Scene: New York City, some­time in the sixties. Mary McCarthy, former "dark lady" of American letters, walks up to the young Susan Sontag at a party and says, icily: So I hear you're the new me. (In some accounts: the imitation me.) This exchange will become famous, though no one—least of all Sontag herself—seems to recall it actually happening.

But we like the story. Literary gossip has all the pleasures of the normal sort and something a little extra. Knowing the quips and predilections of the smart, famous, and dead brings a special thrill; they were just like us, only somehow more so. They know their roles and, in stories like this one, seem to be aware of playing them. It's almost, Michelle Dean wryly comments in Sharp, as if "intellectual life were a kind of gothic novel."

In addition, a mystique can accrue to particular circles and places—but over time, as one encounters the same anecdotes over and over, they can become tiresome. "Bloomsbury is, just now, like one of those ponds on a private estate from which all of the trout have been scooped out for the season," wrote Elizabeth Hardwick in her 1973 essay " Bloomsbury and Virginia Woolf": "The period, the letters, the houses, the love affairs, the blood lines: these are private anecdotes one is happy enough to meet once or twice but not again and again."

Nowadays it's Hardwick's own circle—the so-called "New York intellectuals"—that plays this role for us, not Bloomsbury. Hence the appeal of the McCarthy-Sontag anecdote, fished out as many times as it has been. It's a story of one bitchy intellectual accosting another at a party, a sea of intellectuals drinking hard and arguing about ideas and shoving each other around with their big personalities. In which sea there is only ever one exceptional woman at a time. Witty, beautiful, drinks too much, acid-tongued—you know the type. One retires, another appears.

In Sharp, Dean, a journalist and literary critic, recenters the New York intellectual world around its women. As her guiding theme, she takes these women's reputations as "sharp," cruel, or ruthless, linking them together by how they were talked about. The women she focuses on—Dorothy Parker, Rebecca West, Zora Neale Hurston, Hannah Arendt, Mary McCarthy, Susan Sontag, Pauline Kael, Nora Ephron, Joan Didion, Renata Adler, and Janet Malcolm—fill the book easily, and there are enough other women popping up in the background that one could imagine an entire other book with a different cast.

Dean writes perceptively, if sometimes in a slightly detached way, about these women's achievements and failures, the sorts of things they wished they could have done, and their blind spots (notably, for West and Arendt, blind spots related to racism). Occasionally, Dean withholds her own judgment a little too much; it's hard to read about all these opinionated women and their controversies without wanting the author to come down on one side or another.

But for the most part, Sharp is an insightful book that works well to introduce its subjects to newcomers while containing enough of Dean's analysis to be interesting to readers already familiar with them. Dean highlights some of the obscure or even a little embarrassing works by these writers. (For instance: Susan Sontag once wrote a piece for Vogue that advised cultivating optimism by assuming, among other things, "that we suffer uselessly.") While Dean carefully frees these women from their reputations for cruelty, she documents the ways in which they are part of intellectual history, linked to and in conversation with each other, not one-offs in an endless series of Dark Ladies.

Dorothy Parker, long an inspiration to many a sardonic brunette, takes her place as the first in Dean's line of women—and her ghost lingers long after she's left the page. Parker made her name through a series of, well, sharp reviews, observational pieces, light verse, and, eventually, short stories.

But it wasn't very fun being Dorothy Parker, seeing through everything, including herself. She didn't find much to celebrate in her own success. The sort of work Parker admired was being done by men like Hemingway and Fitzgerald, to whom she could pen tributes (in the former case) or good-natured parodies (in the latter) but among whom she could not assume her place as an equal. (In Hemingway's case, not only was Parker's admiration not returned, he seems to have hated her.)

Being known for being sharp means being recognized and marketed as a personality rather than an intellect. Being sharp is not the same thing as being profound or even smart; it signals a talent for observation, rather than insight or originality, and moves the kind of work these women did into the realm of natural instinct.

