Every black person in America knows the intermittent lure of race
denial. Bert Williams argued it well in his seminal essay “The Comic
Side of Trouble,” in American Magazine, in 1918: “I have never been
able to discover that there was anything disgraceful in being a colored
man. But I have often found it inconvenient—in America.” This
incisiveness is especially heartbreaking coming from the vaudeville
pioneer who made a living darkening his face with cork—a black man
passing for blacker. His friend W. C. Fields famously said of Williams,
“He was the funniest man I ever saw, and the saddest man I ever knew.”

William Pickens, the brown-skinned field secretary of the N.A.A.C.P. in
1927, also understood the allure of race denial: “If passing for white
will get a fellow better accommodations on the train, better seats in
the theater, immunity from insults in public places, and may even save
his life from a mob, only idiots would fail to seize the advantage of
passing, at least occasionally, if not permanently.”

Pickens’s brother-in-arms, Walter White, the N.A.A.C.P. executive
secretary from 1931 to 1955, a black man who was a-hundred-per-cent
white-looking, could not have agreed less. In some respects, one could
argue that White had spent his life passing for black. As he wrote in
his autobiography, “A Man Called White,” “I am a Negro. My skin is
white, my eyes are blue, my hair is blond. The traits of my race are
nowhere visible upon me.” White’s honesty was admirable, and the
questions he raised about blackness as culture versus physiognomy were
asked again by Rachel Dolezal, the former and now disgraced white
president of the N.A.A.C.P.’s Spokane, Washington, chapter.

I’ve been obsessed with White since I started researching him, for the
chief villain in a film I’ve been writing about “Amos ’n’ Andy,” the
most popular radio show of all time, which was created and voiced by two
white men, Freeman Gosden and Charles Correll, who for over thirty years
passed for black on radio. Though they never hid their true identities,
the two men were constantly surprised by how many fans of all races were
convinced they were actually black.

When the show finally came to TV, in 1951, CBS flirted with the idea of
using white actors in blackface, or Gosden and Correll voicing the parts
while unknown black actors mouthed the words. Eventually, CBS was forced
to cast black actors in the roles. Spencer Williams, the brilliant
director of “Blood of Jesus,” would suddenly rocket to mainstream fame
as TV’s Andy Brown. He complained to Gosden, when Gosden tried to
instruct him on how to sound more “colored,” “You mean to tell me a
white man is trying to teach a Negro how to act like a white man acting
like a Negro?!”

Williams’s dilemma is still familiar to every nonwhite actor who’s ever
auditioned. White directors and casting directors routinely ask them to
accent their accents, if they have them, but, more typically, the actors
are asked to adopt one from a trunk full of tired types, to pass as
exotic when they are anything but. From Williams’s lament to Robert
Townsend’s “Hollywood Shuffle” to Aziz Ansari’s “Master of None,”
progress has been glacial to the point of imperceptibility.

In “Amos ’n’ Andy,” Williams wasn’t the only one whose authenticity was
questioned. Early TV was, of course, in black-and-white, and Alvin
Childress, who played Amos, was a light-skinned black man. After a few
episodes, CBS was afraid that in black-and-white Childress could be
confused for the latter, integrating the show, so they insisted on
ridiculously dark face makeup for him. When you watch reruns on YouTube,
look for the line on his neck where the brownface ends.

Passing entered my work again in my latest play, “Satchel Paige and the
Kansas City Swing.” It tells the story of Paige, one of baseball’s most
legendary pitchers, and his bittersweet, complicated journey from the
Negro Leagues to the majors. When Paige was young, the white M.L.B.
scouts were desperate to exploit his talent and that of his
peers. If the black ballplayers were light enough, they would send them
down to Cuba, have them learn a little Spanish, apply a lot of
skin-lightening cream, and pass them off in the M.L.B. as exotically

In fact, there was a team, the New York Cuban Giants, made up entirely
of African-Americans who would speak rapid-fire, accented gibberish to
each other on the field to convince white crowds that they weren’t
garden-variety black Americans.

My obsession with all these historical subjects stems from my own
history of multivariable passing. Édouard Manet’s painting “A Bar at the
Folies-Bergère” was an early revelation—perhaps the first time I looked
at a work of art and it looked back at me. It was my absolute favorite
painting in the Masterpiece board game that my doctor- and
lawyer-in-training parents got for my sister and me to trick us into
absorbing high culture. No Chutes and Ladders—my black tiger parents
(“A B is an F!”) bought us a children’s board game about art history.

