A Strange 20-Year Loop to Broadway

June 05, 2024

From the porn studio to the Tony Awards.

The cast and crew of A Strange Loop in collage at the Lyceum Theatre. Photo: Pelle Cass

The cast and crew of A Strange Loop in collage at the Lyceum Theatre.

The course of musical theater never did run smooth. Michael R. Jackson should know. The playwright first started working on his Pulitzer-winning show, A Strange Loop, when he was 21 years old. He’s 41 now. Two decades and 11 Tony nominations for it later — the most this year — he’s fairly Zen about how long it took Broadway to notice his work. “It’s worth it to take your time,” Jackson says, wearing a T-shirt that quotes the signature lyric, “Big, Black, and queer-ass American Broadway show.”

A Strange Loop's Cast and Crew

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Michael R. Jackson, creator
Stephen Brackett, director
Rona Siddiqui, music director
Barbara Whitman, lead producer
Jaquel Spivey, actor
John-Andrew Morrison, actor
James Jackson, Jr., actor
Jason Veasey, actor
L Morgan Lee, actor
John-Michael Lyles, actor
Antwayn Hopper, actor
Arnulfo Maldonado, set designer
Montana Levi Blanco, costume designer
Charlie Rosen, orchestrations
Michael Walkup, producer
Kent Nicholson, producer
Shakina Nayfack, show developer
Lilly Claar, publicist
Cherie B. Tay, stage manager
Jen Schriever, lighting designer (not pictured)
Drew Levy, sound designer (not pictured)
Raja Feather Kelly, choreographer (not pictured)

Indeed, A Strange Loop is all of those things — that’s precisely why Jackson never thought it would be produced. It’s a story about a Black gay man named Usher who is trying to write a musical, also called A Strange Loop, about a Black gay man trying to write a musical. Usher is surrounded by a Greek chorus of his obnoxious, self-hating thoughts, which keep insisting that he sell out and write a play for Tyler Perry. The musical is partly inspired by Jackson’s own life — Usher works as an usher at The Lion King, just as Jackson had. And he and his character share a contentious relationship with Perry’s work. Through its lengthy development process, A Strange Loop underwent countless loop the loops of revisions, workshops, and more revisions. Here, its key players detail the dizzying path to production — and the sense of déjà vu that drove its success.

2002

The bungalow that started it all.

Michael R. Jackson graduates from New York University with a degree in playwriting … and doesn’t know what kind of work he can get with that. He applies to random jobs, including one as a security guard (which he doesn’t get). “I was very scared and uncertain,” he recalls, “and I just needed something to try to make sense of things and my place in the world.” So while living in an apartment in Jamaica, Queens, where rent was $400 a month, Jackson writes a monologue called “Why I Can’t Get Work.”

2004

The first song.

NYU postgrad days.

Jackson enters NYU’s graduate program in musical-theater writing. He’s played piano since he was 8 but has never written a song. In class one day, a peer of Jackson’s, Darius Marcel Smith, who is gay, performs an original song about having a one-night stand and then feeling guilty about it and asking God for forgiveness. Jackson jots down a phrase in his notebook: “All those Black gay boys I knew who chose to go on back to the Lord.” That line, plus Tori Amos’s song “Pretty Good Year,” inspires him to write “Memory Song,” a collection of snapshots about growing up as a Black gay teen in a homophobic environment. It’s the first song he has ever written and will be the first song made for A Strange Loop. (The musical will go on to be dedicated to Smith, who died in 2019.)

2006

Jackson performs his songs for the first time.

Maria Manuela Goyanes, a producer at the Public Theater who had previously directed a short play of Jackson’s, suggests that he combine “Why I Can’t Get Work” with the songs he has written. Goyanes invites Jackson to present what he’s now calling Fast Food Town Off Broadway at Ars Nova. The one-man show opens with “My name is Michael R. Jackson. I’m an usher at Disney’s The Lion King. I need the money. I’ve never had a steady boyfriend. Welcome to my shithole. Of joy. And regret.” Jackson performs on piano and is accompanied by a guitarist. There are 20 people in the audience; two walk out. Jackson no longer wants to center the show on his performance, realizing, “It needed to not be a cabaret act. I wanted it to be a musical. But I didn’t know how to do that.”

2007

Enter two important friends.

A number of pivotal people attend an industry reading of Jackson’s graduate-thesis musical, Only Children, based on Frank Wedekind’s play Spring Awakening — crucially, he meets actor John-Andrew Morrison and director Stephen Brackett. Jackson would later ask Brackett to direct his concerts at Joe’s Pub and the West Bank Cafe and Morrison to be in those shows, specifically to sing a piece called “Periodically.”

Jackson with his mother.

The partial ballad is based on a voice-mail that Jackson’s mother left for him on his 26th birthday as well as comments she’s made over the years about how homosexuality is a sin. It’s dramatized in the song as such: “All of these Hollywood homosexuals/Lance Bass, Doogie Howser, T.R. Knight / Stickin’ their things up each other’s buttholes/I’m tellin’ you, son, that it just ain’t right!” Aside from the actor names, the lyrics remain largely unchanged.

