My snobbery began in third grade, at Pioneer Valley Montessori School. That was when I ceased writing my name as “Mark” in the upper-right corners of my papers and instead began writing “Mark the Great.” I remember precisely why I donned this new epithet: It was because my teacher that year, a young novice named Lisa, hated me.

Lisa practically seethed in my presence. One reason was that I talked back. Not in a rude way, I think, but in an insistent and articulate way. I had a very wide vocabulary for an 8-year-old boy, I loved argument, and I was deeply suspicious of much of the school’s Montessori pedagogy. Time lines, for example: Why were we supposed to learn history by unscrolling a piece of paper, lying on the floor, and using pencils to draw a long line with hash marks representing various dates in, say, American history? I would ask Lisa questions like “Wouldn’t it make more sense to just read a history book?” And Lisa, fresh from her Montessori certification, flush with the convert’s zeal, hated that kind of impudence.

So she would yell at me, or tell me to go away, or—on one memorable occasion—inform me that none of my classmates liked me. In that instance, she proved her point by calling for quiet in the classroom and then demanding, “Anyone who likes Mark Oppenheimer, raise your hand!” When my stunned classmates failed to raise their hands, she looked at me as if to say, “See?”

So in this toxic and topsy-turvy environment, where my gifts were liabilities, my survival strategy was to valorize my skills—to become snobbish about them. Lisa was determined to show me I was nothing, so I decided that I was everything, and that the ability she hated most in me was the one I could be proudest of. I became Mark the Great! And I fear that it was then, in third and fourth grade, that I began to see less articulate classmates as inferior.

What I had always perceived as just the natural variegation of young people—I was a good talker, some children were good at sports, others were good at making friends—became a hierarchy of abilities, with me at the top. Nothing was more important than being good with words; of slightly lower value were other kinds of academic gifts, such as being good with numbers (Eli Brandt could do long division in third grade); lower still was being a gifted athlete; a bit lower, but still admirable, was owning an Atari video-game system, as a sweet, pudgy boy named Michael did; below that was mere unearned popularity.

I had, in fact, turned the normal childhood hierarchy on its head, persuading myself that the cool kids were worthless, that video games mattered less than math skills, and that nothing was cooler than being able to talk like an adult. The wisenheimer was king!

So far, this was a schoolyard, junior-varsity Lord of the Flies version of snobbery. It did not intersect at all with the class-based snobbery, present in every society, that the English writer P.N. Furbank calls “the unholy pleasure.” My pecking order had nothing to do with money, breeding, education, or ethnicity. It was fairly benign, and it would have appeared more so with time: An adult who thinks that being smart is the most important thing is—so long as he keeps his opinions within his household and the domus of close friends and relatives—not a terrible guy. In a society that worships sports, money, and power, he’s even a bit countercultural.

It is not unusual for snobberies to begin as self-defense—they are almost necessarily the province of minority groups worried that they might any day be vanquished: The landed English were surrounded by the peasants, the educated Ivy Leaguers by hoi polloi. Beneath the airs of superiority one can quickly discern the grounding of insecurity. After all, if the war comes, sheer numbers dictate that the snobs will lose. And given how much of the snobs’ privilege is unearned, their snobberies can also be seen as strategies of obfuscation, enabling them not to see the important injustices that their cherished order perpetrates. Consider the banker who refuses to hire people with working-class accents: Because they sound as if they lack money, he deems them unworthy of making money.

But self-protective armor can be used in the offensive, too; judgment nearly always turns judgmental. Nobody likes to relinquish a snobbery, even when it becomes safe to venture forth without it. When I left the Montessori school for New North Community School, a big, ugly, but very happy public school where I was to spend fifth and sixth grades, I was quickly welcomed into the culture of my new classroom and immediately found a raft of friends: buck-toothed Craig Nicholson; Jheri-curled Steven Barnes; hapless, cow-licked Billy Burke; athletic, preppy, Esprit-wearing Tammy Duchesne. And yet it was among those decent, generous, accepting souls that my snobberies multiplied.

By the time I graduated from New North, I was preening about more than my verbal ability. I had become, in my mind, an aristocrat, my superiority evident in my bloodlines, my parents’ education, my clothes, my pronunciation of words, my taste in reading, and even my haircut (I had a goofy bowl cut, which I deemed nobler than my classmates’ buzz cuts or proto-Kid ‘n Play creations). Even though I was happier than before, I was, like all 10- or 11-year-olds, still very much unbalanced, unsure of where to plant my feet in the world. So I looked all around, and steadied myself with fragile certainties that whatever I did, it made me better than those around me.

