Thomas Kail '99 explained how he didn't throw away his shot.


In an event co-sponsored by University Relations and the Wesleyan Career Center, Thomas Kail ’99 stopped by his old stomping grounds to give a talk in 41 Wyllys. Kail, an accomplished director of theater and television, has recently gained notoriety for helming “Hamilton,” the biggest Broadway show in recent memory. Pam Tatge ’84, Director of the CFA and moderator of the event, began the talk by personally thanking him for the show. But for the hour-long talk, Kail largely looked to his roots, talking about his time at the University and his career immediately following; also, about being fired from The Ampersand.

“I only took one theater class,” he admitted early on. “It never occurred to me that one could have a life in the theater.”

The first time he worked on a production was the fall of his junior year, when a friend asked him to help out.

“Second Stage and student theater here was absolutely essential in my development and my access to theater,” he said. “If you wrote a play or picked a play off the shelf, you could go and fill out an application, and try to express yourself and then sit and talk with them and then they’d give you a hundred bucks and they’d say you’re in the WestCo Café on these dates. And what I didn’t know at the time is that that’s one of the core values of a producer.”

Kail majored in history, but took many classes in American literature after spending a semester at Dartmouth.

“As I’ve always said about Wesleyan, there’s always a lot of doors,” Kail said. “Some of them ajar, many of them closed, none of them locked. But if you don’t get off your ass and check, people aren’t gonna spoon-feed you, people aren’t gonna lead you by the hand, and that’s basically what life is like.”

Kail went on to encourage students to take advantage of Wesleyan’s resources to create things while they could, because those resources become much sparser after graduation.

He then talked about being rejected from the only job he applied to after college, assistant dramaturge at the Arena in Virginia.

“I thought, okay, I’m gonna get any job in the theater I can, and come back next year,” he said.

He repeatedly touched on the fact that he felt he was “behind” and had to catch up on theater knowledge after graduation. Kail eventually became an assistant stage manager for a small theater company in New Jersey.

“The job paid $100 a week before taxes, and even in 1999, not a lot of money, guys,” he said. “I had this meeting, and as I was walking out, he asked ‘have you ever driven a 15-passenger van?’ and I said, ‘Have I?’ which is technically not a lie.”

Kail quickly became promoted with the company, to the point where he realized he had to turn down a job offer from the Arena.

“You are going to start somewhere where you’re not doing what you might think you are qualified to do,” he said. “You have to do the thing in front of you well. If you don’t do that, the other stuff doesn’t matter.”

For the next year he would alternate between attending creative meetings, driving the van, and working with his Wesleyan friends to create an independent theater company.

Tatge then turned the topic towards collaboration, citing that the Washington Post called Kail’s partnership with Lin-Manuel Miranda ’02 the most important in theater history. Kail didn’t miss a beat in countering, “well, you’ve got to sell papers somehow.”

“I try to surround myself with people who can do things I couldn’t do…you can surround yourself with people who say yes, or, and I’m not saying it’s like, straight up  ‘Team of Rivals,’ or you can surround yourself in a room with people who are doing the things you can’t do, that are asking questions you wouldn’t ask…” he said. “I also am not interested in people whose [sic], I’ll put it this way: There are a lot of towns of people in the world, and you can find a lot towns of people who are kind and good and decent, and I refuse to work with people who are not. And the beauty of having my own company early on, while I wasn’t getting paid to do anything for those first five years…I just found that if I was someone who was able to control who was in the room, quality of person was more important to me than time. Every time. And if you continue to put yourself in situations where you are not the most experienced, and you’re not necessarily the most knowledgeable, then there’s a chance for growth.”

Questions quickly turned to the Broadway show “Hamilton” and Lin-Manuel Miranda.

“I think one of the things that Lin does that’s really remarkable is Lin will bring in something half-baked and unbaked or just a recipe and share it with us because he knows our interest isn’t to serve it; it’s to understand what the impulse of that thing is,” Kail said.

Kail also turned to Miranda’s collaboration for “In the Heights.” Current Visiting Professor Quiara Alegría Hudes, the writer of the book off of which the show is based, sat in the front row.

“The way that I’ve described my relationship with Quiara or with Lin is, I didn’t meet Lin at Wesleyan, I came up here and saw his senior project, I talked to him very briefly there, and then we invited him to this little theater company that we had started,” Kail said. “And I sat down in June of 2002 and I just never stopped talking to him. And that’s the way I think about it. It’s a 13-year conversation. Sometimes its three times a day, sometimes it’s every other day, when we’re working together it’s 50 times a day, but we never stop communicating.”

When asked if he wished he had spent his time at the University differently, Kail said yes, but stressed that there must be a balance. 

“If you don’t have a life outside the theater, you can’t have a life inside the theater,” he said. “And that’s the same work balance no matter what you do. You have to go and fill yourself up.”

He then stressed finding the balance between consuming art and finding your humanity.

Another student asked how Kail approaches directing shows that predominantly offer roles to actors of color.

“I tend to try to work on shows that are gonna have people come see the show that don’t think theater is for them,” he said. “So what that often attracts me to are stories about people that are not often put on center stage, but they’re way over in the corner or they’re in the background…I’m not in the business of answers, I’m in the business of asking questions.” 

For each question, Kail sought to offer universal advice in the answer, such as when he was asked how he dealt with constant reject.

“Well the reality is, life is basically a series of people saying no to you,” he said. “Find the people who say yes. Empower yourself so that your yes also means something…. People don’t often talk about the no’s, but Lin and I knocked on a lot of doors for ‘Heights’ and heard a lot of no’s. And by the way, when Lin and I were talking early on about ‘Hamilton,’ after ‘Heights’ and the other stuff we’d done, we got a lot of strange looks also. So it doesn’t just go away. There’s no Shangri-La. If you’re not trying to get to some mythical place where the unicorn says, ‘It’s all yours!’ I think it alleviates some of the burden for yourself…the distance from now until that place is your life. The word ‘no’ will be shouted at you all the time, so just learn how to hear it, and get up, dust yourself off, and keep going. Somebody will say ‘yes.’ And somebody will say maybe, and sometimes maybe’s all you need. Ooh, hashtag that.”

When asked about how he collaborates, Kail asked for Hudes to respond instead.

“Meetings with Tommy for ‘In the Heights’ would sometimes happen in the playground at Central Park, depending on the weather,” Hudes said. “[What] would sometimes happen in my living room and Tommy would be lying on his back on the floor and Lin would be huddled over his laptop and I might be pacing or biting my fingernails. And there would be a topic at hand, like, ‘Is the opening number as best it can be?’ And that gets announced by whoever feels like they have an idea of where there is room to grow in the show. Sometimes Lin would send an email at two in the morning saying, ‘I had this idea! What if the Piragua Guy has a song?’ And it was like, ‘That wasn’t the topic at hand, Lin. The topic at hand was, how do we solve this problem in act two?’ [laughter]. Tommy is particularly good at following the ‘what if?’ If Lin had an idea on a new lyric or how Nina and Benny might be useful at that moment, Tommy could think very quickly about ramifications about the domino cascade after that. So Tommy would say, ‘Oh right, because there’s that moment an hour later where that happens so that feels like a really good stepping stone’ or he would say, ‘But what about that thing in act two where this happened? That feels like a contradictory impulse.’”

“And again, my job when I’m working on a play is, what is the author’s intent?” Kail added.

For Kail, the event was a chance to come back to Wesleyan to share what he had learned—to emphasize the balance between trusting your own drive, and finding that drive in others. With that in mind, it’s hard not to see that story reflected in “Hamilton.”

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