Morrison, now Tony nominated for Best Featured Actor in the musical, still does not know why Jackson cast him as his mother, but having listened to her voice-mails, he has a special understanding of her: “Even though she was fussing at him, what I heard in her voice was this deep, deep, deep love for her child. That was always important to me to convey.”

2011

An email from Liz Phair.

From 2007 to 2011, Jackson turns Fast Food Town into a concept musical in the vein of Company and Passing Strange. He scraps all of “Why I Can’t Get Work”; the main character is renamed Usher. By 2010, Jackson has retitled the show A Strange Loop, inspired by the final track on Liz Phair’s 1993 debut, Exile in Guyville, itself a response to the 1972 Rolling Stones album Exile on Main St., as well as Douglas Hofstadter’s concept of a strange loop. The story is now about Usher trying to write a musical and get the rights to Phair’s songs; its score is a mash-up of Jackson’s songs and Phair’s.

In real life, Jackson is also trying to get Phair to say yes to his musical. In 2011, she responds in an email. “You need to write your own songs. I didn’t use the Rolling Stones’s songs to do Exile in Guyville. I wrote my own and you should do the same,” Jackson recalls her saying. He tosses his Phair mash-ups but preserves her influence throughout A Strange Loop; one song, “Inner White Girl,” references Phair’s “Perfect World” in the lyric “They get to be cool, tall, vulnerable, and luscious.”

2012

A vital conversation.

Jackson asks Brackett to direct a workshop of A Strange Loop at NYU. Over coffee, Brackett makes an important suggestion: “What if we cast the show with queer Black actors to populate all of the people that surround Usher?” Brackett had been inspired by Morrison singing “Periodically.” “It was very clear that Michael was writing something that was not about a slice of life,” he says. “It was trying to get inside the head of how this protagonist sees himself in the world.” The supporting characters become known as Usher’s Thoughts. Brackett is later nominated for a Tony Award for his direction.

2014

The time they almost gave up.

A Strange Loop is stuck in a frustrating loop of revisions, workshops, rinse, repeat — with no theater willing to actually produce the show. Meanwhile, aside from Jackson, who got an occasional stipend that didn’t even cover his rent, no one on the team was getting paid to work on the musical. Brackett and Jackson grew fatigued. “It just felt like people weren’t taking it seriously,” Brackett says. “I remember one moment in particular where Michael was like, ‘Maybe I should just give up,’” which Brackett advised against. Jackson doesn’t remember that conversation, but he does recall feeling “discouraged all the time” and left with no other options: “The thing about me giving up was that I did not have a plan B. So to give up would be to do what? I have to make this work.”

Sometime in 2014 or 2015 (Jackson can’t quite recall)

A breakthrough in therapy.

A Strange Loop now has a beginning and a middle — but no ending. And Jackson’s having a personal crisis. His day job at an ad agency is “sucking the life” out of him. His own thoughts are bringing him down: “I’m too fat. And I’m ugly. And boys don’t like me. And no theater will do my work.” Then, one day in Gestalt therapy, a breakthrough: “We arrived at this moment where I had to say to myself, Nothing’s wrong with you; you’re a good guy … There’s nothing inherently flawed about Michael R. Jackson.” The discovery unlocks Usher’s arc for Jackson. “Usher wanted to change. He wanted to do whatever he could to get out of his skin,” Jackson says. “The end would only come when he realized that there was nothing wrong with him.” It leads Jackson to the final song in A Strange Loop, its title song, in which Usher sings, “Maybe I don’t need changing / Maybe I should regroup / Cause change is just an illusion … Then what a strange loop.”

2015

The porn studio where it happens.

Jackson meets trans actor Shakina Nayfack, who tells him she is starting the Musical Theatre Factory, a place to develop new work. MTF gives Jackson and his crew space to workshop A Strange Loop for two weeks. Located above the old Drama Book Shop on West 40th Street, the space also happens to house a working gay-porn studio, Raw Fuck Club. Recalls Morrison, “There were these curtains, and if you opened them, there’d
be, like, slings and fuck chairs. And sometimes the elevator wouldn’t work, so we’d go up these four flights of stairs. And it was cold, oh my God! We’d be in there with our coats on, singing ‘AIDS Is God’s Punishment’!” But when they present the musical to the audience of “40, maybe 50” people, there is a sense that Jackson had struck gold. “Jaws dropped to the floor,” Morrison says. “And afterward, people were coming up to us like, ‘I had never seen anything like that! I didn’t know how to feel. What did you just do?!’”

2016

Enter the angel investor.

Rehearsals.

A Strange Loop has yet another workshop, this time at the Off Broadway venue Playwrights Horizons on West 42nd Street. In the audience is Broadway producer Barbara Whitman (who did the Tony-winning Fun Home). She becomes “mad” that theaters have failed to produce this kind of “challenging” work and steps up to do so. Relatively quickly, three Off Broadway theaters offer to produce A Strange Loop. The team chooses Playwrights Horizons (the site of the original production of Stephen Sondheim’s Sunday in the Park With George), joining its 2018–19 season.

2018

Last-minute revisions in the Catskills.

