Why ‘A Strange Loop’ is Essential Listening For Pride 2020

Graphic by the author.

A light musical leaves you standing in your seat, clapping uproariously at the joy you just witnessed onstage. A heavy musical — one that tackles tough subjects such as disease, mental health, or anti-Semitism — may engender more somber curtain call reactions, but their themes burrow deep into your thoughts well beyond the closing act.

Pulitzer-Prize winning A Strange Loop, which premiered Off-Broadway in July 2019, is a deeply sad musical, but it is also funny, thought-provoking, and surprisingly earwormy. Its title derives from a cognitive science principle, and its musical sources range from Liz Phair to Stephen Sondheim. Yet, despite its varied inspirations, Michael R. Jackson’s A Strange Loop is a unique story about Black, queer male identity and discrimination. The original cast recording is a particularly well-suited album for Pride 2020: a time in which society is reckoning with the ways that homophobia and anti-Black racism are deeply intertwined. 

Most of the songs sound like introspective journal entries, coloured with intricate rhymes and pop culture references ranging from Moonlight to The Normal Heart.

A Strange Loop tells the story of Usher, a Black, gay musical theatre composer working as an usher for Disney’s The Lion King while he attempts to write his first show. He aims to write a piece about a Black, gay musical theatre writer, working on a show about a Black, gay musical theatre writer, working on a show…etc. Despite sounding like a socially conscious Inception, the show is really about Usher’s self-loathing, complex familial relationships, and sexual frustration as he navigates contemporary life as a Black, queer person. Most of the songs sound like introspective journal entries, coloured with intricate rhymes and pop culture references ranging from Moonlight to The Normal Heart.

Usher’s Inner Thoughts are embodied by a choir of six Black, queer-identifying men. These men play a cast of characters in Usher’s life, from his parents, to his slimy agent, Mr. Fairweather, to abusive one-night stands he meets on dating apps. Usher himself is played by Larry Owens: an actor with self-described “princess syndrome” who sings with a powerful, full-bodied voice. To get a taste of Owens’ commanding presence, watch him perform “Inner White Girl,” a song about Usher both resenting and yearning for white privilege.

Throughout the 59 minute cast recording, we listen to Usher attempting to overcome writer’s block and community pressure in order to write something truly authentic. In “Today,” Usher sings about his writing process while constantly being interrupted by his various Thoughts, such as his “daily self-loathing” or the “supervisor of [his] sexual ambivalence,” who aim to trap him in a cycle of self-hate. In “Writing a Gospel Play,” Usher is encouraged by his agent to write a play with traditional, Christian themes in the style of acclaimed writer Tyler Perry, whose work Usher despises. 

Of course, providing commentary on a cast recording while having never seen the live show has its limitations. Mainly, listening exclusively to a soundtrack ignores essential context that makes an onstage production tick, including choreography, staging, and the show’s book (the scenes that take place in between the songs). I can only glean so much from listening to Larry Owens sneer about his frustration working as a Broadway usher, and I don’t know how the ghosts of Harriet Tubman or James Baldwin in “Tyler Perry Writes Real Life” are presented on stage.

Jackson holds nothing back when it comes to condemning the cold-blooded discrimination and social hierarchies that fester in the gay male dating world.

I am also a white person, and I am writing about a work of theatre that is specifically about a Black, queer person’s experience. Usher’s positionality is especially evident in “Exile in Gayville,” a four minute number in which his Thoughts play various callous men Usher encounters while swiping through Grindr. Describing the song as “critical of gay culture” would be an understatement. Jackson rages about the casual racism and body-shaming that dominate contemporary dating apps today. A standout lyric is one particular couplet, sung by Usher towards the end of the number: “So why don’t you just ravage me / With your white, gay Dan Savagery?” Jackson holds nothing back when it comes to condemning the cold-blooded discrimination and social hierarchies that fester in the gay male dating world.

A Strange Loop critiques from all angles, though. Songs about racism in Usher’s adult life exist alongside songs about homophobia among Usher’s community back home. Usher’s parents love him deeply, but they both vocally disapprove of his sexual orientation. In “Periodically,” an endearing birthday voicemail from Usher’s mom devolves into a diatribe condemning his homosexuality. A listener can sense the scathing hate lurking in the singer’s voice, but it’s buried underneath an earnest and embracing love for her son. This juxtaposition is made all the more dizzying by the fact that this homophobic rant is sung by a Black, queer man. A Strange Loop casts mirror upon mirror on itself, as the audience tunnels deep into the root of Usher’s discontent.

The milestone comes at a time when Black Lives Matter and anti-Racism have seeped into our news cycles and dinner table conversations.

Michael R. Jackson’s A Strange Loop is a contemporary musical that speaks to this current political climate. In May of this year, Jackson won The Pulitzer Prize for Drama, marking the first time in which the prestigious award has been presented to a Black writer. The milestone comes at a time when Black Lives Matter and anti-Racism have seeped into our news cycles and dinner table conversations. Today, a show about how racism and homophobia affect a Black person’s self-image feels more urgent than ever. While A Strange Loop’s brutal honesty may not make for easy listening, Jackson’s story illuminates how forces of race, religion, and sexuality keep minority storytellers trapped in the margins. Then, Jackson uses the medium of musical theatre to afford these stifled voices the chance to sing.

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