We Are Freestyle Love Supreme Reveals the Origins of Lin-Manuel Miranda, Thomas Kail, and the Hip-Hop Improv Group That Started It All | Playbill

Interview We Are Freestyle Love Supreme Reveals the Origins of Lin-Manuel Miranda, Thomas Kail, and the Hip-Hop Improv Group That Started It All Hamilton and Freestyle Love Supreme director Kail and filmmaker Andrew Fried discuss the history of the documentary and its humble beginnings featuring Miranda, Christopher Jackson, and more.

Those who saw Freestyle Love Supreme circa the early oughts—when it was more akin to a UCB show or “friends doing skits” than the full-scale neon-lit Broadway production that most recently played the Booth Theatre this past fall—are part of a club. It’s the club that was in on the ground floor, who watched Lin-Manuel Miranda and Anthony Veneziale in a show shaped by Thomas Kail long before they were Lin and Anthony and Tommy. “Because it was so underground for so long, it created such a sense of deep connection with the audience. The audience would never want to go home after the show. They would just stick around,” says Kail, who directed the show in its infancy through its Broadway run. If you were in that club, you wore that membership as a badge of honor: “There was a real sense of ownership like, ‘We know something other people don't know,’” Kail continues. “And that's something that I think really kind of stayed with the show.”

Now, the club expands with the July 17 release of the documentary We Are Freestyle Love Supreme on Hulu. Directed by Andrew Fried, the film chronicles a 15-year history of the hip-hop improv group and, more profoundly, an intimacy of friendship we don’t often see from a group of men.

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Thomas Kail in We Are Freestyle Love Supreme Courtesy of Hulu

While theatregoers wait for Freestyle Love Supreme to come back in some form (“Our hope is to take the show out on the road to go to places we've never gone and to continue to grow the group,” says Kail), Fried and Kail let us in on the origins of the little improv troupe that could and the documentary they didn’t even realize they were making.

Andrew, when was the first time you saw Freestyle Love Supreme and what was it about them that you thought to yourself, “There's a story here”?
Andrew Fried: My friend Brett urged me to see a show called Freestyle Love Supreme in the summer of 2005. He just kept telling me about it: “You should see the show. You should see the show.” Finally I got an email from him that said, “Tomorrow's the last show. So see it or don't, but it will be your loss if you don't.” I had been an aspiring actor. I had done stand-up comedy. I had done improv. I had given that up by the time I saw Freestyle Love Supreme the first time, but I remember leaving that show almost jealous. I remember just being so jealous of these guys who were so talented. They were so funny. They were so smart, and it seemed to be effortless for them. I could never do any of the things that they were doing. Never mind all of them at once.
Thomas Kail: Andrew reached out to us. He basically said, “I watched your show. And part of me was really mad and jealous that I can't do that. And the other part of me said, "I think I need to spend time documenting you.” And so we went to go meet with him the day we went to Edinburgh; Anthony and I had our suitcases at our feet and then we're going straight to the airport.
Fried: They came in and they had suitcases with them. I remember thinking, “Are they ventriloquists also?” They said, “We're on our way to the airport. We're leaving for Scotland for a month to perform at the Edinburgh Fringe Festival.”
Kail: And Andrew, who we'd never met, said, “I want to come and spend some time with you.” And we said, “Give us a couple of days to get set up.”

Simple as that?
Fried: I went into my boss John Cayman's office and I said, “I've met this group of performers. They're more talented than anyone I've ever encountered. I want to try and do a television show with them, but they just left New York for a month. If I don't film them now, by the time they get back, it will be too late.” I really was convinced that Edinburgh was a huge bit of exposure for them. And by the time they were done with that one-month run, everybody in the world would know what I discovered at Ars Nova, and it would be too late.

John wrote me a $5,000 check and his advice to me at the time was: “You should go and film the footage and get whatever you get, but try to build a relationship with them. That is the value of this trip.”

Kail: Andrew came and stayed with us, and he was filming all of that just to maybe see if there was a short trailer we could put together to see if there's any interest in the group. No one knew who any of us were. I mean we didn't know who we were.

So the intention was to create a pilot so the world would know who they are?
Fried: We edited 60 different versions of that footage from Scotland. And then the subsequent footage that we shot with the group in New York. I was so convinced that there was a TV show to be had, like almost like the initial conceit of Seinfeld where—because improv is such an unfiltered medium—you'd see them do something during the day and then it would end up in the show at night.

