5 Things Hamilton Taught Me About Story-Telling

Lin Manuel Miranda’s Broadway production of Hamilton did what few plays have; it broke the barriers between theatre and mainstream entertainment. Everyone is talking about it. Celebrities have collaborated together to make a mixed-tape based on it. 60 Minutes did a behind-the-scenes segment. Twice. Even my 15 and 16 year-old students are listening to the soundtrack. In fact, one student asked me if I would play the rap battle songs so she could study for a history quiz.

Well done, Mr. Miranda.

Needless to say, I had to listen. Once I did, I couldn’t stop. The story is compelling and the characters are complex. And even though the plot is about America’s beginning, it couldn’t feel more relevant to today. All this got me thinking about how Miranda told the story. And as Alexander said of himself about his desire to participate in the revolution, “Enter me, he said in parentheses.” My brain went into overdrive, and I analyzed the structure of the story. If you don’t mind spoilers, here are five things I learned about making a story more compelling:

Tell the story from a unique angle.

The play is called Hamilton, so it seems safe to assume that the play would be about Alexander Hamilton. And it is. Except he doesn’t tell his own story. The main narrator is Aaron Burr, Hamilton’s long time nemesis.


Think about it, though. If Hamilton told his own story, how interesting would it be. Someone way smarter than me once said that we understand other people by their actions and ourselves through intentions. If Hamilton had told his own story, every decision he made would be validated by his intentions and, therefore, would have little conflict that didn’t come off as whiny.

By using Burr as the narrator, Miranda creates immediate conflict. The audience gets a richer story and has a greater interest in following it to the end.

So, how can you as a writer implement this?

No, you don’t have to use your antagonist, villain , or otherwise evil dude as your baseline. But it is important to remember that stories need fresh perspectives. If you’re story is in first person POV, ask yourself who has the most to lose in your story, and put them at the mercy of the narrator. If you’re using third person, what new take can you employ to show the raw sides of your characters?

Even minor characters should have stakes.


I love quoting people smarter than me, so here’s another one for you: Every character is the hero of their own story. Angelica is Hamilton’s sister-in-law and is responsible for introducing her sister, Eliza, to him. As a result, Hamilton marries Eliza, so Angelica is important as she helps progress the plot. But that’s not what makes her interesting.

Angelica could easily have been shuffled off stage after her wedding toast to the happy couple. But then Hamilton would be a less interesting character. You see, Angelica was in love with him, but she knew it would be imprudent to marry him. As the oldest out of only girls, it was her job to find a husband that would keep her rich…erm, happy. Since Hamilton was an upstart at the time, she politely “gave” him to Eliza. And although Hamilton loves his wife, he alludes to yearning for Angelica when he gets into tough spots and is at his weakest. With this subplot, Angelica adds depth to Hamilton’s character while filling out her own.

If you have characters that feel underdeveloped, try getting to know them apart from how they interact with your protagonist. I like to have my characters clean out their closets, garage, purses, backpacks, etc. Then I spy on what they find, what they decide to keep and throw away and why they make those decisions. Then I bring that information back to their dealing with the protagonist. Most of the time, the clean out session information doesn’t directly make it into the story, but just knowing about it allows me to create more depth in them that makes it onto the page.

Foreshadowing done right creates all the feels.


Warning-Tissues people!

One of the songs in the play is called 10 Duel Commandments. In the song, the cast sings about the rules of engagement when someone insults another person. If an apology is not made or the offended cannot be satisfied in any way, a shooting duel is required to set things right. In the first third of the play, Hamilton and crew decide George Washington’s name is being unfairly dragged through the antebellum mud, so they conduct a duel on his behalf. The accused is wounded, but seems able to recover.

In the second third of the play, Phillip, Hamilton’s son, is likewise offended by a man spouting insults about his father. He challenges the loud-mouth to a duel and then consults his father on how to proceed. Hamilton councils his son to shoot into the air if no agreement can be reached. He proclaims if the other man is a gentleman, he will do the same. He didn’t, and Phillip ultimately dies of an infected wound.

This isn’t the worst!

Near the end of the play, Aaron Burr has had about enough of Hamilton for a multitude of complicated reasons, and they agree to a duel. If you are paying attention, you see the writing on the wall for Hamilton, even if you’ve never cracked a history book. Because Miranda’s use of foreshadowing tells us everything we need to know.

So how does this help you?

Once you’ve written your story, go back through your draft and decide how you can drop elusive hints that your readers will likely take for granted when they first encounter them but will have them beating their heads on their tables once they’ve read the climax. Try not to make them too obvious, or your readers will figure out what you’re up to and beat you to it. For example, if your character ends up trapped somewhere, maybe have them have to wear a too small coat or something that will show us how they react in tight situations. (Okay lame example, but you get the idea.)

Flawed characters are more interesting than perfect ones.

 burn hamilton alexander hamilton phillipa soo GIF

Alexander Hamilton was a great man who created many successful aspects of the American government. He was also a tool when it came to the women in his life. And the play is all the better for it. Because of Angelica’s love for Hamilton, and his longing for her, we know he may not be able to stay faithful to his wife. (Another point for Team Foreshadowing.)

Lo and behold, when he is left alone and under pressure, he succumbs to temptation. And is coerced into blackmail because of it. Double douche. And when he’s about to be exposed, he publishes a pamphlet proclaiming the entire affair, shaming his family right along side of himself. Triple douche. But this is better for the story, because how boring would the story be if he came to the colonies, helped win the Revolutionary War, and then helped run the country? We get that mythical being in our 8th grade textbooks.

But a man with desire for fame and flesh? Who has to overcome his own demons to gain what he wants most? Now we can identify. Try that on yourself. Imagine what you want most. Now, make a list of all the things you do to sabotage yourself from getting it. That makes you interesting. And also way more like the rest of us. Flaws make characters unique and much easier to root for.

The best thing you can do for your own characters is to put themselves in their own way. External conflicts are great, but internal conflicts keep the reader turning the page.

Music makes everything better.


Okay, so maybe this isn’t necessarily true for books. Wait a minute, yes it is. At least, sound makes everything better. One of the great things about this musical is its recycled lyrics. I know, initially that sounds lazy. But the genius is, even though the words are used repeatedly, the intent behind them is nearly always different. And the music underscoring the words denote differentiated emotions indicating growth, pain, and even victory…all the things we want for our characters.

Even if writers can’t use actual music in a story, we can immerse the reader in sounds. Yet another smart person once said that sound is the most under-utilized sense in writing. Try adding sounds to your scenes for depth. And if you’re brave, recycle sounds to produce memory links that result in emotional carry-over. Maybe one day while your character is on a picnic with the love of their life, they hear a particular bird chirping. Then later, when they are at the funeral for the same love, they hear the same type of bird chirping. Imagine the power of that memory!

And there you have it. Five things I learned about story telling from the play, Hamilton. If you haven’t had a chance to check it out, I highly suggest it. At the very least, listen to the brilliance that is the soundtrack. Your characters will thank you for it!



Teacher, writer, person. Mostly caffeine and sarcasm.

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