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Why The Pulitzer Win For ‘A Strange Loop’ Is Historic—On Multiple Levels

Lee Seymour

After weeks of dispiriting press releases and grim cancellations, Theater Twitter was positively buoyant Monday afternoon as Michael R. Jackson (no relation) received the 2020 Pulitzer Prize for Drama for his musical A Strange Loop.

“It’s like all the holidays rolled into one,” tweeted Jamie DuMont, who hosts the Broadway podcast The Fabulous Invalid.

“It’s honestly the most I’ve seen my timeline rejoice collectively in two months,” agreed Casey Mink, senior writer at Backstage Magazine.

Many others followed suit, most in terms too joyfully explicit to print here.

The adulation speaks both to the industry’s support of the young writer, who’d been developing the show for over a decade, and also its doubly historic status in the Pulitzer canon.

Jackson’s win marks the first time the committee has awarded a black writer for a musical. (A Strange Loop is the tenth musical to take home the prize, following such hits as Hamilton and Rent). That’s particularly poignant given the material itself: a discursive meta-tale about a young, gay, black musical theater writer, who’s writing a musical about a young, gay, black musical theater writer, and so on down the rabbit hole.

(Jackson himself refers to the show as self-referential, not autobiographical, as he does not appear in it. The lead, named Usher, is played by powerhouse Larry Owens).

It is also the first musical to be awarded the Pulitzer without having had a Broadway production. A Strange Loop premiered last summer Off Broadway, at the nonprofit Playwrights Horizons, and has since been shepherded by veteran producer Barbara Whitman, with an eye toward the Rialto.

But initially, the material - cerebral and unapologetic, exploring the intersection of race, religion, and sexuality - was seen as riskier than traditional commercial fare, which tends to be dominated by film and TV adaptations. Pretty Woman it was not.

Much to the delight of underdogs everywhere, the Off Broadway run sold out in a heartbeat, and the show has since been nominated for a slew of other awards. (It was one of the best things I saw in a theater last year).

As for Broadway? Conventional wisdom might have you believe that only recognizable brands have a shot at making bank. But Whitman has a history of shepherding and supporting other “unlikely” hits, including Fun Home and Next to Normal (the latter of which won the Pulitzer in 2010).

A Strange Loops recognition, and the buy-in from major backers, is well deserved. It also highlights the industry’s structural challenges, as well as the forces working to change them.

Yes, many Broadway musicals take the form of glitzy film adaptations or jukebox bioshows. It’s often easier to raise money for them. Investors find it less frightening to back something they (or their kids) can recognize.

But if you look in aggregate at the last five years’ worth, the ones based on pop catalogues or megabrands fared far worse than original material. Since 2015, one in three fresh-minted tuners have turned a profit. But familiar adaptations like Frozen and Tootsie? Only about one in eight.

Also under the microscope here is the content pipeline itself, and a generational shift affecting all industry echelons. Nonprofits help develop new work, particularly shows that challenge power structures and mores, like A Strange Loop, shielding them from commercial vagaries until they’re ready to go on the open market.

Slave Play and What the Constitution Means to Me are two such shows that transferred to Broadway last year. Judging by Constitution’s wild commercial success and the cultural depth charge Slave Play set off, Broadway’s gatekeepers - and audiences - are more willing than ever to embrace material that makes traditional investors balk.

(The recognition of another Pulitzer finalist, cultural critic Soraya Nadia McDonald, underscores this shift further; McDonald has written extensively and influentially about the transforming intersection of race and art, including Slave Play).

The coronavirus pandemic could change all that. These smaller nonprofit institutions will be hardest hit by the shutdown, crippling the ability of artists like Jackson to find their voice, and their success. The support network for emerging artists, and the clout of producers willing to take risks on them, will be deeply damaged. As I’ve written elsewhere, the industry needs a bailout, and fast.

In the meantime, we can - and should - still celebrate work like A Strange Loop, and the institutions that champion it. The other finalists for the Drama prize were also, not incidentally, presented by Off Broadway nonprofits. Will Arbery’s play Heroes of the Fourth Turning was also produced at Playwrights Horizons; Soft Power by David Henry Hwang and Jeanine Tesori, premiered at The Public Theater, which incubated a certain seminal hit named Hamilton.

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