A Strange Loop's Michael R. Jackson On His Creative Process

A Strange Loop is undeniably a success story. When the musical—which follows the interior life of a young, gay, Black theater usher named, what else, Usher—premiered off-Broadway in 2019, it was a hit, winning a trove of awards, including the Pulitzer Prize for Drama, for its playwright, composer, and lyricist Michael R. Jackson. After a lauded run at the Woolly Mammoth Theatre Company, in Washington, DC, A Strange Loop has landed at Broadway’s Lyceum Theatre. Jackson never imagined things would happen this way.
“When I began working on this show, it started off as a monologue I wrote for myself to create a life raft at a very uncertain time, and it grew from there,” Jackson says. “For it to have evolved and become this, what it is now, is exciting, terrifying, and -bewildering—and I’m into it.”
Here, he opens up about his process for our peek inside the habits of masterminds.
How do you prepare yourself to be creative?
Taking a walk is helpful to free my head up.
At what time of day do you prefer to work?
It used to be the nighttime, but as I’ve gotten older I’m more of a morning person.
What one element is necessary to your process?
Between my Notes app and my voice memos, my iPhone is crucial.
What to you most often do to procrastinate?
I watch YouTube videos. The one I go to the most is One Life to Live, in particular when Judith Light was on it. Her character was beleaguered, and Judith let us have it with all her might.
How do you take your coffee?
I don’t drink coffee. For me, it’s water, whiskey, wine, or smoothies.
What place is most conducive for you to work?
My office. Though I found that when I was at the Hermitage Artist Retreat in Florida, being right on the beach got my juices flowing.
Who’s your favorite collaborator?
I love all my collaborators the same. Let me rephrase that: I don’t love them all the same, but I love them all equally.
It’s said that genius is one percent inspiration and 99 percent perspiration. What is that ratio like for you?
The perspiration is the inspiration. Putting in the effort sparks all the ideas.
What’s your dream project?
A Carpenters jukebox musical.
What have you learned from a failure?
My failures have all helped me strengthen my craft, my point of view, and my artistry in every way. I’m a big fan of failure.
What’s been your favorite creation thus far?
A Strange Loop. It’s the piece that’s been with me the longest, that I put the most into, and from which I’ve had the greatest creative and artistic fulfillment.
This story appears in the April 2022 issue of Town & Country. SUBSCRIBE NOW
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