Thank goodness that my friends and schoolmates must have been busy with their own ridiculous, desperate self-preserving strategies, so they didn’t perceive how ridiculous I had become. And thus we could all stay friends. But I think that the smug beliefs I was coming to hold exacted a toll more lasting and more damaging than Tammy’s early-adolescent obsession with fashion (“My clothes make me better,” she seemed to be saying), or Demond Williams’ wannabe-Casanova strutting (“The ladies know that I am the man“). My more encompassing snobbery became a habit of mind, difficult to shake, my indwelling friend and foe to this day.

That’s why it is very difficult to be a true snob before the age of 9 or 10. The infant or toddler is by nature a solipsist, concerned only with satisfying certain immediate wants. The young child of, say, 3 or 4 years old begins to look up to older children, and to desire their acceptance, and the slightly older boy or girl, newly able to think ahead and coming to possess some social intelligence (and cunning), may begin to recognize that a given skirt, or a facility with soccer, will ease one’s way—but this is a very utilitarian plotting, along the lines of, “If I wear that skirt, she will like me.” The next stage, the one I reached in third and fourth grade but began to perfect in fifth, is the abstraction of these principles, the infusion of them with moral judgment—the decision, for example, that using big words makes me a better person even if there is no obvious reward for doing so, or perhaps because there is no obvious reward for doing so. A child must reach a certain age before he can decide that rejection is the proof of his superiority.

But once a child can reason that way, the possibilities for new snobberies are endless. And, fortunately for that child, American popular culture is happy to supply him with ideas. For example, I knew that my parents valued the reading of the Sunday New York Times. I knew this because they went out of their way to acquire this publication, walking to the Food Bag convenience store at the corner of Bronson Terrace and Dickinson Street to purchase this newspaper. I knew that most of our neighbors contented themselves with the Sunday Republican, the local newspaper of Springfield, Mass. Even at age 10, I must have recognized that the Times had more difficult content. It was not hard to infer that consuming the Sunday Times was some marker of intellectual accomplishment, and to further assume that whatever was contained in that thicket of words and images was a small sampling of the heroic life.

I fixed on the New York Times Magazine, in particular the lush advertising spreads that Ralph Lauren seemed to purchase nearly every week, in the expensive space before the table of contents. They were veritable guidebooks to a leisured, monied, Gentile fantasy world, where the country squires never went bald, only silver; where their wives were nowhere to be seen; where their daughters were honey-blond, freckled, and happy to walk the Irish setter; and where their sons, home from college, never looked better than with hair tousled, clothes rumpled, and leather satchels loosely slung. I fetishized these lovely, landed people.

From those advertisements, I learned the preppy style. I began to see it all around me. I saw it on certain pages of the L.L. Bean catalog, which we received every month or so, and I saw it in the window of the Brooks Brothers store at Westfarms Mall in Connecticut, the mall where my mother took me shopping when she needed a skirt for a special occasion, when the shops at Enfield and Eastfield malls just would not do.

More important, I began to notice where that style was absent. Our street, Bronson Terrace, a slightly upper-middle-class street in the Forest Park section of Springfield, was the northern border of a little community within a community, where the houses were single-family and the lawns were well-tended. There were two streets to the south that looked like ours, more or less, Texel and Elwood drives. Then the neighborhood was squeezed to its termination at the confluence of Dickinson and Trafton, two arterial roads that met with finality at the tip of a triangle. On my street and those parallel streets to the south, one might spot a Polo shirt, or a pair of Blucher moccasins. But on all the streets to the north, beginning with Olmsted, just around the block, the uniform ran to acid-washed jeans, Flashdance-inspired leggings, hair-sprayed big-hair, and Reebok aerobics shoes for the girls, Nike basketball high-tops for the boys.

And with the innocent wisdom of a child, untroubled by classist inferences, I saw what was obvious. To the north, in the land of big hair and acid-washing (also the land of the revving Z-28 hot-rod in the driveway, the three-family house, the unkempt lawn, the teenagers loitering in the middle of the school day), there was more dirt, and noise, and chaos. Kids were territorial: There was a group of junior-high girls at the eastern end of Olmsted who would demand, whenever I walked by their row of houses, “Where the fuck do you think you’re going?”

On my street, people dressed in the Ralph Lauren spirit, even if they could not afford his clothes exactly; on Olmsted, nobody dressed that way. I saw the correlation; it was quite apparent; it was undeniable. There was a uniform of civility and decency, and the people who wore it were likelier to be nice to me, and to one another. They were better.

