Two By Two: Broadway Bound with “We Are Freestyle Love Supreme” and “Best Worst Thing That Ever Could Have Happened”

Now that you’ve seen Hamilton (2020) at least five times on Disney+, odds are that you’re having a hankering to see more from wunderkind Lin-Manuel Miranda. Those songs are invariably catchy, full of this dexterous detail that boggles the mind and makes you secretly want to learn more about history (tell me more about Hercules Mulligan!). This is one of those musicals that hit the zeitgeist in a way that only the greatest form of theater has the advantage of achieving. Even if Miranda never makes another hit, he will go down as one of Broadway’s greatest lyricists solely for what he achieves in any of these major numbers.

In an alternate world, I would’ve encouraged you to use In the Heights (2021) as a chaser, finding out where this young, scrappy, and hungry kid got his start. I’d still argue that listening to the cast album breathes with such vibrant life that you’ll have trouble not calling Miranda a genius, someone who is capable of transcending the world of theater with something more modern and accessible. Few people can claim to have advanced the medium as significantly and successfully as he has.

Though if you want a great look into what Miranda did even before In the Heights, I would recommend checking out Hulu’s new documentary We Are Freestyle Love Supreme (2020). The story follows a group of friends who wanted to use freestyle rapping and singing in place of improv comedy. This was meant to reach audiences who weren’t attracted to the world of local theater, making them want to see what these crazy minds were going to get up to. In their early days, they would often raise interest for shows by performing at bus stops and street corners, comically drawing from their surroundings and making these stories strung together by rap bars.

It’s a novelty that should’ve gone away as quick as any beatboxing melody. It was goofy and meant more as an excuse to get together and have fun with your friends. In any other improv comedy group’s hands, there’s a good chance that this would be their fate. When it came to the group dubbed Freestyle Love Supreme (or FLS for short), it was just a starting point for these wildly different minds to come together and find ways to make 21st-century theater more evolved and interesting.

As Miranda mentions early on: life is not linear. People enter and exit with such frequency that it’s unclear when a story truly ends. That is how director Andrew Fried approached this documentary, which uses the familiar mix of talking heads and archival footage to show how FLS was a thing that never went away. Even as Miranda and cohort Christopher Jackson (better known to Hamilton fans as George Washington) went to the theater, they claim to have performed at least a few FLS shows annually.

It’s easy to see why. While improv footage often comes across as awkward without time or context, there is something amazing about being in the room where these shows happen. Whether it comes with watching Miranda and his baby-faced peers or in the 2019 Broadway revival, there is an electricity that can be understood. It isn’t just the way that they feed off of the audience, it’s how spontaneous the whole thing feels. If you had any doubt that Miranda could only write raps that took years to perfect, then you need to see him run with a theme. His ability to make complicated rhymes that reflected everything from conventional end-rhymes to consonant repetition is amazing. 

The same can be said for the supporting cast, who are each introduced in their own nonlinear form. While the archival footage often finds them onstage, they aren’t spotlighted equally at first. The original group is introduced simultaneously. Later members become more central later on. We watch them evolve, such as Arthur Lewis going from a keyboard player to a crucial part of the vocals. Everyone’s style is just different enough that their personal expression becomes complementary to everyone else. It’s a humble experience where everyone works together, even finding sound checks to be symbolic of their need to hear every word that each other says.

For the most part, Fried is a conventional documentary filmmaker that benefits from an endearing story. He began to film FLS in the early 2000s, finding them wandering around the street. There’s a vivacity to everything that makes you feel the power of their friendship. When Miranda, younger than he was now, gives interviews from his apartment there is this jarring feeling that he could ever have not been a massive success. There’s clearly so much energy there, and he seems grateful to his collaborators, including Thomas Kail who served as the director of both FLS and a key collaborator on In the Heights and Hamilton.

Where We Are Freestyle Love Supreme works as this origin story of some of Broadway’s modern greats, Best Worst Thing That Ever Could Have Happened (2016) is a story about a legend taking a different kind of risk. 

If you have even a passing admiration for Broadway, you should be able to recall Stephen Sondheim’s accomplishments. He is one of the most acclaimed composers of the late-20th century, producing hits like Company and Sweeney Todd: The Demon Barber of Fleet Street. By the time of the latter musical, he had a storied career that included ending the 1970s with some of his best work yet. You can argue that his best was still ahead of him. 

And yet, Merrily We Roll Along can rightfully be considered a misfire. It’s not his biggest flop (see: Anyone Can Whistle), but there is this frustrating sense that it never reached its full potential. The story focuses on Broadway-bound composers telling their story in reverse, starting with the cynical conclusion and slowly becoming more optimistic. I have never seen a recorded version of the show, but I love the soundtrack. It’s one of his most ambitious works. It’s so much so that the planned Richard Linklater adaptation with Ben Platt and Beanie Feldstein is going to take over a decade to film “properly.”