What resonated within me most about this overanalyzed Manet wasn’t the
obvious trick of painting a mirror image: the barmaid’s sad gaze at the
creepy rich guy (Manet himself?) ogling her sadness while the dissipated
frolic in the background. What struck me instead was a sense of
perspective. Subject and object. How are we seen as we see. I couldn’t
help thinking of the barmaid as me posing for my yearly
elementary-school photos. Inside, I felt like all the other Italian,
Irish, and Jewish kids. Inside, I was unconsciously, seamlessly passing.
But as soon as the photo arrived in the mail even my first thought
was, What’s he doing there? That goofy-looking black kid. The photos
always triggered a song in my head: One of these things is not like the
others, one of these things doesn’t belong . . .

The realization started shaping me. No matter how I was feeling that
day—nerdy, right-handed, gassy—the only descriptor that would ever
really matter would be my race. I was born in 1962, at what was then
Freedmen’s Hospital, in Washington, D.C., founded precisely a century
earlier. Freedmen’s, next to the campus of Howard University, was the
first hospital whose explicit mission was to treat former slaves. My
father was a med student at Howard, and we lived across the street.
Freedmen’s was probably the most unadulteratedly black place to be born
this side of Harlem Hospital.

Things have been more mixed and murky ever since. My family moved from
black Dayton, Ohio, to blacker-than-black Detroit in ’65, and then to
Ypsilanti, Michigan, in ’68. In Ypsi, in our neighborhood of
still-being-built fake-Tudor and semi-attached town homes, half of the
families were young professionals or affiliated with the University of
Michigan, while the other half had dads working for G.M.’s oceanic
Willow Run assembly plant. Maybe a third of us were black. The
development and the town was mixed enough that no one side could claim
cultural hegemony. For acceptance among my friends, no one had to pass
as anything except a great Hot Wheels track assembler.

When my father accepted a job as a psychiatrist to Yalies at their
student health services, my parents could have moved us into New Haven
proper, sort of a Detroit in miniature and boasting one of the highest
per-capita homicide rates in the nation. Instead, they moved to one of
its suburbs, Hamden, and the white part of Hamden, to boot. They told us
it was because they heard that the schools were good for my sister and
me, which of course was part of it. But I suspect that, as
second-generation college-educated black snobs, the most talented of the
Talented Tenth, they also thought that they themselves had earned the
right to escape the inner city.

Also, my mother was an aspiring playwright and a huge fan of “A Raisin in
the Sun,” and I believe the chance to live out that plot was too much
for her to resist. Like Lorraine Hansberry’s Younger family in the late
nineteen-fifties, we Ellises in the nineteen-seventies were suburban
pioneers, the only blacks actually living within the entire Spring Glen
Elementary catchment area. Unlike the Youngers, there were no sidelong
glances from the neighbors that I noticed, no bribes to get us to move.
Or worse. Nobody burned a cross on our lawn when we arrived. That
welcoming was reserved for black families trying to live over in Italian
East Haven, where the news reported about a cross burning every year or

It was here in Hamden, as a true minority for the first time, that I
began my lifetime of various passings. To my new Italian and Jewish
friends, it wasn’t initially my hue that drew their scorn. I was too
new, and my family was so in the news for doing exactly what we were
doing, that my landing among them seemed ripped from the headlines. We
were all living in our own ABC Afterschool Specials, and for the most
part no one wanted to play the racist villain. But they were kids and
had to attack difference, so instead it was my Midwestern flat “A”s they
savaged. My “pa-jam-as,” and “pop” instead of “soda,” sent them
cackling, so not only did I almost instantly erase those features from
my speech, I was soon inserting their New England “Aw, wicked” into
every possible utterance.

Though my sister and I were the only black kids living near school, a
dozen or so other black kids were bused from the more depressed side of
our depressed town. Since they got right back on the buses after school,
I didn’t see much of them. It was about a month after I started that a
black kid casually spat the word “Oreo” my way as he boarded his bus. A
day later a white kid I didn’t know hissed “nigger” while I was
unlocking my bike. I never brought these incidents to my parents. They
would have marched on the school, especially my mom, and dragged me kid
to kid till I snitched. Instead I just swallowed it all and sulked. I
withdrew into the persona of the silent sufferer, the tragic hero, the
Melancholy Black Dane, Monet’s self-pitying barmaid.

