
“A Strange Loop”: A Daring & Personal Ride—at A.C.T.
Michael R. Jackson Creates Bold, Black, Queer Meta-Musical
by Kim Waldron
“A Strange Loop” is a musical about a Black queer writer writing a musical about a Black queer writer, who happens to be writing a musical about a Black queer writer.
Why does a “meta” musical about a young, self-described “fat,” queer Black man so delight this old medium-sized white CIS woman?
Because it addresses human universals, like fear, insecurity and family? Yes. Because it is playful? Of course. Because it’s over the top and fabulous? Sure. Because the language is raw enough it would have made my salty sailor father blink? You betcha. (Don’t bring the kiddies.)
Most importantly, it’s deeply personal. Every song and every conversation feels intimate and alive. It’s personal for the audience too. Sometimes we all laughed, sometimes we all moaned in sympathy. Other times, I’d snort with laughter and the person next to me sat silent. Then he’d groan aloud when I felt only a small pang of sympathy. We couldn’t help but react to each emotion or experience that touched us.

Malachi McCaskill is brilliant as Usher, the writer trying to pen the “big, Black, queer-ass, American Broadway show.” MaCaskill is on every minute of the musical, always genuine and passionate. He’s endearing and yet clearly damaged. We care.
The six-person Chorus embodies “Thoughts” bedeviling Usher’s mind. The six Thoughts hilariously taunt him and throw shade. Perhaps you’ve met Thought 1, Daily Self Loathing ?
The Thoughts morph into Usher’s family, failed love partners, and surprising complications. They can be funny, or savagely devastating. Each actor is outstanding, making an individual, distinctive impression.
My favorite moments involve Harriet Tubman, the N-word monitor, and several mothers who undermine Usher as he struggles to build his life. Dad is also unforgettable. There’s a lot to choose from, you’ll find your own favorites. Michael R. Jackson strikes gold with his wild and wonderful characters.

“A Strange Loop” uses a simple background made effective, and occasionally dazzling with lighting and sound. One big exception toward the end involves more conventional scenery á la Tyler Perry. I’ll let that manifestation remain a surprise.
There’s no end of laughs in this musical but a couple of the more brutal scenes still haunt me. A bitter sermon in a church, with choir and choreography, is heart-breaking and unforgettable.
Michael R. Jackson wrote book, songs, and lyrics. He’s a master of wordplay, with a sly word here, a gut-busting joke there. You don’t need to take my word for it. “A Strange Loop” won a Pulitzer in 2020 and two Tony awards in 2022. The play flies by, no mean feat at an hour and forty-five minutes with no intermission.

“A Strange Loop” is as meta as it gets. Don’t worry, you don’t need a degree in physics, or metaphysics, to enjoy it—just a capacity to enjoy explicit language and the odd sex act is required.
If you’re not Black or LGBT+ you might miss a reference here or there, but not enough to matter. Any human who has experienced fear or insecurity—and has a family, will understand and appreciate “A Strange Loop.”
Michael R. Jackson dared to write it. Dare to see it.
“A Strange Loop” —book, music, and lyrics by Michael R. Jackson, directed by Stephen Brackett, choreographed by Raja Feather Kelly, scenic design by Arnulfo Maldonado, costumes by Montana Levi Blanco, lighting by Jen Schriever
—at A.C.T, Toni Rembe Theater, San Francisco, a co-production with Center Theater Group, Los Angeles. Info: act-sf.org – to May 12, 2024.
Cast: Jordan Barbour, J. Cameron Barnett, Carlis Shane Clark, Alvis Green Jr, Avionce Hoyles, Tarra Conner Jones, Malachi McCaskill, and John-Andrew Morrison.
Banner photo: J. Cameron Barnett, Tarra Conner Jones, Jamari Johnson Williams, John-Andrew Morrison, Malachi McCaskill, Jordan Barbour, and Avionce Hoyles. Photos: Alessandra Mello