At school, the student body was racially divided into thirds—black, Hispanic, white—and the minorities cared much more about their appearance than whites did. The white boys, in particular, were mostly indifferent, and it was a girl, Tammy Duchesne, who was my peer in sartorial awareness. She wore two brands exclusively, Benetton and Esprit. It took me some time to sort out the class connotations of these brands, but eventually I figured out, if not in an articulable way, that these labels sent the message that she could keep up with trends—these brands were everywhere, Benetton with its ubiquitous ads and Esprit with a store in every mall. The clothes were not cheap; one saw them on white girls only, and white girls from the better families (Bronson, not Olmsted). And yet I perceived that there was something subtly déclassé about Benetton and Esprit, precisely because they were so of the moment. The Ralph Lauren ads, by contrast, announced the clothes’ archaism; even as they defined a kind of trendiness, they practiced a denial about that trendiness. Like all good totems of snobbery, they were for a defiant minority, definitely not for the majority.

Inspired by Alex P. Keaton, the preppy conservative teenager on the television show Family Ties (another nerd who found dignity in snobbery), I one day brought a briefcase to school, an old clunker my father had abandoned in our basement. “It’s for my important papers,” I told Mrs. Britt, our school-bus driver. But the stares I got in the hallways were too much, and I abandoned that project immediately—one more bit of evidence that I was not a true eccentric. My sense of superiority was too close to its roots of inferiority; I could not choose to stick out on purpose. Where difference was unavoidable—I could never have pulled off Air Jordans and acid-washed jeans—I made a virtue of my difference. But I soon was forced to admit that I couldn’t make a briefcase cool.

I began to draw conclusions from things that my mother had told me about my father’s childhood. I construed every fact as romantically as possible. My grandfather married six times and died young? Why then he was a bonvivant! I preferred the most handsome photograph of him, one in which he is posed with a briefcase and wearing a plaid waistcoat under his suit, the very picture of the amiable, world-traveling Jules Verne character. He was, after all, in the rather mysterious and alluring import-export business. And his forebears—why, two of them, his father and great-uncle, had their very own entries in Western Pennsylvanians, a volume so ludicrous I would not believe it existed, were it not for its permanent residence on my parents’ living-room bookshelf, with sewn bindings and two black covers, the title embossed on the cover in gold, the pages of heavy stock bearing elegant black-and-white photographs. The mere existence of “Who’s Who” volumes like this one, edited by one Charles Alexander Rook and published in 1923, hints at the tragedy of the snob, which is that he needs to think he is grand just to think he is worthwhile.

But then plain, denuded truth is not much fun, is it? Life without family coats of arms is much less colorful. Not only for the person who lives without family mythology, but for her friends and loved ones, too. It is interesting, after all, to have a friend who says she is descended from a long line of pathbreaking feminists; one does not want to fact-check her stories; one does not want to apply any Google scrutiny. It is delightful to marry somebody whose grandmother says that her grandmother was a baroness, and it is all the more delightful if her stories seem just barely plausible. I imagine Australians sit around drinking their Foster’s, competing to see whose great-great-grandparents committed the more heinous crimes to get exiled to the penal colony.

I have long wondered how to make sense of snobbery’s many faces. Wherever snobbery can be found, it is evidence of insecurity, even emotional poverty; and yet it is frequently one of life’s great pleasures. Consider two favorite books of my early teenage years, both of which I was to discover have wide followings. Their titles live in the lingua franca of Anglo-American snobbery, and when you meet someone else who loves one of these books, there is immediately a lot of knowing, no-need-to-speak smiling and nodding.

The first book is The Official Preppy Handbook, by Lisa Birnbach. I found this 1980 book around 1989, I think the summer after my first year at Loomis, a reasonably well-regarded prep school in northern Connecticut, one that now might be described as producing good food writers: Corby Kummer of the Atlantic magazine and Frank Bruni, past restaurant critic for the New York Times, are both alumni. In my first year at Loomis, I had just begun to make sense of the welter of different fashions, codes, and shibboleths that constitute boarding-school style (it did not help that I was a day student, so definitely second-class). For example, I had figured out that there was something classy about leaving old lift tickets from ski slopes dangling from the tab of one’s parka zipper. I had quickly mastered that a certain amount of fraying of the cuffs connoted elegance. There was a premium on the appearance of age: nothing too shiny. And there was something special, I gathered, about wearing clothes bearing the names of prep schools other than one’s own: It suggested that your friends, whose shirts you gathered off the floor of one Maine cabin or another, also attended prep schools.

