recalls telling Miranda some pretty simple — yet amazing — advice. When talking about how much research and history there is to absorb, and further how to distill that down into a musical, Weidman said: “Just write the parts you think are a musical.”

*mind asplodes*

I can’t tell you how freeing and how clarifying that is. Not just about musicals, but about whatever you’re writing. Just write the thing you’re writing. If what you’ve got is not the thing you’re writing? Then scrap it. Write what you need. Keep what suits the work. You owe the story — and the audience, eventually — only that.

Dig Into Deeper Dirt

If you play Minecraft, as I have and as my son does now, you learn that the deeper you go, the better resources you find. You start to find coal and iron — then, deeper still, you’ll find gold, and even further down, you’ll find diamond. It’s a good metaphor for the act of creating a story, I think. Most of a story exists on the surface or near it, and that’s okay. It should. It can’t spend all its time down there in the dark.

And by “in the dark,” I mean in the loamy silt or hard schist of theme, metaphor, and motif. These components are often invisible, but can be sensed —

And, with repeated reads or listens, excavated.

Part of what’s great about Hamilton are those repeated listens. Listen again and again and you begin to find things you didn’t find the first — or the second, or the eighth — time through. You find flecks of gold and the hint of diamonds down there in the narrative, little character and story bits you missed, interesting turns-of-phrase or better yet, unrealized turns-of-narrative. And then you watch the doc and you see even more: like the way “Burn” takes a historical element and makes it a symbol of her character at that point. Or how the rap styles evolve throughout the work and through different characters. Or how Jefferson’s been gone away so long, he’s figuratively missed the cultural advancement into hip-hop storytelling and so his introduction is jazzier, older, out-of-touch. Lin-Manuel doesn’t shine too bright a light on those things; he has them there if you want to find them. No trail of breadcrumbs. No sign saying DIG HERE. But if you dig, you might find these bits over time.

And that’s vital for a storyteller. As I said, most of a story lives on or near the surface. But a lot remains invisible, and that doesn’t necessarily happen accidentally. That’s something you put there. These are things you hide in the dirt, unseen yet discoverable. Deeper thinking about what the story means, who these characters are, even how the mechanism of the narrative relates to the events of the narrative — that’s huge. Not only does it give the tale a stronger backbone, but it also rewards the audience who revisit the work.

It rewards the audience who grabs a shovel and digs.

Bonus Round: The Two Truths Of Every Character

I know, I said five, and this is number six.

I’m a writer, not a mathematician. Shut up.

In the Hamildoc, we see one thing discussed again and again in relation to these (very real, very historical) characters, and that is how they are both beings of light and darkness. They are angels and devils at the same time. Washington and Jefferson are the architects of this nation and of the freedom we enjoy, and they both also owned people. They both somehow believed all men are created equal while simultaneously demonstrating how untrue that was for them. Hamilton is driven by his own manic genius, but his heroism in the first half of the work burns him out, and soon he becomes grist for the tragedy mill by the second half. Burr is a villain in our history books but the culmination of his villainy is given context and empathy throughout. We see two sides of him as we see two sides of most of the characters. As Miranda notes in the doc: none of these people are saints. And, I’d argue, none of them are truly villains, either.

People are rarely all good or all evil. That’s true of characters. It’s true of people. People routinely do great things while believing bad ideas — and they do bad things in support of pure ideals. In this age of political bullshit, it’s important to see people as people, as wildly imperfect creatures. And as a writer, that’s vital. Every character is seeing themselves in a broken mirror. Every character is complicated and flawed — often to different degrees depending on the type of story you’re telling, sure, but flawed just the same.

It’s good advice for storytelling. And it’s not terrible advice in life, too.

*salutes Alexander Hamilton*

*salutes Lin-Manuel Miranda*

Your Obedient Servant,

C. Wen

(Note: you can watch Hamilton’s America in full right here.)


  • I loved that documentary, too – more than I expected. It is, frankly, the best one I’ve seen. Our daughter has been singing the soundtrack non-stop for months – it was AWESOME to learn the story behind it, and see the actors and how they visited sites, explored characters, brought history alive. And yes, Lin-Manuel Miranda? Genius. I could not believe how he persevered.

    Your delving into the storytelling lessons? Also genius, and will re-watch with this in mind. Thank you (as always).

