Lin-Manuel Miranda was reading Ron Chernow’s Hamilton on vacation, goes the fable of the year, when he was struck with inspiration. Later, at the first public performance of a song from his musical, he told his audience at the White House that Alexander Hamilton was “someone I think embodies hip-hop.”

Are you fucking kidding me, I thought, 20 minutes before seeing Miranda’s finished musical for the first time, on its closing weekend at the Public Theater downtown. What kind of maniac would connect those dots, and also expect it to work, given the long history of stodgy classicists attempting to harness hip-hop’s free-wheeling essence and only marginally succeeding at best? I thought about bailing on my friend, who invited me as his plus-one. I went because I didn’t want to be rude, but I still complained when I discovered its length (nearly three hours).

Seven months later, I’m that fuckin guy who won’t shut up about Hamilton; surely you know one, or are one, or have read one (or many) on the internet. But as vehement and true as my adoration for the musical and its creator may be, I still couldn’t fathom how anyone—even a dude who, like me, had grown up on a very specific era of pre-internet hip-hop—would be sitting there on the beach, reading an 832-page tome about a founding fucking father, and be like, oh yeah, eureka, this is a story that should be told through the medium of a rap musical. Sure, sure.

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In my quest to understand, I read Chernow’s book (on my phone, which I do not recommend) and took down some parts that felt particularly relevant to hip-hop. Throughout this journey, conducted over half a year, I sought to parse the most illuminating, tangibly hip-hop parts of the book Hamilton by 66-year-old historian Ron Chernow. I’ve focused on the first quarter of the book because that’s where most of my revelations occurred, and also because the screenshots were too numerous to compile in their entirety. (On an iPhone 5, 832 pages become 3941.) All emphasis mine.

On the mother of Elizabeth Schuyler, who would become Hamilton’s wife:

The wary Frenchman decided that it was “best not to treat her in too cavalier a fashion” and concluded that General Schuyler was “more amiable when he is absent from his wife.”

This struck me as analogous to the player narrative that’s such a cornerstone of rap philosophy (later, though, Chernow explains that Mrs. Schuyler was probably just pissed off because she was pregnant with her twelfth child at the age of 47 and well, isn’t that just like a man). The fact that her husband, the General, was “more amiable when he is absent from his wife” seems like a line Future might write, only about himself. Or, perhaps closer to Lin-Manuel Miranda’s stylistic leanings, it shares a sentiment Jay-Z expressed about a man 300 years after Mrs. Schuyler wearily popped out her kid. Was Mr. Schuyler another “Big Poppa”?

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Earlier in the year, when [John] Laurens had tried to secure Hamilton a post as a secretary to the American minister in France, Hamilton had analyzed his own rejection thus: “I am a stranger in this country. I have no property here, no connections. If I have talents and integrity... these are justly deemed very spurious titles in these enlightened days.” These disappointments only buttressed his belief in meritocracy, not aristocracy, as the best system for government appointments.

In other words: all Alexander Hamilton had were balls and his word—exactly like the Geto Boys, via Scarface, via Scarface—but he had to struggle harder than most because postcolonial America was full of suckas and haters...

“The truth is I am an unlucky honest man that speaks my sentiments to all and with emphasis. I say this to you because you know it and will not charge me with vanity. I hate congress—I hate the army—I hate the world—I hate myself. The whole is a mass of fools and knaves... Adieu. A. Hamilton.”

...Or, fools and knaves, in the parlance of the time. Hamilton, in this excerpt, is at a particularly low point during the Revolutionary War, disgusted and disappointed by the state of things. He adopted and accepted a sort of separatist weariness. But his aspiration for the country was never far, and so in both his impulses to isolation and optimism Hamilton was not dissimilar from Nas, particularly in his younger days. “If I Ruled the World” would have practically been Hamilton’s theme song.

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Parts of his letter were sophomoric, with Hamilton making bawdy references to the size of his nose—jocular eighteenth-century shorthand for his penis—but much of it was thoughtful, showing that Hamilton had given serious consideration the the elements of a stable marriage:

She must be young, handsome (I lay most stress upon a good shape), sensible (a little learning will do), well-bred (but she must have an aversion to the word ton), chaste and tender (I am an enthusiast in my notions of fidelity and fondness), of some good nature...

I want a girl with extensions in her hair. Bamboo earrings, at least two pair. A Fendi bag and a bad attitude. That’s all I need to get me in a good mood...

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Hamilton and Laurens shared an idealism about the Revolution that yoked them tightly together. They were both unwavering abolitionists who saw emancipation of the slaves as an inseparable part of the struggle for freedom as well as a source of badly needed manpower. “I think that we Americans, at least in the Southern col[onie]s, cannot contend with a good grace for liberty until we have enfranchised our slaves,” Laurens told a friend right before the signing of the Declaration of Independence. This represented a courageous stand for the son of a very significant South Carolina slaveholder.

Having seen Hamilton twice, it is now difficult to envision Alexander Hamilton and his best friend John Laurens as not being two Puerto Ricans from New York (in the musical they are, respectively, Miranda and young boo Anthony Ramos). But in an era so barbaric that the enslavement of black people was rarely questioned, it is remarkable that they—two white men from New York—were so staunchly abolitionist, nearly a hundred years before abolitionism really picked up much steam as a movement among whites. That notion of political vision and contextually renegade spirit is central to the liberation-focused tenets of hip-hop.

