One of my fondest memories from the New School for Social Research Liberal Studies MA program comes from a course titled “Representations of Race and Gender in American Culture.” It was the day, about halfway through the semester, when co-teachers Elizabeth Kendall (author of feminist studies of early modern dance and 1930s screwball comedies, among other books) and Pulitzer-prize-winning critic Margo Jefferson demonstrated the cakewalk, a dance developed in the 19th century by Southern slaves and later picked up at the turn of the 20th by white people who without realizing it were in fact imitating black parodies of their tight-assed selves. Conundrums of race and gender identity in modern America are similarly at the core of Jefferson’s memoir, Negroland.

“Negroland” is Jefferson’s name for that small, privileged segment of black American society alternately known as the “colored aristocracy,” “the black bourgeoisie,” and “Our Kind of People.” Similar to her University of Chicago Laboratory Schoolmate the late Paul Butterfield, Jefferson was born in Chicago. She grew up in the 1950s and early 1960s attending private schools, socializing with her peers at Jack and Jill club functions, traveling to Interlochen summer arts camp in northern Michigan, and spending leisure time on the family yacht. While enjoying a comfortable upbringing, Jefferson was always on guard to contain herself, knowing full well that “Negro privilege had to be circumspect: impeccable but not arrogant; confident yet obliging; dignified, not intrusive.”

Indeed, in her youth, Jefferson was constantly reminded of the imperative to know her place, of the strictures of what she terms the “fortress” of segregation. She listened with chagrin as her mother recounted an incident of the family’s white laundryman snubbing her in a chance encounter at Sears; another time her father, a respected doctor and head of pediatrics at what was America’s oldest black hospital, Provident, was rousted by the cops in his own neighborhood on the way home from the office and accused of carrying illegal drugs in his medical bag. Jefferson herself was often teased by white playmates as a child, subjected to the blithe disregard of teachers who taught literature and songs tainted with racist sentiment, however oblique, and inundated with representations of dominant, which is to say white, culture in everyday encounters with the so-called mainstream print and broadcast media. At the same time, Jefferson’s privileged status required maintaining psychological and physical distance from blacks of lower socioeconomic status, whose failures the more elite segment, including her own parents, denigrated as “[making] it hard for the rest of us.”

Jefferson terms being caught in the fault line between the social imaginaries of white and black in American society as the condition of “the third race.” As she writes,

“We cared for our people — we loved our people but we refused to be held back by the lower element. We did not love white people, we did not care for them, but we envied them and sometimes we feared and hated them.”

And yet there was also the realization that much of Jefferson’s social cues, in terms of lifestyle and expectations, came from white upper-middle-class society. At one point, she observes feeling that she had more in common with white peers at her exclusive private school than the greatly less-advantaged majority of blacks with whom she rarely if ever interacted. She notes thinking at one point that Paul Butterfield, with his immersion in South Side Chicago blues, was more closely in touch with what from a mainstream perspective was considered “authentic” black culture than she was. Jefferson does not comment on it, but that appropriation of blackness is yet another white construction as an iteration of the Noble Savage in Western culture. It can be seen during the period of Jefferson’s childhood, for example, in Jack Kerouac’s description in On the Road of the Denver nightclub hot jazz combo in which “the big Negro bullneck drummer” attacks his kit with a primordial “Boom, kick…kicking his drums down the cellar and rolling the beat upstairs with his murderous sticks, rattlety-boom!” And then there is the more “superficial” hipster adoption of it in Norman Mailer’s notorious 1957 Dissent magazine essay, “The White Negro.”

The word “Negro,” capitalized, is consciously and rigorously used by Jefferson throughout most of the book, abandoned only in the final sections, when moving from the years of her upbringing to the beginning of her professional life in the 1970s as a reporter for Newsweek, where she replaces it with “black.” (She uses “African American” only once as a self-identifying term in recounting an episode from the 1990s of buying hair-care products in New York’s West Village.) “‘Negro,’“ she writes, is “a word of wonders, glorious and terrible.” Its various connotations have shifted over time and, depending on context, have informed her understanding of race and its construction, politically, socially, culturally, and, of course, personally.

From this semiotic ground zero, Jefferson launches her chronicle of Negroland. The book is subtitled “A Memoir,” though in truth it is really more what social researchers term an autoethnography (a less marketable term to be sure), which describes a form of self-reflective writing that places an individual’s experience within a wider cultural, political, and social context. With her many years as an astute cultural critic, Jefferson cannot help but take a broader view of her life within the larger narrative of American social history. The first few sections of the book trace the emergence of the black elite back to its origins in the antebellum plantation slave system, through the 19th-century stirrings and spread of the abolitionist movement, and on into modern civil rights and black pride. The capsule profiles of important figures in that story, some well known and others less so, constitute a useful survey of social history in and of themselves.

Woven throughout the book are also meditations at the intersections of race, class, and, especially, gender. Trenchant in this latter regard are the taxonomies of skin color, grades of hair, and the shapes and sizes of noses and derrieres as markers of female beauty. (Baby definitely don’t “got back” in 1950s Negroland.) Also noteworthy is the suspicion with which many black women in the 1970s and 1980s viewed second-wave feminism as a middle-class white woman’s thing. In response to that notion, Jefferson quotes Florynce Kennedy:

“When black women tell me feminism is a white woman’s thing, I tell them: you’ve spent all these years, all these centuries, imitating every bad idea white women came up with—about their hair, their makeup, their clothes, their duties to their men. And now, they finally come up with a good idea — feminism — and you decide you don’t want anything to do with it! ” (italics original)

Another resonant section pertains to relations and other acquaintances who crossed the color line and became estranged from family and friends, sometimes for a lifetime. One is a relative identified only by his initials J.E., presumably to protect his legacy for two ostensibly white sons who have never been told of their racial heritage. Another is a cousin, Lillian, who lived her life as a fair-skinned Negro and passed for convenience when patronizing white-only shops and restaurants. She also served as a go-between for passers and non-passers on the Jefferson side of the family. Another interesting case is Jefferson’s great-uncle Lucius, who after decades of passing for white as a traveling salesman “resumed his life as a Negro” upon retirement. In reading this section, I was reminded of two books Kendall and Jefferson assigned our New School class: James Weldon Johnson’s Autobiography of an Ex-Colored Man,originally published anonymously in 1912, and Nella Larsen’s Passing from 1929, both of which explore the treacherous terrain at the borders of race. Where those writers present fictional accounts, Jefferson reports on facts. I was also reminded of the times that I, a person of Mediterranean descent, have been taken for black, one of them at a party by an Africana Studies professor who kept insisting I was passing.

As with Jefferson’s previous book, the 2006 On Michael Jackson, Negroland is filled with incisive commentary and unexpected observations, all of it delivered with a sly wit and in crystalline prose.

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A version of this article was previously posted on the author’s blog, Motown Review of Art.