‘Hamilton’ Director Thomas Kail Talks Helming Improvised Musical ‘Freestyle Love Supreme’

Justin Barber

One of the joys of live theater is that it’s ephemeral — a show is never the same from night to night. But “Freestyle Love Supreme” has taken that up a notch, presenting an entirely improvised hip-hop musical revue created live on the spot. The recipient of a Special Tony Award in 2021, the show has played all over the world since its inception in 2004 and now finds itself in the Los Angeles area at the Pasadena Playhouse through Aug. 7.

Originally conceived by Anthony Veneziale and created by Veneziale, Lin-Manuel Miranda and Thomas Kail, who also directs, the shows roots took place during rehearsal breaks for another Tony-winning musical, Miranda’s “In the Heights.” Under Kail’s guidance, a structure began to take place, with an emcee moving the show along and certain freestyle games becoming part of the repertoire. But absolutely anything can happen: on opening night in Pasadena, Veneziale delivered an emotional rap while revealing he was leaving the show to spend more time with his family.

A Tony winner for his direction of “Hamilton,” Kail is a frequent collaborator with Miranda, having also directed “In the Heights.” He is also a sought-after screen director, having served as director and executive producer on “Grease: Live” and the series “Fosse/Verdon.” Variety recently spoke to Kail about the long journey of the show from backstage to center stage and what’s up next.

You’ve been playing all over the world for years now — what has it been like to see the show in so many places? And how has it evolved?

It’s interesting to me that when we were first putting on the show, it was in basements and music clubs, and then comedy clubs. No one really knew where to put us. We weren’t a straight-up comedy show or a straight-up music show. And theaters in the mid-2000s weren’t all that open to programming what the show is now. So it fascinates me that 15, 17 years later, we can be on a season roster with shows that have been in the canon.

But even in the beginning, I was struck by how the language of music and the language of hip-hop was connected. And now, there is so much more openness to how we define what theater is than there was 15 years ago. I feel like audiences are coming in open-hearted and ready to have whatever experience there is.

I assume “Hamilton” was a big part of familiarizing and helping audiences appreciate something like this?

I might not be the best person to answer that question. (Laughs.) But the fact that we are playing this tour in places like the Pasadena Playhouse or Seattle Rep, as well as the Kennedy Center – it’s both in regional institutional theaters and touring houses. So I think there’s something there that reflects just the way that musicals have evolved over the last five to 10 years since “In the Heights,” which closed on Broadway in 2011.

Do you find the show plays differently in other counties and cities, or has the response been pretty universal?

I wonder if the answer can be both. Because the show’s power is that it feels like it’s just for you and it’s just for that night. And it truly is. If you see the show in Philly, it’s going to feel different, because of the energy of everybody that woke up in the Philadelphia area and descended on the show that day. I’ve now seen the show hundreds and hundreds of times in so many different places. And I can say that whatever that specificity of the moment is, it is able to reach and transcend to no matter where you are.
Kaila Mullady, Jay C. Ellis, Andrew Bancroft, Morgan Reilly in “Freestyle Love Supreme.” Joan Marcus

The show began as a fun exercise and has now become its own beast. Do you think that’s sometimes where the best ideas come from?

What I love about the show, and especially the way it has grown and evolved over the last three years, is that it went from a show with seven or eight members to a show with 30 members. I’m really interested in community building, both with audiences, and also with people that I’ve gotten to meet, who have this very specific skill. And so the fact that the show can go on tour, the fact that the show can play on Broadway, means that we have the chance to expand the group experience. And to me, that’s the most satisfying thing about its longevity — that new people can find their way into it, just as new people find their way into the seats to watch it.

So I have to ask the obvious question: how do you direct an improvised musical?

It is the question that I get asked the most. I’m really conscious of the fact that directing and coaching have a lot in common. And this feels like coaching a team probably more than any other show that I’ve worked on, because you can run plays and you can have a system but you never know what’s going to happen. You’re not playing against the audience the way you would an opponent, but you are playing together as a team. And you don’t know what energy will be brought into the room, what suggestion you’ll get, what story you’ll get. So you’re trying to create a framework, but within that framework, there has to be complete freedom. I watch the show in the same way that I watch other shows, I just talked about the text slightly differently.

At opening night at Pasadena Playhouse, Anthony revealed he was leaving the show. Did you know he was going to do that?

Not at all. That came up during a part of our show called “True,” where you have to say the thing you’re feeling with no filter, and that’s what he was feeling that night. I think it’s a testament to his openness and vulnerability — but also to the power of the show.

As for him leaving the show — I’m not totally up on all the Marvel lore — but to me it’s like the Avengers. You never really leave; you’re always going to be an Avenger. Anthony is in many ways the author of the show and he will always have a huge role, whether he’s on stage or not. And I feel like we’ll find some fun ways for him to keep having an impact.

You work across so many genres and mediums; what’s up next for you that you can talk about?

I can tell you I just came from the set of a TV show for Hulu I’m doing called “Up Here” – it’s a new musical written for television. Kristen and Bobby Lopez are doing the music and Steven Levinson, who wrote “Dear Evan Hansen,” is a writer along with Danielle Sanchez-Witzel, a wonderful TV writer. I’ve never done an original musical for the screen, it’s always been something that existed, so it feels like an exciting hill to climb.

I’m also in the throes of a limited series I’m producing and directing for Hulu called “We Were the Lucky Ones,” based on the book by my dear friend Georgia Hunter, about a family who escaped from Poland in 1939. The wonderful Erica Lipez is our head writer and that’s starring Joey King.

Does Lin get jealous when you moonlight with other artists like the Lopezes?

(Laughs) Lin is the first person to buy a ticket if I do anything else. And I feel the same way. It’s funny because I was FaceTiming with him a couple days ago and I was running around to all these places while he said he was able to relax for a moment. But last year, I remember feeling I was relaxing when he was having 43 movies coming out. I honestly feel so lucky to get to work with and know the people I do because I would watch all of their stuff anyway.

“Freestyle Love Supreme” runs at the Pasadena Playhouse through Aug. 7. For tickets and information visit

Comments / 0

Comments / 0