But Miss Birnbach, with the zeal of an outsider—she was Jewish, and attended a day school outside New York—had the wonderful gumption to spell out which schools were preppy, which not; which vacation locales were exclusive, which were drearily democratic; which clothes could be worn, which really ought not. One chapter explained the differing connotations of loafers and top-siders. And she had figured out the mysterious principles behind certain seemingly arbitrary, but quite undeniable, pecking orders. For example, in sport, the smaller the ball, the higher-class the sport. Hence squash outranks tennis, lacrosse outranks football. You can quibble with the examples, but Birnbach had a genius for making explicit and comprehensible what otherwise, especially to the neophyte, could seem a bewildering set of unwritten laws.

I suspect that Birnbach was deeply conflicted about prepdom, and probably hated some of the preppiest people she knew, and thus was eager to describe them as the superficial twits they were. She smartly chose to use humor as her weapon, and I think she also found a certain refuge herself in the snobbery she was describing. She thus offered a witty, fairly generous-spirited version of preppy snobbery: She was aware of its foibles but seduced by them nonetheless. And what she wrote was, after all, a handbook; it allowed anyone who read it, like 14-year-old me, to walk a little more confidently in the world it so cleanly dissected. In fact, after acquiring The Official Preppy Handbook, I decided that I was in possession of knowledge that many of my richer, more truly preppy classmates lacked. They didn’t seem to know which three schools were known collectively as “St. Grottlesex,” but I did—so who was the real insider?

At about the same age, my friend Derek’s father, a minister with a mischievous sense of humor who himself liked to observe, and indulge in, various benign snobberies, took me and Derek into a shopping-mall Waldenbooks and bought for me a copy of Paul Fussell’s Class, a crueler, funnier, and more intellectually penetrating improvement on The Official Preppy Handbook. Class is different in that Fussell, by training a literary critic, is concerned not just with the upper class but also with the various lower classes (“upper middles,” “upper proles,” “low proles,” and the like). He wants to describe the wardrobes and decors, and plumb the psyches and neuroses, of all Americans. What in Birnbach is always good fun—after all, whether mocking or exalting she is always writing about privileged white people—in Fussell is often like vivisection, performed not on pampered purebreds but on hapless, unwilling mutts.

What is amazing about Fussell is his totally self-confident prescriptivism: He writes omnisciently, as if he were Nabokov pinning butterflies. According to Fussell, there are three categories of American: upper, middle, and prole. Within each of those categories, there are three subcategories. The people at the top and the bottom can be quite similar, in that one never sees them (the upper-most uppers are at the ends of very long driveways, the lowest lowers are in homeless shelters or in prisons), in that they can be quite stupid, and in that they think very little about class. Those to be despised are the striving middles. (One is put in mind of the famous line about patrician New York mayor John Lindsay, that he liked only the very rich and the very poor.) A sampling of Fussell’s pronouncements: “Billiards has status only if a separate room, rather large, is devoted to it exclusively. Billiard tables which, once a cover is set into place, become the family dining table are high-prole.” “One way to learn which flowers are vulgar is to notice the varieties favored on Sunday-morning TV religious programs like Rex Humbard’s or Robert Schuller’s.” “If you drink martinis after dinner, you are a prole.”

Fussell, perhaps terrified of the assuredness of the taxonomy he’s created, adds another category: Category X. “Some Xs are intellectuals,” Fussell writes, “but a lot are not: they are actors, musicians, sports stars, ‘celebrities,’ well-to-do former hippies, confirmed residers abroad, and the more gifted journalists, those whose by-lines intelligent readers recognize with pleasant anticipation.” In other words, Fussell and his friends. His X category is presaged by an exchange between Martin Amis’ brother Louis and their father, the novelist Kingsley Amis, recounted in Martin’s memoir, Experience: “—Dad. —Yes. —What class are we? —We aren’t. We don’t buy that stuff. —Then what are we? —We’re outside all that. We’re the intelligentsia.”

It’s to Fussell’s credit that, like the adult Martin Amis, he realizes this Category X business is sustained by wishful thinking. Nobody is outside the class system, and in fact Category X people are a cliché unto themselves: “L.L. Bean and Lands’ End are the main costumers for X people,” Fussell writes, intentionally undermining his contention that Category X is any sort of meaningful escape hatch.

