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II IN WHICH TOMMY KAIL IS INTRODUCED and HIS ADVENTURES with LIN SURVEYED

For two years, nobody heard anything new about The Hamilton Mixtape, because there was nothing new to hear. Lin got absorbed in other pursuits. With Tom Kitt and Amanda Green, he wrote the score to the stage adaptation of Bring It On, directed by his Heights choreographer Andy Blankenbuehler. He did Spanish translations of the Sharks’ lyrics for a Broadway revival of West Side Story. He wrote a rap during the Tony Awards telecast that the host, Neil Patrick Harris, delivered to close the show. He married Vanessa Nadal, a scientist (now lawyer) he had met back in high school. (When they met again after college, they bonded over Grand Theft Auto and Jay Z. He calls her the smartest person he knows.) He turned 30, then he turned 31. One constant in these years was Freestyle Love Supreme, an improv hip-hop group that must be seen to be believed. Taking suggestions from the audience–a word, a story–Lin and three or four other rappers create routines on the spot: inventive, hilarious, and often moving. In June 2011, the founders of Ars Nova, an adventurous theater on Manhattan’s West Side, asked the group to take part in their annual benefit. Instead of doing their usual rap-by-the-seat-oftheir-pants improvisation, the group’s members decided to perform songs they had written ahead of time, for projects they’d been working on separately.

Lin wavered between two options. In what would turn out to be an exceptionally lucky break for musical theater, he decided against “Baked to a Crisp,” his song about adolescent pot use, inspired by a Junot Diaz story. Instead he chose to premiere the second song from The Hamilton Mixtape.

“My Shot” is, in the lingo of musical theater, an “I want” song. These are the numbers that appear early in a show, when the hero steps downstage and tells the audience about the fierce desire that will propel the plot. Think of West Side Story, when Tony sings “Something’s Coming,” or My Fair Lady, when Eliza sings “Wouldn’t It Be Loverly?” Without a song like this, you wouldn’t get very far in a musical: A character needs to want something pretty badly to sing about it for two and a half hours. And you wouldn’t get anywhere at all in hip-hop. For all of its variety of style and subject, rap is, at bottom, the music of ambition, the soundtrack of defiance, whether the force that must be defied is poverty, cops, racism, rival rappers, or all of the above. Think of Nas’s “The World Is Yours,” 2Pac’s “Picture Me Rollin’,” or Eminem’s “8 Mile.”

Like the rappers who performed those songs, Alexander Hamilton lived hard, wrote fast, and hustled his ass off. “For to confess my weakness, Ned,” he wrote to a friend at age 14, “my Ambition is prevalent.” This man was born to perform an “I want” song. Which is not to say that “My Shot” was easy to write. As Lin moved from project to project after his White House performance, the song lurked, semi-finished, in his notebooks. He wrote and rewrote, trying to capture Hamilton’s sprawling ambition in beats and rhymes. It took more than a year to get it right. When the time came to perform it– when Lin stepped forward as Alexander Hamilton himself for the first time–he learned that writing it had been the easy part.

At Ars Nova that night, Lin took the stage with Chris “Shockwave” Sullivan, another member of Freestyle Love Supreme. Chris began to beatbox. Lin began to rhyme. He managed only a few bars before he got tangled in his words. He had gone way, way too fast.

Lin waved Chris off. He told the crowd that he needed to start over. They loved it, which didn’t make him feel any less horrible.

Chris started beatboxing again. Lin took it from the top, but slower. He nailed it: three dense minutes of rapping about Hamilton’s plans for his ascent, and the country’s. The crowd loved it even more.

Out there in the dark, cheering with the rest, sat Tommy Kail, the director of Freestyle Love Supreme and In the Heights. Lin had been telling him about Hamilton for three years at that point, beginning with the g-chat messages he had sent from Mexico while reading Chernow’s book. Tommy could tell that “My Shot” left the audience hungry to hear more of Hamilton’s story; he certainly felt that way himself.

When the performance ended that night, everybody trooped upstairs to drink and mingle. Tommy found Lin, and told him that he should get serious about developing the Hamilton project. They both should.

What does a theater director have to do with a hip-hop album? Plenty. Tommy wasn’t just the guy who staged Lin’s material. He had become a close friend and something like an artistic confidant. Tommy had started a theater company after graduating from Wesleyan. A friend from school suggested that he consider producing a grabbing the mic at family functions, imagining himself show by Lin, who had been a freshman when Tommy was a senior. (They’d never met, and their closest brush hadn’t gone well). Tommy was annoyed that people kept showing up at the theater where he was working to take lights and other gear for the sake of some freshman’s musical.) In June 2002, they had their first meeting to talk about the show that would become In the Heights. Somehow, in the course of that conversation, one of them started quoting a legendary verse by Big Pun–“Dead in the middle of Little Italy little did we know / That we riddled some middle-men who didn’t do diddly,”–and the other finished it.

“We cocked our heads at each other in recognition,” Tommy recalls. “It was like two dogs in the park going, Oh, you live in this neighborhood, too?’”

The shared love of theater and hip-hop led them to collaborate on Heights, and that collaboration revealed something far more important: The talents of each complemented the talents of the other. Growing up in New York, Lin had developed an instinct for the spotlight: grabbing the mic at family functions, imagining himself onstage whenever his parents could take him to a Broad-way show, giving free rein to a creative impulse that was inexhaustible, omnidirectional, sometimes counterproductive. (He and some friends got arrested once for busking on a subway platform. A well-placed friend of his father got him out.)

Growing up in Alexandria, Virginia, Tommy cared a lot more about sports than theater. He excelled at soccer and baseball, and thrived in the middle of the action. But in high school, his understanding began to outpace his ability. “I could see what was supposed to happen on the field, but just wasn’t able to do it,” he says. “I realized my role needed to shift.” That precocious insight, to recognize the talents of the people around him, and position himself accordingly, was a superb start to a directorial career. It put him in the ideal frame of mind to cross paths with a young writer who literally had more ideas than he knew what to do with.

At the Ars Nova reception, Tommy proposed that Lin start sending him Hamilton material on a regular basis. In fact, he thought they should aim to present a concert version of Hamilton songs in six months’ time. The room could be small, the stakes could be low–that didn’t matter. What mattered was setting a rou- tine of writing and feedback. Lin agreed.

Then, a few days later, the profile became very high indeed: Lincoln Center invited Lin to perform in the American Songbook concert series. Tommy thought it could be an excellent way to try out Hamilton songs, even though it put pressure on Lin to write and polish enough material to suit such a prestigious occasion. Still, how they could pass up this chance? Or, as Lin had put it for the first time that night at Ars Nova, how could they throw away their shot? Lincoln Center had offered them the Allen Room on the night of January 11–Alexander Hamilton’s birthday.