Bryant Fisher and Andrew Fried in We Are Freestyle Love Supreme Courtesy of Hulu

So how did it turn into the documentary instead?
Fried: I knew I had a box of tapes. I knew I had a hard drive in my storage unit with some pretty special material on it. I knew I had footage of Lin-Manuel Miranda before anybody knew his name, rapping in the streets of Edinburgh, Scotland, and rapping in the streets of New York City. I remember the day that we stood outside the supermarket in the West Village and Lin grabbed things from people's shopping bags and started freestyling about orange juice. Like I remember that day, and I assumed that somebody would find me. I just thought at some point a documentarian or a biographer or somebody would say, “Are you the guy with all the old footage of Lin and Chris and Bill and Shockwave?” I really didn't imagine that it would be me.

We had this running joke through the years where we would always say to each other, “Are we rolling on this?” When Tommy was telling me about this run that they were going to do downtown in January 2019, I think I half expected him to just make that joke and say, “Are we rolling on this?” But instead he looked at me and he said, “Should we finish our film?” That was the first time it was a film.

Watching the film, I didn’t realize, Tommy, that you and Lin hadn’t actually met at Wesleyan. That the group didn’t officially form in undergrad. How did you come into the fold of freestyling? Were you always in the director role?
Kail: There's a picture in the documentary of me wearing a terrible bandana around my neck and glasses. It’s me and Anthony and a couple of our friends in that show, which was an improvised version of Hamletmachine, which we did my junior year, the first time I'd ever worked in the theatre. Anthony asked me to be his assistant director. And in that show, as the audience came in, we would all freestyle on stage, and it was just like a thing we did to kind of get loose. I would participate in that. No one in the world should ever watch me freestyle or perform. [Later], when Anthony and Lin said they have this idea, I went to see the show, and I think it was like 45 minutes with the saxophones and a lot of alcohol. And I said, “I think there's a structure that we can apply to this and take a lot of that spirit.” [Today] the container is the same, but what we fill it with, it's completely different, especially now that we have five, 10, 15 years of being together.

What are you trying to harness from them and make sure we see as an audience?
Kail: It is completely the same as if I'm directing something with text. I try to create the safest possible environment for people to express themselves. That's always my job. And the director's job effectively is to make sure that everyone in the room is on the same page and telling the same story in the same way. So in terms of how you try to create environment and shape a form that allows people to interact without the benefit of the same text is a little bit of a different challenge because we don't spend time talking about the text, but we still do talk about character choices. It's just variable from night to night depending on who's leading a particular game. You still have to set up the wants and the needs of a character. You have to try to establish the given circumstances.

Anthony Veneziale, Utkarsh Ambudkar, and Kurt Crowley in We Are Freestyle Love Supreme Courtesy of Hulu

Tell me a little bit more about this idea of developing a character because until you said that my assumption is that these performers walk on stage as themselves.
Kail: It’s not like, “Oh, Lin-Man needs to be this or that or UTK is this or that.” But if you watch the show enough, you'll see that Chris [Jackson] is going to bring a certain kind of gravitas and weight. Anthony is going to be the mischievous interlocutor, who is guiding us through it. UTK is definitely the kid who was always getting in trouble. Now within certain games, like a “Second Chance” or “A Day in the Life,” which are more narrative and story-based situations, then there's a lot about character that you can talk about.

Like Mic 1, the Two-touch track that he created, is the person that hosts the show, moving the ball down the field. Jelly donut has done that. Wayne Brady has done that. Mic 2, which is usually the person that's the rhymiest, you know, a UTK does that, a Lin does that, Andrew Bancroft does that usually. Mic 3 is someone that's a little more like sort of traditional vocal, like Chris Jackson, the James Iglehart, or Aneesa [Folds].

READ: Meet the Cast of Broadway’s Freestyle Love Supreme

There was that line where Tommy, you say, “We shouldn't be able to do this,” as in all logic says we shouldn't still 15 years later be doing this. Why not?
Kail: There's been so much joy and so much life with this group, and we've all stayed in each other's lives and just the fact that we're all still here, just in the most basic sense, really struck me.
Fried: It’s a movie about collaboration, and it's a story about friendship over time. The purity and the depth of that friendship I think is something important to see.
Kail: I remember doing that interview [with that line]. It felt really important to talk about what it means to be in a chosen family. There's something about the show for all of us, and obviously the film is full of it. Talking about why we continue to go back to it …that feeling of being unencumbered and to feel that free. And you feel that free when you feel that safe, and you feel that safe when you feel that loved.

We Are Freestyle Love Supreme premieres July 17 on Hulu. The film is produced by Kail, Miranda, Jenny and Jon Steingart, Jill Furman, Sarina Roma, Fried, and Endeavor Content.

This piece combines interviews with Kail and Fried and has been edited and condensed for clarity.

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