The musical ‘A Strange Loop’ is boundary-pushing — even for Woolly Mammoth

When Michael R. Jackson became the first Black musical theater writer to win the Pulitzer Prize for drama in May 2020 for “A Strange Loop,” his metatheatrical mediation on race, sexuality and American artistry, that honor reverberated with aftershocks: a jolt of prestige, a cash prize and, more jarringly, a call from Tyler Perry.

As the self-referential story of a Broadway usher — like Jackson, Black and queer — who is working on a self-referential musical of his own when he gets an offer to ghostwrite Perry’s next gospel play, “A Strange Loop” does not look kindly on the Madea mastermind’s work. One example: During the scathing song “Tyler Perry Writes Real Life,” the protagonist refers to Perry’s productions as “simple-minded hack buffoonery.”

“He told me that he was going to beat my ass,” Jackson says of Perry with deadpan amusement. “But he congratulated me on the Pulitzer and the historical significance of that. It was a brief chat, and then he texted me later to show me that he had purchased the cast album and had listened to ‘Tyler Perry Writes Real Life.’

“He did not say what he thought of it or anything of that nature,” Jackson adds, noting that he never had any qualms with Perry the person — just his art. “But we touched base, and every once in a while I’ll text him.”

Catching Perry’s attention proved increasingly inevitable as the bawdy musical continued its buzzy ascent. By earning the Pulitzer on the heels of a 2019 production at the off-Broadway theater Playwrights Horizons, “A Strange Loop” became just the 10th musical to claim the prize and the first to do so without a Broadway run.

As Jackson, director Stephen Brackett and producer Barbara Whitman wait for the right Broadway theater to open its doors, “A Strange Loop” is keeping the momentum going with a production at an unlikely venue: D.C.’s Woolly Mammoth Theatre, a boundary-pushing home to intimate and experimental plays, but rarely musicals and never pre-Broadway engagements.

“I really am allergic to the idea of Woolly Mammoth being a place for out-of-town tryouts for Broadway musicals,” says Maria Manuela Goyanes, Woolly’s artistic director since 2018. “That’s not our purpose. Our purpose is to be a step with an artist to stoke and nurture their creative vision, provide a rigorous development in that and actually try to help them get to the kind of virtuosity that they really are aspiring to. In this case, it happens to be a musical that wants to go commercial, and that’s an amazing thing.”

The unlikely collaboration came about thanks to an appropriately cyclical development: Goyanes directed early readings of the show that became “A Strange Loop” in the mid-2000s, when Jackson was a graduate student in New York University’s musical theater program. After penning a personal monologue called “Why I Can’t Get Work” in 2002, Jackson fused that piece with several thematically similar songs he had written — including “Memory Song,” a soul-baring ballad that can still be heard as the show’s eleven o’clock number — to form that early iteration.

“To be honest, the piece is totally different from that time,” says Jackson, who wrote “A Strange Loop’s” book, music and lyrics. “But I don’t think I would have gotten to where I even got to without having spent that time really thinking about the piece very seriously with her.”

Jackson eventually pivoted from the originally conceived one-man show to a more traditionally staged musical, starring an ensemble of Black, queer performers, as he connected with Brackett, the director, to work on readings of the musical’s book and concert performances of its songs. Jackson then shelved “A Strange Loop” for several years before revisiting the show in 2015 during a residency at New York’s Musical Theatre Factory, culminating in a reading he recalls being “very messy but powerful.”

“It was a piece that I felt went to places that I had never seen on the stage before, and certainly not in the American musical theater,” Brackett says. “For a long time, we were like, ‘We’re never going to find anybody to produce this, right?’ It felt too much itself, and the voice felt too strong.”

Then came a November 2016 reading, days after the election of Donald Trump, before an audience including Whitman — a longtime Broadway producer whose musical credits include “Fun Home,” “Hedwig and the Angry Inch” and the Pulitzer-winning “Next to Normal.” The show’s rebellious spirit and idiosyncratic perspective struck a chord in that room, Whitman recalls, and she subsequently optioned the musical. But it wasn’t until “A Strange Loop’s” rapturous reception at Playwright Horizons that she came to fully comprehend the musical’s mainstream potential.

“When I first took on the show, my goal was to introduce Michael to the world and have them all say, ‘He’s amazing. What’s he going to write next?’ ” Whitman says. “Because the show is challenging, and it’s scary. But then to have the audience react the way they did, and the critics react to it and the Pulitzer, it feels like everyone is saying to us, ‘Oh no, we want to take this show forward.’ ”

“This piece is absolutely pushing so many boundaries,” Goyanes adds, “and I have been thinking that Michael just needed the world to catch up to him for this piece to be able to land.”

Woolly originally set its run of “A Strange Loop,” produced in association with Playwrights Horizons and Page 73 Productions, for September 2020 before delaying it because of the coronavirus pandemic. The result was more than two years passing between productions of the show, during which many of the topics it tackles — in particular, the theater community’s struggles with equity and inclusion — permeated the national discourse.

But even with such prescience, and the Pulitzer already in tow, Jackson isn’t done fine-tuning the show. After the Woolly run ends on Jan. 9, the hope is that “A Strange Loop” will find its way to Broadway sooner than later — thus completing the musical’s own, strange, two-decade-long loop.

“I certainly made no secret that I would be thrilled for a Broadway transfer,” Jackson says. “The show says it in the opening number: It’s a ‘big, Black and queer-ass American Broadway show.’ So I think it makes sense, and I hope to see that journey through.”

Originally posted in The Washington Post

By Thomas Floyd
December 9, 2021 at 10:00 a.m. EST