When I picked up the phone for my interview with a Kennedy Center honoree and Tony- and Emmy Award–winning director, the person on the other end introduced himself as Thomas Kail. “Thomas?” I asked. “Who’s that? I always hear Tommy Kail.”

“I’m billed as Thomas Kail. A few people call me Thomas, but it’s mostly people who don’t know me,” Kail said. “When I first got to New York and started thinking about making anything, I thought Tommy Tune is the greatest Tommy director that exists with a one-syllable last name. So I thought I should be Thomas. And that’s a true story.”

Thomas Kail is a name that has since become synonymous with directing one of the biggest musicals on Broadway: Hamilton.

His creativity and talent have earned him top creative billing on so many other big musical projects. He directed the new revival of Sweeney Todd on Broadway starring Josh Groban and Annaleigh Ashford. For TV, he directed FX’s Fosse/Verdon and, most recently, Up Here, a musical comedy now streaming on Hulu. The story follows a young couple played by Mae Whitman and Carlos Valdes as they fall in love.

I got the behind-the-scenes scoop from Kail on how and why he develops his projects. And by the end of our 40-minute chat (that was supposed to be 30), I was allowed to call him Tommy.

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In the Heights

“I went to Wesleyan University and graduated in 1999. Lin-Manuel Miranda graduated three years later than me, so I didn’t know him. He was a freshman when I was a senior, and I didn’t talk to freshmen. When I graduated in 1999, I had a couple of friends who were still there. As a sophomore in 2000, Lin wrote an early version of In the Heights for the student-run theater. Two of my friends John Mahler and Neil Stewart saw it and called me to say that this kid — who used to take our lights from our productions, which is how I first heard of him — wrote a musical and it was really good. I said, ‘I’m the professional, I’ll be the judge of that.’ They sent me a demo CD that Lin made and a copy of the script in 2000. I heard it and thought that they were absolutely right. The music was the kind of music that I would listen to if I was buying a CD at the time. I was really fascinated by the idea of trying to use contemporary music to tell a contemporary story. Two years later when Lin graduated, I got in touch with him and told him my theater company wanted to start working on his show. That was in May of 2002. As we like to say, it began a conversation that has lasted 21 years and continues until about three hours ago when I just got off the phone with him. That’s how that one happened, which is quite different from most of the other ones.”

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Hamilton

“At that point, I was best friends with Lin. In 2009, Lin took his first vacation from Heights. On that trip, he was GChatting me, which is what the kids used to do when we were still kids. He mentioned that he was reading Ron Chernow’s Hamilton. I didn’t pay it any mind. When he got back, he was telling me about how he went online, and no one had written [a show] about it. So he decided to write an album that’s going to be a series of hip-hop songs, and a mixtape about [Hamilton’s] life. I told him that he should do that. You can tell when Lin’s antenna is up, and his antenna was up. It had been so much In the Heights for the previous six years that there hadn’t been a lot of writing outside of that. I could tell that there was something about this that was really speaking to him. He started working on the song for Aaron Burr, which he ended up performing at the White House. I asked him how it went, and he said it went pretty well. They happened to film it for HBO. Six months later, they put it out on the internet, and it started to ricochet around. I said, ‘It’s good. Where’s the next song?’ We had this benefit for Freestyle Love Supreme about a year later, in the middle of 2011. And I said, ‘Maybe this is a good chance to try another one.’ So we did it for the 96 people there. Lin did ‘My Shot’ with the group. Everybody was patting him on the back and telling him how wonderful he was. I realized this was my chance. I said to Lin, ‘You’ve written two songs in two and a half years. We’re going to be very old by the time you finish this. So why don’t we pick a date six months from now. I don’t care whether it’s Ars Nova or if it’s anywhere. Let’s just try to work on two songs a month and see what we can do.’ He said OK and called me the next day to say he had a venue and a date. Lincoln Center. January 11. Which is [Hamilton’s] birthday. Lin thought it was a sign.”

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Grease Live!

“I was at New York City Center [directing] Randy Newman’s Faust in the summer of 2013. I was developing Hamilton, but we were in the development process and we did not have a production schedule. I got a call from my agent telling me that they were about to do another live musical. He asked if I wanted to throw my hat in the ring. I said sure. I’ve had so many friends work on them before. They are really hard to do but they’ve had a thrilling time. Instead of imagining how I would do it, I thought, Why don’t I just go and see if someone would actually let me do it? So I had a meeting with Marc Platt. I told him I wanted to try to make sure that the experience of shooting this live is captured in the most full way. I wanted to do an opening using the first song as a way to let everybody know this is happening right now. I want to show the flats. I wanted to move around. I wanted to do it in a longer, sustained shot. I wanted to have an audience for this. I had this idea that if you’re walking on a tightrope, and everybody doesn’t fully comprehend how high that tightrope is, it loses some of its luster. So I said, ‘Let’s show that we’re really high up. Let’s show the size of the buildings that [the actors are] walking in between.’ That was basically the pitch that we brought to Fox. They said we could do it. Hamilton opened on Broadway in August 2015. I basically went right into rehearsal for Grease about two months later.”

