cousin studied at Interlochen Cen-
ter for the Arts in 1995 or 1996, and
brought back Tori Amos’s albums
‘‘Little Earthquakes’’ and ‘‘Under
the Pink.’’ ‘‘I was just sort of coming
out at that time and trying to fi gure
things out, and that music hooked
me right in. The language is very
riddlelike, but the music underneath
it is so complex and lush and com-
plicated, and I just kept listening.
And then the second track comes
on: ‘God, sometimes you just don’t
come through.’ And I was like, ‘Oh,
yeah,’ because I was raised in church,
and I was having a lot of questions
about that.’’ Amos’s music ‘‘met me
right where I was at that moment in
time. And because I was also writ-
ing, it gave me permission to start
saying things that I was thinking or
feeling or wondering about in like a
profane sort of way. And so I began
copying her immediately just trying
to fi nd my voice.’’
He also loved Liz Phair and Joni
Mitchell and considers the three
songwriters his own private reli-
gious triptych: Mitchell is the moth-
er, Phair is the daughter and Amos,
Jackson’s ‘‘fi rst love,’’ is the holy
spirit. ‘‘These white women singer-
songwriters inspired me to be my
truest, rawest self,’’ he told me. For ‘‘A
Strange Loop,’’ Jackson wrote ‘‘Inner
White Girl,’’ an ingenious paean to
the emotional and lyrical freedom
those women employ in their music:
‘‘Black boys don’t get to be cool, tall,
vulnerable and luscious/Don’t get to
be wild and unwise/Don’t get to be
shy and introspective/Don’t get to
make noise, don’t get to fantasize.’’
In 1999, Jackson left Michigan to
attend Tisch School of the Arts at
New York University. Shortly after he
graduated, he wrote a monologue, a
vehicle for his career anxiety called
‘‘Why I Can’t Get Work,’’ that became
the kernel of ‘‘A Strange Loop.’’ He
kept writing and developing songs
in Tisch’s M.F.A. playwriting and
musical-theater program, and after
that, all while ushering at the Dis-
ney musicals. Later, he worked at
an advertising agency. Infl uenced
by ‘‘Hair,’’ Wayne Koestenbaum and
Michael Daugherty’s ‘‘Jackie O,’’
Kirsten Childs’s ‘‘The Bubbly Black
Girl Sheds Her Chameleon Skin’’ and
Stew’s ‘‘Passing Strange,’’ Jackson
kept hacking away at the collection
of songs and dialogue that eventually
became the musical, trying to make
something uniquely his own. These
were lonely years for Jackson in New
York City, when he was alternately
not dating and chasing unattainable
paramours, hating himself and fi nd-
ing internal armistice, losing weight
and gaining it back.
As he aimed to fi nish ‘‘A Strange
Loop,’’ the thing that delayed his
progress, he told me, was his own
self-loathing. He could not shake the
feeling that many things were wrong
with him: his gayness, his fatness,
his chosen career path. Because
the play is so self-referential, Jack-
son had to fi gure out his own life
before knowing how Usher fares,
and therefore how the musical ends.
Sometime in 2014 or 2015, Jackson
had a breakthrough. During a ther-
apy session, he was engaging in the
practice of ‘‘tapping,’’ where you
touch various chakras throughout
the body and say, ‘‘Even though [fi ll
in the blank], I completely and total-
ly accept myself.’’ That session, he
told me, ‘‘brought up a sense of grief
for my childhood and how sad I had
been for a long time — feeling like I
didn’t belong or fi t in and being able
to have compassion for my younger
self who was still with me. And hav-
ing that moment was very powerful
and healing in so many ways.’’
Gradually, he realized that noth-
ing was wrong with him, and he
used this insight to unlock the play’s
structure. Usher comes to fi nd that
his negative, self-eff acing thinking
is just a series of spiraling feelings
that he has some amount of control
over. Those thoughts tell a story,
but it doesn’t mean that the story is
true. Jackson’s two-decade process
of writing ‘‘A Strange Loop’’ — and
the many years he spent in therapy —
helped him accept his own questing
mind and the trouble it sometimes
causes him. He’s someone who dis-
dains orthodoxy, someone whose
ex ghosted him after saying, ‘‘Wow,
you’re really not a static thinker.’’
Stew, one of Jackson’s infl uences,
told me that ‘‘A Strange Loop’’ is
in a ‘‘continuum of Black art’’ that
expresses how Black people ‘‘are
complete people who have every
possible thought that could be
had.’’ Jackson himself, Stew said, is
in another tradition. ‘‘I just felt like
his work is so fi rmly in that line
of Black disrupters, of generousdisrupters. Artists that are willing
to go beyond, you know, and sort
of display themselves? I consider
that a kind of generosity and a kind
of bravery.’’ Jackson’s close friend
Kisha Edwards-Gandsy spoke of
the searching, restless quality of
Jackson’s intelligence. ‘‘I feel what
Michael asks everybody is, ‘If you
think you know something, do you?’ ’’One day in mid-March, I arrived in a
Midtown Manhattan studio for Day
3 of rehearsals for ‘‘A Strange Loop.’’
The whole space felt like an extension
of Jackson’s imagination: A miniature
model of the Lyceum’s proscenium
was situated in the background,
along with a few props, including an
empty Popeye’s chicken box. Jason
Veasey, who plays Thought 5, wore
a green shirt with ‘‘Detroit’’ across
the front; Thought 3, John- Michael
Lyles, had on a T-shirt that read, ‘‘Stay
weird and live free,’’ which could be
Jackson’s motto.
The group started rehearsing
‘‘Exile in Gayville,’’ a song about Ush-
er’s relationship to dating apps and
a nod to Phair’s ‘‘Exile in Guyville.’’
Jackson, the actors, the associate
choreographer, Candace Taylor, and
the show’s director, Stephen Brack-
ett, made changes on the fl y. ‘‘Can Iadvocate to make a tiny adjustment
to get a little bit more quickly into
the line?’’ Brackett asked about the
pacing of the Thoughts’ reaction to
Usher calling Beyoncé a ‘‘pop- cul-
ture terrorist’’ (he was paraphrasing
bell hooks). ‘‘If Beyoncé comes, I’m
not going on,’’ Spivey joked.
Later, Jackson and the show’s
choreographer, Raja Feather Kelly,
jokingly compared themselves to
each other and to other Black artists.
‘‘If I position you as me in the
downtown dance world and me as
you,’’ Feather Kelly said, ‘‘in celebrity
culture, we are Kanye West, because
for so long, no one would give us
any attention. And people were like,
‘It’s impossible what you’re doing.’ ’’
Jackson: ‘‘But does that mean
we’re egomaniacs?’’
‘‘I think we have to be,’’ Feath-
er Kelly said, ‘‘I mean, by virtue of
needing to be seen and heard.’’
‘‘Who is our Pete Davidson? Who
is our K.K.W.?’’ Jackson asked, and
Feather Kelly whispered an answer
in his ear.42 5.8.22 Photograph by Malike Sidibe
Jackson, left,
with Jaquel Spivey,
who plays Usher
in ‘‘A Strange Loop,’’
during re^
hearsals.