fi rst he has to fi nd some peace with
his fl aws, whether real or imagined.
It took Jackson decades to achieve
the kind of clarity that Usher yearns
for and to distill it into this play. ‘‘The
only reason why I come to any of
these conclusions is because I spent
almost 20 years working on one piece
of art,’’ Jackson said. ‘‘And the exer-
cise of that forced me to have to real-
ly be thoughtful and really be open to
changing my mind. I’ve changed my
mind so many times with new infor-
mation coming along.’’ This thought
eventually took him to a Joni Mitch-
ell lyric, from her 1985 song ‘‘Dog Eat
Dog,’’ which he quoted to me after
breaking into an improvised medley
of her deep cuts: ‘‘Land of snap deci-
sions/Land of short attention spans/
Nothing is savored/Long enough to
really understand.’’
Jackson, who is 41, was born and
raised in Motown. Growing up
‘‘middle middle-class’’ in Detroit in
the 1980s and ’90s, he had what he
calls ‘‘a normal external childhood.’’
His father was in the police force for
27 years before he retired to work
as a security consultant for General
Motors, and his mother worked in
the accounts-receivable department
of the automotive manufacturer
American Axle. His brother, who
is four and a half years older, took
him to see horror-comedy fi lms like
Rusty Cundieff ’s ‘‘Tales From the
Hood.’’ They all went to First Glory
Missionary Baptist Church, where
his mother was a secretary and his
father a trustee. Jackson sang in the
main choir and played piano for the
Sonshine Choir (for little kids) and
the Inspirational Choir (for older
women). He appreciated church as
kind of a workshop; it gave him a
chance to hone his craft. ‘‘It was just
a place for me to play music and to
teach songs, and it was almost like I
was playing in a jazz club or some-
thing. I was building my musicalchops playing in front of an audience
and for choirs every Sunday.’’
Pop culture suff used his life. He
attended Cass Technical High School,
where the legends of alumni like
Diana Ross, Lily Tomlin, Ellen Burs-
tyn, Jack White and Kenya Moore
haunted the hallways. Jackson’s
preteen bedroom was covered with
autographed photos of his favorite
celebrities that he’d sent away for:
Macaulay Culkin, Jasmine Guy,
Kadeem Hardison, Anna Chlumsky,
Emilio Estevez and Tim Allen, or
‘‘whoever was on some TV show
or movie I was watching.’’ In high
school he drafted award- winning
poems and worked on a literary jour-
nal. Even then, his thinking resisted
easy judgment and retained the rightto take its time. In a passage in his
journal marked by strikethroughs
and scribbled-out ink, he wrote
about O. J. Simpson’s 1997 civil trial
for the death of his ex-wife Nicole
Brown: ‘‘I don’t know how I feel. At
fi rst, I thought he was innocent. Then
during the civil case, I thought he was
guilty — in both cases I didn’t care
whether he did it or not. I resented
the fact that people assumed he was
either totally capable of murder or
not capable of murder.’’
While his external circumstances
were comfortable, internally he was
struggling with accepting his sexual-
ity. When he came out to his parents
at 17, they confronted him; Jackson
says his father asked his son, passive-
aggressively, if he was attracted to
him, a moment Jackson reprises
in ‘‘A Strange Loop.’’ (He’s on really
great terms with his parents now.)
It was around this time that Jack-
son was fi rst introduced to what he
calls ‘‘white-girl music’’ after hisPhotograph by Malike Sidibe The New York Times Magazine 41
Jackson overlooking
the set at the
Lyceum eater
in April.