To some extent, that's still the case. There's Dorothy Parker, and then there's "Dorothy Parker," and they aren't really the same. If it's the latter you want, you can buy a Dorothy Parker gin; you can buy a Dorothy Parker shot glass; you can drink the gin out of the shot glass and post a picture of them on Instagram to show you, too, are sharp, sad, brown-haired, and drink irresponsibly. (Let the record show I have done all these things.) That's the image—the screwball gal. The "good sport," as Parker characterized it in one of her stories.

What Parker put into her writing was something more than this, but her hatred of her image-self didn't come from nowhere. It made her name, but put her in a prison from which she could only try to escape by attacking herself. Of all the women in the book, she is the one who wrestled the most with the double-edged nature of her own reputation; she seems to have understood her situation more clearly than the other women portrayed in Sharp understood theirs. And when reading about Parker's career, it's hard not to reach for present-day analogues—the hip websites that use women's cultural knowledge to build audiences while reserving the actual power and prestige for men, or the women who rocket to fame by selling their personalities and then burn out.

Dorothy Parker eventually condemned her work and herself, writing for a Communist publication that "the only group I have ever been affiliated with is that not especially brave little band that hid its nakedness of heart and mind under the out-of-date garment of a sense of humor." But one irony of Parker's intense self-hatred, as teased out by Dean, is that of all the women in this book, she is probably the one most read and remembered today. Not because the other women are obscure—they aren't. But while Parker might not have written the work she wanted to write—and might not have had much feeling for what she wanted to write beyond self-reproach—she captured a way of seeing and understanding the world, a bruised romanticism. It's that quality—not the acid tongue or the good sport—that's kept us reading her.

But the problem of being known as a personality as much as a writer remained for her successors. "Everything is copy," a young Nora Ephron's mother once told her, and she took it to heart, writing essays about humiliating experiences, a novel about her unfaithful husband. She struggled with the women's movement, wanting to express both solidarity and criticism when it came to magazines like Cosmopolitan or somewhat schlocky novels by prominent feminists, feeling trapped by the demands of feminism and resentful of the mockery of men. ("Like all things about liberation," she wrote, "sisterhood is difficult.") For Ephron, selling your personality and your story was a way of avoiding being trapped, rather than the trap it became for Parker.

If the women in Dean's book are incorrectly linked under the category of sharp, they might be better understood via a phrase coined by Hannah Arendt: "conscious pariah." The women in this book were many things—brilliant, difficult, successful, frequently wrong—but they were all outsiders. (Often literally: Arendt, Adler, and Malcolm were all immigrants.) "A conscious pariah knows she is different," Dean writes, "and knows she may never, at least in the eyes of others, properly escape it. But she is also aware of what her individuality gives her."

Fittingly, then, it's Hannah Arendt who succeeds most at climbing out of the shadow cast by the Dark Lady. Though Arendt would also be reproached for her lack of feeling—most sensationally, when she covered the trial of Adolf Eichmann for the New Yorker—she does not have the thwarted quality that most of the other women in the book have. She might have been snidely dismissed by some of her male peers, but she accomplished the work she set out to do and does not seem to have been troubled greatly by the opinions of others. And her warm friendship with Mary McCarthy belies the idea that these women could only be each other's rivals.

None of the women in this book had it easy. Some of them ended up in careers that were not the ones they really wanted: Susan Sontag tried to escape the essay-writing life to make films, which flopped. Before that, she'd tried her hand at novel-writing and failed there too. Mary McCarthy, much like Parker, tried to put her writing to the service of political causes, without much success. Janet Malcolm didn't really want to be a journalist at all but found herself working as one after the untimely death of her husband. Others ran up against hard walls: Renata Adler would end her journalism career by biting one hand too many. Pauline Kael—again rather like Dorothy Parker—would be driven by self-hatred as much as by ambition. Rebecca West had to watch herself age from young firebrand into irrelevance. Zora Neale Hurston would never in her lifetime, and arguably not even after, get the respect she deserved.

It wasn't easy being any of these women. But in refusing to let things be easier, what a gift they gave to all of us.