Hamilton ’s Thomas Kail Returns to His Improv Roots with Freestyle Love Supreme
Every once in a while, the hubris and pretension of undergraduate student theater leads to something great. Such was the case at Wesleyan University in 1998, when a junior named Thomas Kail got bitten by the theater bug after his friend Anthony Veneziale asked him to perform in an improv version of the German dramatist Heiner Müller’s inscrutable post-modernist play Hamletmachine that, with two African American Ophelias and two white Hamlets, aimed to dissect Race in America. “It was the most ‘Wesleyan’ thing of all time,” Kail says now with a laugh.
That production may not have set the world on fire, but it did lead to Kail and Veneziale’s starting a theater company together in New York after college, which led to a collaboration with another Wesleyan alum, Lin-Manuel Miranda, which resulted in Miranda’s Tony-winning musicals In the Heights and, of course, Hamilton, both of which Kail directed. It also set the stage for the now-legendary hip-hop improv show Freestyle Love Supreme, first performed in 2003 and eventually going on to feature a rotating cast including Veneziale, Miranda, and his future Hamilton costar Christopher Jackson, who dazzlingly—and hilariously—freestyled a series of songs and mini-musicals based on suggestions thrown out by the audience. After a five-week reunion run at New York’s Greenwich House Theater last winter, Freestyle Love Supreme comes to the Booth Theatre on Broadway this month under Kail’s direction. On the heels of co–executive producing and directing much of the sensational limited TV series Fosse/Verdon, Kail also has the new pop musical The Wrong Man opening at the Robert W. Wilson MCC Theater Space this month and is a producer, along with J. J. Abrams, of the English mentalist Derren Brown’s astonishing one-man show Secret, which just opened on Broadway. A director at the height of his artistic and commercial powers, Kail is as excited about returning to his roots with Freestyle as he is about mounting new work.
“I don’t know if there’s a show I’ve ever done that makes the back of my head hurt—in the best sense—the way that Freestyle does,” he says. “We’ve all been in each other’s lives, and in each other’s faces, for a long time, and there’s just something about the energy of it that still generates some of the purest expressions of joy that I’ve ever been around.”
With an unruly thatch of curly, dark-brown hair, handsome features, and a permanently wry mien, the compactly built 42-year-old director cuts a boyish figure. He is ebullient and fast-talking, though at the same time he exudes an aura of calm self-assurance and quiet authority. This may be why members of the extended Freestyle Love Supreme crew, all roughly his contemporaries, refer to him as “Dad.” (Though Kail is not yet an actual father himself, he says that, outside the theater, his favorite thing to do is be uncle to his five nieces and nephews, three of whom are in New York City, where he lives.) Growing up in Alexandria, Virginia, Kail didn’t seem destined for a life in the theater. A soccer-and baseball-playing jock at Sidwell Friends School, he headed to college with dreams of becoming a sportscaster. Veneziale, a sophomore and leading light of the campus improv scene, met Kail on his first day of school, bonding with him over their shared love of ’90s hip-hop, which they tested by throwing out lines from the likes of A Tribe Called Quest and Digable Planets for the other to finish. They also shared a gift for freestyling—improvisational rapping, with the flavor of a jazz solo. Kail traces the genesis of Freestyle Love Supreme to a cross-country car trip he and Veneziale took, during which, to stay awake, they put on a CD of a sped-up version of Daft Punk’s “Around the World,” hit repeat, and freestyled over the beat for hours. “I said, ‘Tell me all of your stories,’ ” Veneziale recalls. “And we rapped nonstop until we made it to Des Moines.” Kail adds, “When you get to that place, the filter comes off, and anything goes.”
That spirit of no-holds-barred experimentation animated Back House Productions, the theater company that Kail, Veneziale, and two friends started in New York City after graduation, housed in the basement of the late, lamented Drama Book Shop on West 40th Street. This was where Kail and Miranda first met in 2002—and the chemistry was instantaneous. Two years earlier, Kail had been given the script and a demo CD for an early version of In the Heights, written during Miranda’s sophomore year at Wesleyan. After they bonded over a mutual passion for Biggie Smalls and Big Pun, Kail gave Miranda some thoughts about his nascent musical. “I had all this ambition, some talent, and not much of a clue how to get there,” Miranda recalls. “He saw the path.”
During the early days of working on In the Heights, Miranda and Veneziale would blow off steam by freestyling together, and Veneziale finally suggested that they try it in front of an audience. An improv veteran, Veneziale was comfortable being onstage without a net from the beginning. (“After a while, you start dreaming in improv and rhymes—it’s like speaking another language,” he says.) Miranda, on the other hand, was “petrified,” but, he explains, “you learn to just trust your gut, and you jump out of the plane, and you build the parachute on the way down.”