At Hopkins, the venerable private day school in New Haven, there were
even fewer black kids than at Spring Glen: a handful of scholarship
kids, and one or two middle-class strivers like myself. I was not good
friends with any of them, convinced that my passing as a colorless,
general-purpose nerd had been so successful that I had personally
ushered the nation into a “post-racial” world decades before the term
even existed.

A few years later I transferred to Phillips Academy, Andover, the
boarding school of the Bushes, the Kennedys, and the Rockefellers. The
school gave every entering black kid the choice of a black roommate. Of
course I declined. How pointless and backward, I thought. When I
arrived, I realized I was only one of two or three other black kids
there who were not from the “A Better Chance” program, kids plucked from
inner cities around the nation. But, unlike at Spring Glen, we were all
smart and thrilled to be living away from home. The AF-LAT-AM(Afro-Latino-American) house threw weekly dance parties with slow
dancing toward the end of the night, so it was the nearness of black
girls that started me sometimes venturing into black orbits. At Andover,
surprisingly, individuality was so revered that groups were relatively
fluid. Everyone, regardless of color or class, was convinced, by their
mere acceptance into such a school, that their uniqueness was valued.
Passing as anything other than yourself just seemed sad.

I arrived at boarding school determined to reinvent myself as the
mysterious new kid. No one was fooled. I then begged my dad for Sperry
Top-Siders. I was at the preëminent prep school, for God’s sake. These
shoes would telepathically instruct the Kennedys to invite me to Hyannis
Port for Thanksgiving. A few weeks later, when my dad came up to visit,
he surprised me with Topriders, plastic-soled knockoffs, the
several-times-reduced price tag from Marshalls still on the box. And in
the box they stayed.

Thanks to the black students I’d met at Andover, I entered Stanford
radicalized. This time, not only did I request a black roommate but the
black dorm, Ujamaa! Actually, it was only half-black by population, but
it was the black cultural hub of campus. I was ready to reinvent myself
again, and this time pass for an anti-apartheid, red-black-and-green
cultural nationalist, a non-bougie, non-boarding-school-educated black
person. Unfortunately, however, my dad’s high-school-graduation present
was a pair of real Top-Siders, and I made the mistake of wearing them to
Ujamaa my first day in college.

A black girl actually stopped me in the hall and gasped.

“What are those on your feet?”

Day One, and I was instantly branded the black preppy Republican/narc
living in a dorm where the R.A. unironically wore a dashiki. It was an
endless and alienating freshman year, and, besides my roommate, my best
friends in the dorm were some of the white kids who were thrown into
Ujamaa by chance and as much outsiders as I was.

The next year I left for the school’s campus in Italy, a Renaissance
villa with manicured gardens on a hill high above Florence. As usual, I
was the only black kid, though there were about seventy of us. Most of
the kids barely spoke the language and left the villa mainly to go to
the train station and travel the continent. I moved out after a
semester, to live in the city with a friend, and not only did I learn to
speak, I affected a Florentine accent that never ceased to make the
natives smile. Like moving from Michigan to Connecticut, being in Italy
triggered my internal chameleon, my autonomic passing reflex.

And I loved it. I moved back to Florence after graduation to finish
“Platitudes,” my first novel, and I got a perverse kick whenever I was
mistaken for something more exotic than an American Midwesterner. I
rented a very small room in Scandicci, a working-class suburb, and I
remember coming out of the alimentari, the Italian version of a
bodega, joking with the owner when an extremely old and twiggy Italian
woman suddenly clutched me and said, “Uno dei nostri Somali!One of
our Somalians
. This was so fucked up on so many levels. The Italians
had colonized Somalia and its neighboring Ethiopia ruthlessly. The
woman’s casual use of the possessive pronoun epitomized the evils of
colonialization, something I knew a lot about, since several of my
friends in Italy were actual Somali students. Nevertheless, I was proud
that I had been able to trick her.

Back in Italy, just out of college, I was only beginning to understand
my ability to choose how I was viewed by others. I imagine Korla Pandit
did it much better. Since then, I have been struggling to perfect the
masks I wear, with the goal of being able, like the members of the
Impossible Mission Force, to reach under my chin and peel them off at

Thirty years later, I am just now coming not to care how I am judged,
not because of some inner strength but the realization of the futility
of caring about it. We’re all judged by such complex matrices that it is
impossible to anticipate them all. I’m only now coming to a place Joan
Armatrading arrived at in 1979, with her lyric from the song “How
Cruel”: “I heard somebody say her black was way too black . . . and
someone answer she’s not black enough for me.”

If you can’t win, stop playing.