In the opening number of Broadway’s Hamilton, the character Aaron Burr raps, “Get your education, don’t forget from whence you came, and the world is gonna know your name.”

Three months after Hamilton’s premiere, Director Thomas Kail (‘99) returned to Wesleyan for a conversation at the Career Center on November 9th.

A History major while at Wesleyan, Kail’s theatrical credits include A Bus Stop Play (2007), Zusammenbruch (2008), In The Heights (2008), Broke-eology (2009), The Wiz (2009), Lombardi (2010), When I Come to Die (2011) and Magic/Bird (2012). Following his 2008 Tony nomination for In The Heights, he co-wrote the award show’s closing rap in 2011, performed by host Neil Patrick Harris. And, judging by the success of Hamilton this fall, the director is sure to be the front-runner of this year’s awards as well.

When asked “why Wes?” the former high school athlete from Alexandria, Virginia begins, “this is why guys,” before watching us erupt in laughter. “He’s old but he’s on Twitter!” He jokes. We laugh more.

In his four years at Wesleyan, Kail took precisely one theater class. As a kid, he didn’t see many plays, nor was he ever on stage.  “It never occurred to me that you could make a life in the theater,” he says. His freshman year at Wesleyan, instead of auditioning for film theses and Second Stage, Kail went to work on The Ampersand, where he was fired. “Carter Bays was the editor before me,” he says. “Little did I know he’d be one of the greatest humorists, and then there was me.”

Two years later, Kail was asked to help backstage for a friend's play through Second Stage. That spring, he went to study at Dartmouth on the Twelve College Exchange, where he lived in a freshman dorm, experienced the frat scene and sat in on a class with August Wilson. “I wanted to see if I could parachute into a place that was on the other side of things,” he says.

Back at Wesleyan, Kail wrote his senior History thesis on productions of Eugene O’Neill as exemplifying a change in American culture. Meanwhile, he directed his own Second Stage play, RE: Peter where he learned he was sharing the stage with a freshman production, Seven Minutes in Heaven. The freshman director was Lin-Manuel Miranda, Kail’s future collaborator on Hamilton and In The Heights.

Today, Kail calls Second Stage and student theater “absolutely essential” to his success. “I often think of Wesleyan as a hallway with a lot of doors,” he says. “Some of them ajar, a lot of them closed, but none of them locked.”

Most importantly, at Wesleyan that he learned about production. “The real core values of a producer are to get the resources together to go make something,” he says. “And I learned that at Wesleyan.”

And yet, as he admits, his college years weren’t all about cast parties and lunch in the CFA. His interest in theater only came as an upperclassmen and he spent most of his time living with soccer players. Today says how many of his friends pursued “normal” jobs.

“I’m interested in talking with people working in the arts and not working in the arts,” he says. “If you don’t have a life outside of the theater, you can’t have a life inside a theater. You have to go and fill yourself up.”

Upon graduation, Kail did as any self-respecting Wesleyan creative does: he swore he wasn’t moving to New York. “I also didn’t wear blue jeans and never saw Titanic,” he laughs.

Instead, he applied for a job at the Arena Theater in DC. “By the end of my senior year, I felt prepared and understood nothing was gonna be given to me.” The theater replied with a handwritten letter describing how all the applicants had MFAs in dramaturgy. “[HR] said, ‘if I hire you I’m going to lose my job,” he remembers. “‘But if you go get any job in theater I can make a case to the board.’’

So he found a friend of a friend’s father who worked for the American Stage Company in New Jersey and offered $100 a week for a PA. “Who you know is relevant,” Kail says. “But it’s not who you know in a fancy way.”

Arriving at his interview ready to talk about O’Neill and Re:Peter, Kail noticed the only thing circled on his cover letter was “P.S. I make a mean cup of coffee.” This was also the last time he put his GPA on his resume.  “Not that GPAs don’t matter,” he says. “You have to apply yourself and work hard to position yourself to know how to learn.”

One of the company’s questions? Had he ever driven a 15 person van. To which he replied: ‘‘Have I?’ “Which,” he says now, is technically not a lie. “It’s just two words I put together.”


So he got the job. 84 bucks a week, with taxes. 8 shows in 18 months. “I decided if I was going to mop the stage then I was going to do it as efficiently and as well as I could,” he says. “My pride in my work [remained], it didn’t matter what it was.”