After all, as Fussell writes elsewhere in his book, “If you find an American who feels entirely class secure, stuff and exhibit him. He’s a rare specimen.” So even though I know that Fussell does not quite mean what he writes, that he is laughing at all of us, I also know that whenever I see someone with a Mini Cooper convertible—an expensive car I truly covet—I tame the beast of envy by reminding myself that, according to Fussell, my 1999 Honda actually has more snob appeal.

The problem, of course, is that after a while the snobbery game, like any game played consistently over many years, becomes quite serious. Just as there are no true “recreational” golfers, there is after a while no such thing as a recreational snob. The judgmentalism moves to the fore, and the snob really begins to see people as mere butterflies, objects for classification. Fussell is particularly insidious, because he has thought of everything; his class-based outlook is a satisfyingly complete system, like Marxism, or Christianity. Once you have read Class it becomes hard not to evaluate a friend’s living room according to Fussell’s simple, handy point system: “Hardwood floor: Add 4 … Vinyl floor: Subtract 6 … Threadbare rug or carpet: Add 8 (each) … Ceiling ten feet high, or higher: Add 6 … Any work of art depicting cowboys: Subtract 3….” When my wife bought a swing set for our daughters to use in our backyard, I found myself asking what Paul Fussell would have to say about it.

Looking back, I suspect that this tendency was particularly poisonous to my dating life. How many eligible women, I wonder, did I dismiss with prejudice because they had school stickers in the back windows of their car? (Fussell: “You can drive all over Europe without once seeing a rear-window sticker reading christ church or université de paris.”) Or because they mourned a relative who had recently “passed away”? (Only middles say “passed away”—or, Fussell would add if he were writing today, the barbarism “passed,” made popular by the TV “psychic” John Edward; the upper says “died,” the prole, “taken to Jesus.”) One time a woman broke my class-o-meter on our first date by saying “rather” with a broad “a,” as “rahh-ther”: It first struck me as a bit of middlebrow pretension; then I remembered that a true Boston Brahmin I once knew, boarding-school- and Yale-educated, had said the word that way; but then I remembered that she always struck me as pretentious herself, surprisingly considering how class-secure she should have felt; and before I could figure it all out I had lost enthusiasm for the dinner, and the company.

Yes, because snobbery is ultimately a dysfunction, and if my daughters were to lose potential close friendships, and someday lovers or partners, because of the trivia they imbibed, via their father, from The Official Preppy Handbook and Class, then I would have a lot to answer for. And once you learn snobbery, it is very hard to unlearn. They would be wrecked for life, like me.

Also, of course, snobbery is immoral. It is unkind, and frequently vicious, and built upon lies about what other people are really like.

And yet I am not convinced that I can give up snobbery so quickly. Because as much as it could harm my daughters, it could also make them Oppenheimers. For after all, snobbery is one of the great midwives of human closeness. Almost nothing I can think of unites two people better than shared snobberies. I never feel more married to my wife than when we enter another couple’s house for the first time and, on seeing that the television is a bit too large, or too prominently placed in the front room, look at one another and—well, I was going to say “arch out eyebrows,” but of course we do not even need to do that. The mere look, the meeting of the eyes, does it all.

When she asks me to describe a town that I have seen on my travels, and I can use the shorthand of, “Well, you know—a lot of above-ground swimming pools,” I am grateful that we are united in our dim view of above-ground swimming pools. Call this a shared aesthetic, call it a shared sensibility, but please do not lie: It is also a shared snobbery. And one reason that we feel so much that we belong together is that while we share much more, we share at least that much.

I cannot bring myself to want my daughters cut off from that aspect of Oppenheimerness. I sometimes ask myself if there are those who truly think that all people are equal, who have no problem not saying anything at all if they can’t say anything nice. I think I have met people like that; from what I can tell, there seem to be some in the Midwest. They go through life not judging, not condescending. I suppose they are close to God. They certainly have an easier time making friends. But I think that what they call friendship is what I would call mere fellowship.

I cannot imagine closeness without some sort of secret handshake. I may be one of those people P.N. Furbank had in mind when he wrote that “if one person speaks to another about ‘class’ he or she is ipso facto creating a tacit understanding with the other.” I do wonder if I can ever change; I cannot decide if I even want to. I think the best I can hope for is to see my snobbery as a set of neutral, amoral preferences, most of them arbitrarily chosen. The art critic Dave Hickey has written that good taste is just the residue of someone else’s privilege, and I have to admit that’s right. God—the universe—the perfect good—whatever you want to call the arbiter of moral truth—does not care whether my floors are parquet or covered by wall-to-wall carpeting. That I do care is a fact about me, best confronted and managed. It is not to be exalted, but it cannot be honestly denied.

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