Jackson goes on a retreat in the Catskills with Brackett and choreographer Raja Feather Kelly. Kelly has an important conversation with Jackson, questioning the opening number of the show, which to him made no sense. A Strange Loop’s opening number, “Intermission Song,” set at a performance of The Lion King, had Usher dealing with annoying patrons and their myriad complaints: Someone spilled Sprite on their baby, the seats were too small, and “I can’t find my brand-new American Girl Place doll!”

Kelly can’t remember who first said the instantly memorable phrase “big, Black, and queer-ass American Broadway show,” which is now the de facto tagline for the show, “but when they did, it was like, Isn’t that then what we should be saying?” says Kelly. “Why not just say what it is that we’re doing? If we’re making a big, Black, and queer-ass American Broadway show, we should say it.” Upstate, Jackson presents a completely rewritten “Intermission Song” that blows Brackett and Kelly away. Instead of listing tourist complaints, “Intermission Song” now introduces the Thoughts and Usher’s central dilemma: how to write a musical, but not just any musical: a — well, you know.

2019

A Strange Loop premieres.

The show debuts at Playwrights Horizons, produced in association with from Page 73, another Off Broadway producer. The reactions are rhapsodic. Adam Greenfield, who now runs Playwrights Horizons but at the time was the associate artistic director, recalls seeing the first run-through of the show — finally fully realized onstage — alongside Whitman. They shared mind-blown reactions. He now has a theory why the musical took so long to get produced: “Its strength is that you see the play and say, I’ve never seen anything like this. But that’s also what makes it harder for works like A Strange Loop to find their home. Theater’s an old dog; it’s often hard to teach new tricks.”

After the run, Whitman takes Jackson and Brackett out to dinner, where she pops the question every playwright dreams of hearing: “Do we want to try for Broadway?” You already know Jackson’s answer. Unfortunately, there are no Broadway theaters available in 2020, so Whitman decides to take A Strange Loop out of town for another run with plans for Broadway in 2021. Woolly Mammoth Theatre Company in Washington, D.C. — now run by Goyanes, the early supporter of Jackson’s original version at Ars Nova — agrees to produce it in fall 2020. Of course, COVID-19 will disrupt all theater plans in the U.S. (the show is delayed at Woolly until November 2021); still, the buzz for A Strange Loop intensifies. It wins several major New York theater awards in a year with no Tonys. And then the 2020 Pulitzer for Drama.

That day, May 11, 2020, Jackson gets a text from a strange number on his phone: “Mr. Jackson, this is Tyler Perry. Congrats on your Pulitzer!!” Jackson tweets about the encounter: “I spoke to Tyler today and he said he was gonna beat my ass but he also congratulated me on the Pulitzer win.” (Though Perry, to date, has still not seen the show.)

2021

A star is born.

Larry Owens, who originated the role of Usher Off Broadway to critical acclaim and many awards, leaves A Strange Loop to do film and television (including Abbott Elementary). The musical is now without a leading man. A search commences for the new Usher with an open call in fall 2020, and on July 16 of the following year, an unknown named Jaquel Spivey is cast. It’s the 22-year-old’s first-ever gig, having just graduated from Point Park University in Pittsburgh. Spivey had never seen the show but was a fan of the cast album. To Brackett, because Usher is 25 turning 26 in the musical, Spivey’s newness proved to be an asset: “Jaquel was so open and vulnerable, and his youth was extremely appealing in the part — there was a very real sense of rooting for him and wanting the best for him. And when he came in in person, he blew us away with his presence and command.” The feeling was unanimous. “He was very clearly the choice for us.”

Spivey, meanwhile, is a nervous wreck before making his debut at the Woolly Mammoth. “God, if you can just help me push this one out. I’m very scared,” he remembers thinking opening night. “When we got to the end and the lights went out for that final blackout, a roar just came out of the venue — loud as hell! — to the point that it shook me. I jumped.” By curtain call, anxieties were hushed. “When I did my bow, I was just like, Okay, you got it.” The Tonys agree: Spivey is later nominated for Best Leading Actor in a Musical for his performance.

2022

Finally Broadway bound.

Jackson’s curtain call.

Ten days before Christmas 2021, Whitman gets the call that the Lyceum Theatre is available for spring 2022; A Strange Loop, coincidentally, will debut on the same block as The Lion King. On April 26, after delaying previews for a week due to COVID outbreaks in the cast, the musical finally opens on The Great White Way. Its big night is especially emotional for Jackson — his parents, who first saw it at Playwrights Horizons and loved it, are in the audience. “They were so proud. And they couldn’t believe that people wanted to take their pictures,” he says. “It was so moving and such a confirmation and validation of the time that we’d spent—all the years that I’d struggled and wrote and rewrote and rewrote and rewrote.”

As Morrison puts it, there has probably never been a stranger journey to this stage: “The amount of times we sang in front of music stands and now look! Look at this magnificent thing.” He then adds, with amazement, “From the porn studio to Broadway.”

The Tony Awards air June 12.

Thank you for subscribing and supporting our journalism. If you prefer to read in print, you can also find this article in the June 6, 2022, issue of New York Magazine.

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