A big issue is that this is a high concept musical where there’s plenty of pressure on its young cast. How exactly do you convey being older when you’re still in your early 20s and have no personal instinct? There’s a handful of stories throughout Best Worst Thing that give insight into why the show failed. In some ways, it was the pressure to follow up Sweeney Todd with an even more harrowing achievement. Others involved typical theater mishaps.

For a musical that flopped, there is something to be said with its resonating power. Starting with a glance into the archival footage, the interviews slowly bring in talking heads that mattered to the making of the show. It’s all documented just as extensively as We Are Freestyle Love Supreme, where even rehearsal footage is presented. Once again, to see these young and optimistic eyes eager to work with Sondheim at the height of his powers is empowering. In some cases they weren’t even that well trained, making the push all the more rewarding.

It’s a story that once again feels like friends getting together to create this brilliant little project. Even if Sondheim as an interview subject feels secondary, he’s a prominent force, coming across as a mentor to his young cast. For Jason Alexander, Sondheim wrote “It’s a Hit” to force him to sing high and low notes. In an even greater story, the origin of Donna Marie Asbury’s main song is given an endearing origin story. At her birthday party, Sondheim invites them into her bedroom and performs this great song for them. Even from the rough sound recording, there is something endearing about the way it feels like a masterpiece being born.

In both documentary’s cases, there is something impressive about watching the young naivety being grappled with by the crew at an older age. As they come back together, time plays its cruel tricks of watching the unsure beginnings have their answers formed. In most cases, FLS and Merrily We Roll Along could fade into obscurity, especially as everyone aged and began working on other projects. 

We Are Freestyle Love Supreme inadvertently feels like an origin story of Miranda’s bigger career. Maybe that’s just a result of FLS existing in the back of everyone’s mind as he created the shows. Maybe it’s that Jackson and Kail would continue to collaborate, or how friend UTK missed out on playing Aaron Burr due to a battle with alcoholism. When we see Miranda and Kail wandering Broadway to find a poster of In the Heights hanging over The Richard Rodgers Theater, you can feel his thrill of touching greatness. To watch it fade into a banner for Hamilton comes across as beautiful.

And yet, FLS will always matter to Miranda. It fills him with so much life and purpose that arguably has kept him fresh and thrilling. He could do a million things, but no footage exists where he feels more alive than when he’s watching his friends drop rhymes. There’s also a fun story about crossword puzzles that shows how the spontaneity of living in the moment ultimately is a message that he’s giving us. We should follow our dreams and work hard to achieve them. After all, FLS got their start on the streets, asking strangers to give them a chance.

That is also the message that Best Worst Thing leaves us with. At the time the musical was such a flop that it notoriously lead Sondheim to retire, breaking up a relationship with collaborator George Furth for several decades. He would move into doing film composition and anything else, taking the criticism so harshly that he spent a near-decade doing anything but. The actors may have not had careers that immediately exploded, but their beginnings in Merrily We Roll Along gave them a work ethic, even gaining fans that would talk to them decades later about it. 

Unlike FLS, the crew remained largely dormant from working with each other until a reunion concert. With Sondheim and Furth in attendance, they witnessed the impact that the show had developed. They were able to look without painful bias, and the story of rekindling their partnership was a beautiful final note. Even if Sondheim hasn’t been as prolific since that concert, the story concludes eventually with a positive note, proving that every gamble does have some payoff. It sometimes just takes time.

In both cases, it’s incredible to note that some of Miranda and Sondheim’s best work was ahead of them. These projects were mere interludes, finding room to express a creative itch that they couldn’t elsewhere. They were innovative, maybe too ambitious, but they had fans that built over years, finding ways to use their trials and errors as learning curves. In the case of Miranda, In the Heights, Bring It On, and Hamilton was in his future For Sondheim, there was Sunday in the Park with George, Into the Woods, and Assassins. They were far from over, not allowing any concept of flukes to stop them from moving forward.

And, in an unrelated piece of synergy,
Lin-Manuel Miranda was in Merrily We Roll Along (2012)

I do encourage you to have some basis of understanding these figures in both cases. This is more of an addendum to great careers than an entry point. If you don’t have affection for Hamilton or Merrily We Roll Along, then something will be lost. With that said, there is something vital about these stories of artists growing and having moments that they learned from. They’re not always happy or sad stories, but in both cases, they inform how they endured the turmoil. They didn’t let one roadblock keep them from moving forward, and that is an incredible message to have. I personally would love to see a FLS set after watching this, if just because it feels like improv comedy elevated into a more interesting art form. Similarly, I want to see how Merrily We Roll Along is pieced together, making its abstract nature into something more profound.

Hopefully, the pandemic will end before Linklater’s version of this story gets released.