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It had to be around here someplace, but Michael R. Jackson could not readily locate his Pulitzer Prize certificate when an importuning visitor asked for a look. He rummaged through piles of paper on a closet shelf. Not there. He inventoried the plastic storage boxes in that same closet, but came up empty again.
“It was, like, in a cardboard folder. What did I do with it? What did I actually do with it?” Mr. Jackson said, casting about his two-bedroom condo sublet in Washington Heights and looking stricken. “I could not have thrown it away. This is now going to torture me for the rest of my life.”
Do not judge. Do not “tsk-tsk” about carelessness. Of late, it has been a wild loop-the-loop ride for Mr. Jackson, 41, the author and composer of “A Strange Loop,” the hit Broadway show. The metafictional chronicle of an overweight, gay Black man writing a musical about an overweight, gay Black man, “Loop” won the 2022 Tony Award for best book of a musical and the Tony for best musical, to say nothing of the 2020 Pulitzer for drama. (The errant document eventually turned up atop a bookcase in the second bedroom, near photographs taken by Jill Krementz of Mr. Jackson’s proud parents at the opening-night performance of “A Strange Loop” and of the playwright himself during the opening-night curtain call.)
“I’ve been traveling so much. I’ve been doing press and running in and out for the last two months,” Mr. Jackson said. “It was, ‘Throw this suit on! Take that suit off!’ It was like a cartoon, clothes flying left and right, and me running out the door.”
Michael R. Jackson, 41
Occupation: Playwright and composer
Designated designer: “I hated every second of choosing furniture. This is the kind of thing I’m just not interested in. I want it to be done. I just want to be at a point where I can appoint a person who knows me really well and knows my taste to do their thing.”
“The apartment was starting to look like a crack den, and I had to bring my attention to cleaning,” he continued. “I got the housekeeper to come yesterday, and we sort of tag-teamed, but there was still a lot to do.”
Mr. Jackson moved into his current quarters in May 2021. For the preceding 16 years, he lived around the corner, in a crepuscular three-bedroom rental with a rotating cast of apartment mates, minimal furniture and — for the first few months of the pandemic, thanks to an issue with a gas line — an out-of-commission stove.
“It was cheaper to live there, but it just got sort of painful to me personally. I’m not as young as I once was,” Mr. Jackson said. “I was like, ‘I want to live alone.’”
He was determined to stay in the neighborhood — “I find this to be a peaceful space” — but seemed uncertain about the process of securing new housing or, more likely, was just too busy to engage. Accordingly, the lead producer of “A Strange Loop,” Barbara Whitman, recommended Bohemia Realty Group, a niche agency that caters to the New York theater community and specializes in rentals and sales in the northern precincts of Manhattan.
The floor-to-ceiling windows in the living room and the views of the Hudson River and the George Washington Bridge from the compact balcony were all that a certain prospective tenant could desire. The roof deck was value added.
“I’m a big fan of sunlight and windows, which I did not have in my old place, which for 16 years was so distressing to me,” said Mr. Jackson, who was also impressed with the primary bathroom. “It’s the nicest I’ve ever had, and I don’t have to share it with anyone.”
The décor is a crucial step up from Ikea — anodyne good taste, in shades of sienna and blue-gray, with a pop of burnt orange. The weighted Afghan on the ottoman, a true security blanket, adds texture.
“I’ve always sort of lived like a college student,” Mr. Jackson said. “And so when I was able to upgrade a bit, I needed some help to figure out some basic things.”
Arnulfo Maldonado, the set designer for “A Strange Loop,” became the furniture whisperer, presenting various options to his decidedly low-maintenance client.
“I said, ‘I need a couch,’ and Arnulfo said, ‘You need a rug under the couch,’” Mr. Jackson recalled. “It would never have occurred to me to put a rug underneath the couch.”
Perhaps more to the point, it would not have occurred to him to buy a rug.
“I do not have an interior-design bone in my body,” said Mr. Jackson, who vows to raise his game when he buys a house — something he hopes will happen in the next few years. “I couldn’t tell you whether I prefer neo-Classical to neo-non-Classical. I don’t know any of that. It isn’t something I’ve ever had to think about.”
Of course, he has his discrete spheres of expertise. He waxes Talmudic on what he calls his trifecta of “Inner White Girl Inspirations.” Said trifecta comprises a framed poster of Joni Mitchell’s “Dog Eat Dog” album, which hangs over the sofa; a signed vinyl copy of Liz Phair’s “Exile in Guyville,” an opening-night gift from his agent (“This put Liz Phair on the map,” he said. “It blew the roof off the indie rock scene at the time — it’s a really iconic album”); and a vinyl copy of Tori Amos’s “Under the Pink.”
“The first song on the album is ‘Pretty Good Year,’ and when I sat down to listen to it in high school, it really changed the game for me in terms of the kind of art I wanted to be making as a writer,” Mr. Jackson said. “She opened up a whole world of thought for me.”
He is similarly steeped in the fine points of daytime dramas. “I was a huge soap person,” he said. “I watched all of them, or most of them. I had a subscription to Soap Opera Digest. I came to New York initially to become a soap opera writer. I interned at ‘All My Children’; I interned at ABC Daytime.”
During lockdown, Mr. Jackson was able to rewatch many of the sin-and-suffering-in-the-afternoon episodes he had recorded years earlier, courtesy of the still-functioning TV-VCR combo his father bought him just before his freshman year in college.
Without fanfare, he sat down at the Yamaha keyboard in the second bedroom and played a lovely stretch of melody from “White Girl in Danger,” a musical in development that is drawn in part from his love of soaps.
“I do think having a nice setup does make me feel less stressed when I’m working, which is good,” Mr. Jackson said. But he insisted that his previous apartment, gloomy though it may have been, did not impede the progress of “A Strange Loop.”
“It didn’t matter,” he said. “My whole life was writing all the time and working on the piece. I had to write. I had to get it done.”
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