When Arena called offering Kail a job, ASC offered him a promotion to Associate Creative Director. He was 23. “I would walk into meetings and people would think I was a proxy for my father,” he laughs.

Today, Kail explains that no matter what you do, you’re going to be overqualified in the beginning. “But you have to do the thing in front of you well. If you don’t do it, the rest of it doesn’t matter.”

While based in New Jersey, Kail would drop his actors off at 96th and West End and call his college friends to meet up. “I’d concurrently started a theater company in the city,” he says. In 2001, ASC closed and Kail was “forced” to the city.

Looking back, Kail is thankful he waited for New York. “The older you get, the more adept you get at tuning out all the noise,” he says. “Your instinct is the thing that has gotten you where you are right now. So if you learn to hone it, it will be how you choose your path.”

Naming his company Back House Productions, Kail worked with former classmate Anthony Veneziale (‘98), a former soccer athlete who brought Kail on to The Ampersand. Today, it's clear Kail prefers working with friends. “There are a lot of talented people in the world,” he says. “But you can find talented people who are kind and good and decent.” He refuses to work with people who are not. “Quality of person is more important to me than talent.”

At Back House, Kail got to be director. “Nobody under the age of 30 will be hired to direct,” he says. “So I hired myself. I made my 'yes' be louder than all the 'nos.” While he wasn’t paid, he kept side jobs going, including being an assistant actress Audra McDonald.

“My 20s were about saying yes to things so I could get better,” he says. “It was something that I learned at Dartmouth. Here are my wits, how do I take some of my skills and do my best. You put yourself in a situation where you can continue to learn and improve.”

In the spring of 2002, a Wesleyan friend sent Kail the script and CD of Miranda’s senior thesis In The Heights. Kail then asked Miranda to meet up in New York, eventually offering him a place in his company.

“I sat down with him in June 2002 and we never stopped talking,” he says. “It’s been a 13 year conversation.”  After two Broadway hits, Kail describes his relationship with Miranda as not only “deep” and “significant,” but “critical” to who he is today.

Together, they put on In The Heights at the Drama Book Shop Theater and eventually, five years later, reached Broadway’s Richard Rodgers Theater in 2008.  While they developed the show at venues around the city, Kail and Miranda also started Freestyle Love Supreme, an improv comedy/hip hop show with other actors from the musical.

“There was nothing promised with Heights,” Kail says.  “But it felt like it was time to jump. I wanted to walk into a room and say I was a director.”

Seated front row at Kail's talk was another Heights collaborator, playwright and professor Quiara Hudes, author of the play's novel. As she described, meetings with Kail happened everywhere from the playground in Central Park to the floor of her living room. "Tommy is particularly good at following the ‘what ifs,’” she says.  “If Lin had an idea on a new lyric, Tommy would think very quickly about ramifications.

As Kail explains, In The Heights was an opportunity to approach gentrification and “transcend just being a story about place.” Hence the  musical’s  international fan base. People want to see Heights because they want to talk about their communities adapting to great urban change. “I’m not in the business of giving answers,” Kail says.  “I’m in the business of asking questions”

Like his shows, there is something in Kail that invites conversation. I want to ask him to grab coffee, maybe even get invited to his New Year’s Party. But this is the Thomas Kail, and I should probably address him as “Sir,” and type a bit quieter while he talks.

His relationship to the audience is something the director has practiced. While at ASC, he got upset waiting for a college friend running 20 minutes late. It was then he realized he had no patience for daily life. “I think it’s important to find that balance of how you connect with your humanity.” He says. Especially, “if you’re gonna be a director.”

And, years later, Kail is definitely a director.

Hamilton, based on Ron Chernow’s biography, is described by the New York Times as “a rap-driven portrait of the rise and fall of Alexander Hamilton,” who, for those of us who slept through AP US History, was the first secretary of the Treasury.

Throughout the six years it took to get to Broadway, Kail faced the daunting task of “trying to create an envelope where this could exist.”  This being hip hop and the Founding Fathers.

His material meant 46 different pieces of music and about 60 different locations. “So we said no walls on stage,” he explains. “I had this image really early on that this was about witnessing history and the publicness and the privateness of that.” For inspiration, he turned to the open layouts of Thomas Eikan’s operating room paintings, as well as the plans of British parliament and Roman gladiator rinks.