Soon Miranda and Veneziale filled out their ranks with other freestylers and asked Kail to take a look at what they were doing to help them pull it together. “Tommy understood how to weave our short-form improv games into a long-form experience,” Veneziale says. “He turned it into a show.”
After years of performing together at various theaters and festivals, the Freestyle Love Supreme crew has the tight-knit precision of the Guarneri String Quartet and the loosey-goosey virtuosity of the Harlem Globe-trotters. The current lineup consists of Veneziale, Utkarsh Ambudkar, Andrew Bancroft, the beatbox wiz Chris Sullivan (who goes by Shockwave), and, providing musical backup, Arthur Lewis and Bill Sherman—plus drop-ins by Miranda and others. Since each show is different, it’s hard to call out individual moments or performances, but by the time they reenact a day in the life of one of the audience members and then rewind to play it out with a happier ending—along the way calling back words and jokes and moments from throughout the collectively experienced show—you will realize that you have seen something not just hilarious but profound. Living completely in the moment, it turns out, can elevate the mundane into something almost magical.
It’s the same kind of magic that should feel familiar to fans of Miranda and Kail’s larger-scale and better-known ventures. “If you go to see Freestyle, you can see the DNA of In the Heights and Hamilton,” Kail says.
In the years since the once-in-a-generation phenomenon of Hamilton, Kail has been focusing on directing plays at the Public Theater (Tiny Beautiful Things; Kings) and high-profile TV projects (Grease: Live; Fosse/Verdon). It makes sense that, with his first musical on the New York stage since then, Kail would choose to direct something on a more intimate scale. The Wrong Man is based on a rock-song cycle by Ross Golan about a drifter framed for murder. Golan is a gifted and prolific—not to mention multiplatinum—musical shape-shifter who has written songs for, among others, Ariana Grande, Justin Bieber, Nicki Minaj, Charli XCX, and Maroon 5. Though it has also been produced as a concept album and an animated film, The Wrong Man started as a collection of songs that Golan would perform for small gatherings in friends’ living rooms and barns, quickly attaining a kind of cult status. When Kail heard Golan perform the hauntingly melodic songs—part emo, part folk, part hip-hop—he immediately thought, he recalls, “Holy shit—this guy can write a song and tell a story! I knew that I wanted to work on his first musical.”
Kail immediately brought in his In the Heights and Hamilton cohort, the brilliant Alex Lacamoire, to do the musical arrangements and tapped Joshua Henry—last seen on Broadway giving a powerhouse performance in Carousel—to play Duran, the man unjustly accused of murder. He has since rounded out the cast with Ciara Renée and Hamilton alum Ryan Vasquez, who will be joined by six musicians onstage, and brought in Travis Wall to do the minimalist choreography. With the audience on three sides and nothing but a couple of benches onstage, The Wrong Man is a far cry from some of this season’s more razzle-dazzle musical offerings, such as Moulin Rouge! and Tina: The Tina Turner Musical. “It felt like an opportunity to work on a different kind of canvas,” Kail says. “I loved the scale and the focus of it.”
Intimate or not, The Wrong Man has been gathering the kind of buzz that heralds a cultural moment, and there are already rumors of a Broadway transfer. If it does move to Broadway, it will be joining Derren Brown: Secret, which Kail first saw during its off-Broadway run at the Atlantic Theater Company two years ago. A huge stage and TV star in England, Brown has remained relatively unknown here. Kail first discovered him several years ago, when a fellow magic nerd urged him to watch some of his mind-bending mentalism on YouTube (full disclosure: That nerd was me), and his desire to produce the show on Broadway is based on nothing more than his excitement to share the experience with as many people as possible. “I don’t think there’s enough wonder—everything is known,” Kail says. “We can take a device from our pocket and it can tell us anything we want. I don’t go to see Derren to try to solve how he does what he does. I go to be taken away.”
Among Kail’s strengths as a director, his greatest, Miranda says, may be that “he always makes sure that we bet on ourselves.” Clearly, Kail’s bets have been paying off (and, looking ahead, he has optioned his friend Georgia Hunter’s best-selling Holocaust novel We Were the Lucky Ones as a limited TV series). “I’m a populist—I want to make things that lots of people can have access to,” Kail says. “But I don’t ever think about what’s going to sell. I have a good instinct about what I think deserves to be seen, so—whether it’s a play for a hundred people or a TV show for potentially millions—all I can do is trust that instinct, do my homework, and let the chips fall where they may.”
Lin-Manuel Miranda and the Freestyle Love Supreme crew want you to join them at their opening night on Broadway. With your support of $10 to Planned Parenthood Action Fund and International Planned Parenthood Federation/Western Hemisphere Region, you can enter to win two VIP tickets to the show. Click the link for more details and a chance to win here.
Originally Appeared on Vogue