Also parallel with hip-hop tenets, this line:

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“For God’s sake, my dear sir,” Hamilton wrote to one colonel when authorizing him to collect wagons, “exert yourself upon this occasion. Our distress is infinite.”

Alexander Hamilton had a way with words. This is the 1780s equivalent of saying “Get off your broke ass, son.”

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The Pennsylvania Evening Post inserted this item: “Captain Alexander Hamilton, of the New York company of artillery, by applying to the printer of this paper, may hear of something to his advantage.”

This passage was in fact about George Washington appointing Hamilton as his aide-de-camp, but it reminds us that not only was Ham a writer not a biter, he was also the first person in American history to quite literally print that paper. And he had other skills:

[Hamilton] was able to project himself into Washington’s mind and intuit what the general wanted to say, writing it up with instinctive tact and deft diplomatic skills. It was an inspired act of ventriloquism: Washington gave a few general hints and, presto, out popped Hamilton’s letter in record time. Most of Washington’s field orders have survived in Hamilton’s handwriting. “The pen for our army was held by Hamilton and for dignity of manner, pith of matter, and elegance of style, General Washington’s letters are unrivalled in military annals,” wrote Robert Troup.

Alexander Hamilton was literally George Washington’s ghostwriter, yo!!!!

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“Such is my opinion of your abilities as a critic,” Hamilton addressed him directly, “that I very much prefer your disapprobation to your applause.” As if Seabury were the young upstart and not vice versa, Hamilton taunted his riposte as “puerile and fallacious” and stated that “I will venture to pronounce it one of the most ludicrous performances which has been exhibited to public view during all the present controversy.” This slashing style of attack would make Hamilton the most feared polemicist in America...

He had such a way with words, in fact, that he would destroy you in the cypher. (One can see why Miranda, a skilled rapper who’s long built a side-hustle from freestyles along with George Washington, would be intrigued by this quality in a founding father.) And, like Jay and Biggie did so often, Hamilton was just out here freestyling, unleashing his “slashing” style as a matter of course. (Lin-Manuel Miranda has said that he was drawn to the story in part because Hamilton reminded him of Tupac.)

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At the White House performance, Miranda noted that Hamilton “caught beef with every other founding father, and all on the strength of his writing; I think he embodies the word’s ability to make a difference.” (He also had a close friend by the name of Hercules Mulligan, which is the best rap moniker that never was; Hercules Mulligan was kind of like Hamilton’s Beanie Siegel.)

For me, though, there was one very specific passage in Alexander Hamilton that was my eureka moment—the passage that made me realize what really compelled Miranda to go in such an non-obvious direction with it. It’s very short and, really, encompasses the feasibly small group of people whose interests include both reading historical texts figuring out how a nerdy freestyler from uptown would think to turn them into a musical, and Mobb Deep. (Thus far this is a group of one, but holler if ya hear me.) It is this:

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With peculiar zeal, [Hamilton] collected money owed to the firm. “Believe me Sir,” he assured the absent Cruger, “I dun as hard as is proper.”

“I dun,” wrote Alexander Hamilton, “as hard as is proper.”

“I dun as hard as is proper.”

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To Mobb Deep fans, and presumably anyone who grew up in Queensbridge in the 1990s, “dun language” is a slang style popularized by the rap duo in which “s” pronunciations are replaced with “d.” So “son” becomes “dun,” “solo” becomes “dolo,” etc; in 2011, rapper Prodigy told Karmaloop TV that it originated with their friend Bumpy, whose speech impediment meant that he naturally pronounced “son” as “dun.” Mobb Deep is probably my favorite rap group of all time, and Prodigy my favorite rapper and trendsetter (in addition to listening to his music, I recommend reading his autobiography and then listening to him read it again on audiobook). Obviously, “I dun as hard as is proper” spoke to my heart. Alexander Hamilton dunned hard, but he dunned only as hard as was proper, which is to say he was understating how much he dunned—he dunned, no doubt, enough to knock ya block off.

I’m not entirely clear how Hamilton meant the term “dun”—the online dictionary I’m using is woefully sparse on late 1770s context clues—but the way he put it, with such deadly flair, also mimicked the phrasing and wordplay of Prodigy. He opens 1996’s “Front Lines (Hell on Earth)” by rapping:

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Yo, the saga begins, beget war

I draw first blood be the first to set it off

My cause, tap all jaws lay down laws

We takin what’s yours we do jerks rush the doors

Here come the deez tryin to make breeze and guns toss

That’s where it clicked fully for me, as Chernow described the harrowing feats of bravery and desolate landscape among which Hamilton had to help lead the Minutemen to victory during the Revolutionary War: the portrait Hamilton painted was as bleak as the one Prodigy created for his own surroundings, and the verbiage was just as dramatic, as vivid, as impactful, as true to this great nation’s ever-sanguine struggle.

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In creating Hamilton, Lin-Manuel Miranda trusted in his own instincts and took a massive leap of faith with them. However unlikely, he ended up turning 18th-century history into one of the most important cultural artifacts of 2015 and—as my colleague/fellow rap nerd Timmhotep Aku put it—“reaffirmed that hip-hop is as American as apple pie.” I thank him for that.


Contact the author at julianne@jezebel.com.

Image via AP.