  • Can’t recommend the Chernow enough – just a fascinating read. The show’s amazing as well – I was lucky enough to win lottery tickets in August. So incredible.

    • Also something LMM tweeted a while ago that wasn’t mentioned in the doc – the ‘Whoa-ohh-ohh-oh’ cadence in ‘My Shot’ is the same as the sign-on noises from using a dial-up modem to sign onto AOL, because he wanted to show that the world was changing. ::mind kerblooey::

  • Chuck, I’ve spent so much of my adult life feeling bad for not being a faster writer, even feeling like I must be failing because I can’t write quickly with the kind of feverish pace I imagined must come from inspiration.
    And it wasn’t until I read some of your essays on writing that I finally realized that it’s OKAY to be slow. And easing up on myself, accepting that I can take my time and be a slower writer and that it’s totally NOT failing has been a life changer.

    Suddenly what I thought was “writers block” has changed into slow and steady progress. I can’t thank you enough for this insight. Lin is right. You’re right. It takes the time it takes.

  • Chuck, given the current emotional climate in this country, I couldn’t be better pleased that you chose to write about something you love. That in itself would have brightened my morning, but you did it so bloody eloquently! I stopped seven or more times just to admire how beautifully crafted individual sentences and sentiments were. You were clearly inspired. Now I’ve got “glee straining the ventricles of my poor mortal heart.” Thanks!

  • Great post. Completely agree about TWD, so much so that I didn’t even watch last night and I DON’T CARE (but nobody tell me, I don’t want to know). And I’m really glad you wrote about Hamilton–such an amazing feat of storytelling and songwriting we can all learn from.

  • I love Hamilton. And the doc. If you haven’t seen it, there’s also a book called Hamilton: The Revolution which has all the lyrics, interviews with the actors, and annotations by LMM. It is AMAZING and highly recommended.

  • Glad you gave the show a listen, Chuck. Like you, I found some great writing lessons in the Hamilton documentary. Also in the tome that contains the lyrics, as well as in LMM’s amazing lyrics. I hadn’t distilled the lessons down into anything quite as neatly stated as you did here, so thank you for giving me a short, sweet list that I can look back to when the writing feels hard. And slow. And frustrating.

  • As someone obsessed with Hamilton, I love this post. I’ve seen the musical, listen endlessly to the music, read Chernow’s biography, own the “Hamiltome” (Hamilton: The Revolution), and now have seen the Hamildoc. For me as a writer, this obsession is a master class in creativity and tenacity. First, Miranda found himself an incredible story with Hamilton, whose meteoric rise and equally impressive fall from grace make for great drama. Then he thinks outside the box by taking a hip hop approach to the music — and it works so unbelievably well! The supporting characters, especially Burr, are equally compelling in their complexity.

    I’ll add one note to this post: Miranda emphasizes that he conceived the idea for Hamilton while on vacation. He reminds people to “take a break” now and then. Hamilton didn’t, and look where that led him! If we take care of ourselves as artists and creators, our work will be richer as a result.

    Thanks for giving me a place to expound on all things Hamilton. My family is sick of hearing about it. 🙂

  • Boom.

    I only wish that they’d delved more into the casting choices they’d made, because that adds an even richer, deeper layer to the overall story.

    Stylistically, storytelling, character, theme, structure, music, libretto–Hamilton is something that writers should be eagerly unpacking because there are SOOO many rich layers to it. It should enter every writer’s cannon of what to look at not just as a “finished product” but as a “how to” in terms of creating.

  • Of course I would come here to find you having covered the documentary. Why am I even surprised?
    Great read.
    Hamilton is what sparked my love for writing and really fully diving into it again after a period of half-assery. Thanks for putting things into words that I wasn’t yet done reflecting on because I suffer from squirrel brain atm.

  • October 25, 2016 at 8:22 AM // Reply

    Watched the doc with my oldest (teenage musical theater nerd) and I was dorking out as hard as she was. Seeing someone else’s process is always fun and HERCULES MULLIGAN — best name ever.

  • I’m just gonna shitpost my support and say “this is some inspirational shit.” I got nothing to add to the convo. I just want to see more shit like this shit, so thanks.

  • With all the superhero movies and shows lately which feature “perfect” perfectly flawed characters, it’s nice to see someone willing to admit that characters do bad things. It is what it is.

Speak Your Mind, Word-Nerds