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Fosse/Verdon

“There was a book that Sam Wasson had written. I had read it. Sam went to college with Lin. I didn’t know him, but I’d read some of his other stuff. I was in Lin’s dressing room in June of 2016, right before he was leaving Hamilton. He got an email while I was there, and it said Sam Wasson’s book was optioned by FX. Sam asked me if I wanted to produce it. He knew how much I loved the book. Sam Rockwell was a friend of mine, and I said Rockwell should play Bob Fosse and [Miranda] should play Roy Scheider. We sort of laughed about it. A couple of years later, I definitely asked him to play Roy Scheider. I then went to FX and spoke to them about it. I told them I talked to [Rockwell], who said he was interested in doing it before there was a script. So, we had a little momentum. I met Steven Levenson at a screening of La La Land. We sat next to each other and really clicked. We went out to lunch. I told him I was working on this project about Bob Fosse and Gwen Verdon and would he be interested? He said yes very quickly. That set us on our course.”

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Sweeney Todd

“Josh Groban called me about three and a half years ago, in 2019. Josh and I had been friends for about five or six years prior, and had never worked together. He told me he’s always wanted to play Sweeney Todd, and was wondering if I’d be interested in it. I said I would be very interested in that. We both said that if we do it, we wanted to do it at scale with that original form of orchestration. I said if I [directed it], I need to have a couple of people who I have made stuff with because this is so different. So I told him I’d like to call [Rent and Hamilton producer] Jeffrey Seller. If I’m doing something this big and this iconic, I need to have some of my real deep collaborators [working with me]. Jeffrey said he was interested. My next call was Alex Lacamoire, because I thought if I’m going to do this, I have to do this right, and we have to honor the music. I knew that those two would allow that to be possible. I arranged a meeting for all of us to talk, and we decided to join forces on it. Then the pandemic happened, and everything went away. In August of 2021, when [theater] started to come back, Josh called me and asked what I thought of starting up again. I said I’m still really keen to do it. I said I’d like to try to give myself an opportunity to be inside of the work in a reading process, because I’ve not had the benefit of that. That’s usually how I’m able to imagine the physical world for [a show] and not just study it academically. A reading is about 10 actors at music stands who rehearse for a week. At the end of the week, Jeffrey, the casting director, and [composer] Stephen [Sondheim] would come to see it with [Sondheim’s lawyer and friend] Rick Pappas. Hal [Prince] and I were close the last four or five years of his life, but I didn’t know Steve. Steve was obviously enormously close with Lin and a couple of my other really good friends. We were in touch through the estate and about Josh playing Sweeney. Steve was really an advocate for that. We wanted to invite our friend Annaleigh Ashford to do the reading, and Ruthie Ann Miles. Steve [was set to] come see it. That was scheduled for the 28th of November, and Steve died on the 26^th. Two days later, we were in this rehearsal room, which felt like being in a chapel with the music. We felt Steve’s absence deeply. But it also gave us a lot of insight and competence that we had a desire and an idea of how we wanted to do our version of Sweeney.”

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Up Here

“I was thinking about where we could make work since this was in the really early days of the pandemic. I thought about some people who I was either already working with or knew a little bit. I was friendly with [Kristen Anderson-Lopez and Robert Lopez], but did not work with them. I called them and asked if there was anything that they had that might work for a streaming series. One of the first things they said was this musical called Up Here. They’d been workshopping it 12 or 13 years before they went into production [for a version of the musical at] La Jolla Playhouse. When they told me about it, I agreed it could really work in this medium. They sent me the materials, and I really liked it. Then I said we should call Steven Levenson. Danielle Sanchez was someone I had worked with previously on a totally other project. We knew we wanted someone who really sat deeply in the world of half-hour television, had a real sensibility about TV, but also an appreciation of musical theater. We started working in the summer of 2020. It was 18 months on Zoom, we cast a lot of the roles on Zoom, and did a few of them in person. We shot it in June of 2021 at the same stages where they make Only Murders in the Building in Long Island City.”

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We Were the Lucky Ones

“I’m shooting something right now in Romania — We Were the Lucky Ones — which is not a musical. It is about a Jewish family’s escape from the Holocaust in 1939. It’s based on a novel, which is 99 percent true, written by Georgia Hunter. Georgia and I have been friends since 1999–2000. She married one of my best friends from growing up. I was very good friends with her as she wrote this book. I optioned the book into 2017. While I was making Fosse/Verdon, I called my friend Erica Lopez, who I directed a play with. She’s a really good playwright and an excellent TV writer. I asked her if she wanted to put together a pitch. The three of us worked on something. And then we went out to try to sell it in 2019. We went everywhere and everybody loved it. It was a great pitch. It was a story about a family that is trying to get together to have Passover dinner and it took them eight years. That’s really the center of the story. The pitch went out and didn’t sell. It wasn’t the right time. But there’s a reason why this book has sold 500,000 copies. It became a New York Times bestseller. And I said we’ll [try again] when it’s the right time. Six months into the pandemic, all of a sudden the world understood what the book was about. And Hulu bought it. I shot the first episode in December of this last year and we’re shooting right now. We’re shooting the last episode in about three weeks.”