“We wanted our company to absorb this story and also create a sense of unity with the audience,” he says.


And, keep in mind, while working on Hamilton, Kiel had up to six other jobs. “I think of it a little bit like cooking,” he says. “If I’m in the kitchen, I have something defrosting, there are things in the freezer, there are ingredients of things I haven’t even started to mix.”

While Miranda runs around on stage, Kail sits in the dark. “My job is often to distill all the information and figure out a couple things,” he says. For example, timing. “What you say is important but when you say [it] and how you say it are equally important.”

When it came to the line, “immigrants we get the job done,” for example, Kail and Miranda debated giving the line more time, or “asking for that moment,” as Kail puts it. But they worried about tempo and bringing too much attention to “Hi we’re liberal!”

So Kail let Miranda try his longer version on early audiences. It worked, and both men were pleased.

Another decision of Kail’s was how to direct the actor’s bodies. “From the neck down is then,” he says. “From the neck up is now. The hairstyle of the company is what everyone would wear on their night out.”

And, as the director describes, while the clothes stay in the 19th century, they move in a contemporary fashion. “I told Lin [the idea] and he was like ‘great try it,’” he says. “It’s important to prove over time that you are both trying to serve the same thing.”

It’s Kail’s style of rehearsal that he considers his greatest contribution to how things ought to be. “One of the things I’m really proud of is the process of making the shows I like to make,” he says. “The making of it is the thing.”

One of his rules? He doesn’t raise his voice. “I’m gonna ask [my actors] to do things they don’t wanna do,” he says.  “So I’m gonna be transparent with them. I’m in the business of really sensitive people with a lot of feelings. If I can make them feel safe I can make them feel their best.”

Another? He’ll admit when he doesn’t know. “I always feel a pressure to know the answer,” he says. “But an older friend of mine said, ‘If you give the actors space where they don’t know, you’re allowed to live there also’.”

And he cares about his actors. "Sometimes with coworkers or actors, you find yourself in an arranged marriage," he says. Having to fire an older actor was, as Kail describes, horrible. "I remember thinking if this ever gets easier then I should stop. If I ever get out of touch with my actor’s anxiety that the thing that they love to do is not enough to make this work, I should just stop.”

Kail also values the boundaries of his own skills.  “I surround myself with people who can do things that I can’t do,” he says,  comparing this idea to politics, a nod to his high school years at Sidwell Friends in DC. “If you’re president, you can surround yourself with people that say yes, or you can put yourself in a room with people who will challenge you.”

And just as Kail wants this diversity of experience in the studio, he aims for diversity in his production, determined to produce characters who wouldn’t normally be center stage. “Sometimes it’s about a bunch of people living at the top of Manhattan,” he says. “Sometimes it’s a family in Kansas City. We’re working against plays about a certain kind of status quo or a certain representation that we’ve seen before.”

“Theater is often not the cool kids table,” he says. “So there’s something about theater being part of the cultural conversation in the populous page. The fact that we’re off the Arts page, but can be a conversation about politics.”

And he isn’t leaving the table anytime soon.  “The reality is I make theater ‘cause I like making theater,” he says. “I’m not making theater as the minor leagues of Hollywood.”

In producing underrepresented characters, Kail hopes to bring the reluctant theater-goer to Broadway. “Theater is often put into a place where it is made exclusively by a group of people and consumed exclusively by a group of people,” he says. “I want to make the tent bigger and invite more people to the party.”

Perhaps it is his History major talking, but Kail sure does understand his work within the greater timeline of drama. “Lin saw Rent in ‘96,” he says. “12 years later there was In The Heights. 20 years later there was Hamilton.” His hope then, is that his plays bump someone else in a new direction.

As I sit surrounded by the Second Stage listserv, I find myself dreaming of where we'll all be in 20 years. Which, I may point out, is the first time I've felt any sort of hope in the Career Center. But then I stop myself. Or rather, Kail stops me. For, as he points out, our rehearsals are more important than our opening nights.

“Life isn’t about being there," he says. "The distance between now and that place is your life. So you should live your life. There’s nowhere where you arrive and it all lays out. It’s different changes, the scale of things might be different. But learn to hear it and get up and dust yourself off and keep going. Someone will say yes. And sometimes maybe is all you need."