When Helen Gurley Brown died in 2012 at age 90—and was cremated in a Pucci dress—she had spent her career giving voice to desires previously off-limits in public. She had transformed Cosmopolitan from a dying general-interest magazine into a widely read monthly celebrating women’s pursuit of sex; for three decades, and during successive feminist waves, the magazine dominated the market for women’s publications. She had published thousands of articles about overcoming hang-ups and achieving orgasms in prose she made “baby simple” with words like “pippy-poo.” For the women who read her regularly, her work offered necessary encouragement. “There are a lot of women out there who need help and they are $100 and 50 miles away from a psychiatrist, and what we are trying to do is absolve them of guilt by letting them know they’re not alone,” Brown told The New York Times Magazine in 1974, nine years after she took over Cosmo.

The reaction she provoked among feminists and intellectuals was often closer to horror. “Her market seems to be composed of people who ordinarily set eyes on a book only when Johnny Carson holds one up,” wrote Joan Didion in a 1965 profile. In the view of Nora Ephron, “She is demonstrating, rather forcefully, that there are well over a million American women who are willing to spend sixty cents to read not about politics, not about the female-liberation movement, not about the war in Vietnam, but merely about how to get a man.” The feminist group New York Radical Women attacked her as “Aunt Tom of the Month” in the first issue of their broadside, Notes From the First Year. Kate Millett occupied her office and demanded that she attend a consciousness-raising meeting. Many saw her as toxic, elevating man-­pleasing above all else. She was widely scorned for avoiding race or for dealing with it clumsily in articles like “What It Means to Be a Negro Girl” and “The Black Man Turns Me On.”

Two new biographies attempt to redeem Brown: Not Pretty Enough by Gerri Hirshey and Enter Helen by Brooke Hauser. Both praise her tenacity and vision at the helm of Cosmopolitan. For Hauser, Brown’s work as an editor and writer is foremost about independence, achieved by a woman who “was a much more serious person than she presented herself to be.” “She was the unlikeliest of sirens,” Hirshey writes, with a “sincere and underrated feminism.” Yet Brown’s beliefs were often just as retrograde as the ones she claimed to fight. Why, then, is she still appealing? (Two new biographies?) These books point to an answer.

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Brown was born, as she would later describe it, “ordinary, hillbilly and poor” in a small village in the Ozarks in 1922. Her father, Ira, was an aspiring politician; her mother, Cleo, was a melancholy housewife with, Brown would say, “as much insight as a waffle.” They lived mostly comfortably until 1932, when Ira jumped into a moving elevator—rumor had it he was chasing a pretty girl—and was crushed to death.

“My shrink says that, given the set of problems I had growing up and as a young woman, it’s quite astonishing I’m not locked away in a mossy little cell somewhere,” Brown would later write in one of her nine confessional advice books. The struggles of her childhood—and her own success in spite of them—became the source material for her writing and for her conception of the insecure, shy, and eager “Cosmo Girl” that her magazine would target. Unable to support Helen and her sister Mary, Cleo drove them across the country to look for an ex-boyfriend she hoped she could marry for stability. The family finally settled for a happy while in California. Then Mary was afflicted with polio and left paralyzed; Helen hoped to attend college but could afford only a single semester. She worked 17 different secretarial jobs before she was 26, then began to find success in Los Angeles as a copywriter.

Brown offered two contradictory accounts about her ascent into the realm of magazine publishing. As Jennifer Scanlon shows in her incisive 2009 biography Bad Girls Go Everywhere, Brown aspired to be a magazine writer during her copywriting years. Throughout the late 1950s and ’60s, she submitted articles unsuccessfully to magazines like Glamour and Esquire. In one called “How to Have an Affair and Live,” she set out rules for married men who wanted to be involved with single women. In another, she anticipated the frugal advice she would offer in her books (not to mention the current obsession with Marie Kondo and “sparking joy” through housecleaning): “Throw out what’s really wrong and makes you unhappy every time you wear it. Keep what’s good.”

In her books and, later, in the pages of Cosmopolitan, Brown routinely stressed the importance of career ambitions for women. “A job can be your love, your happy pill, your means of finding out who you are and what you can do, your playpen, your family,” she wrote in Sex and the Single Girl, her 1962 guide for the erotically curious woman, which sold 2 million copies in three weeks and made her famous. She promoted office work as a panacea—for lust (offices were full of men), money problems (“Nobody likes a poor girl”), and low self-confidence (“Whether their job is good or bad, women in offices never have to search for their identity and wonder who they are”).

Yet she regularly claimed that she had never wanted to be more than a secretary. In the version Brown often related of her own success, she didn’t consider writing a book until her marriage at age 37 to David Brown, a Hollywood producer and former Cosmopolitan editor. He encouraged her to do so after finding letters she had written to a former lover about her romantic adventures. “My brilliant husband said, ‘Why don’t you write about being single? You were like no other single girl I ever knew,’” she later recalled. He also suggested that she start her own publication after noticing the fan mail she received for her book. She wrote a proposal for Femme, a publication “for women who like men [and] for women who like themselves,” but it was her husband who negotiated with Hearst to allow her to take over Cosmopolitan in 1965. “Helen was cowering in a corner somewhere,” David Brown wrote in his memoir, Let Me Entertain You. “She had never edited a magazine. I don’t think I had ever seen her read one.” Helen would joke: “In a sense I’m a product of his imagination.”

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So which one was she: the ambitious careerist or the passive wife? Who, deep down, was the real Helen Gurley Brown? This question drives journalist Gerri Hirshey’s biography. Brown was one of the most visible figures of her generation. She was also “a deeply private woman who knew the comfort and safety conferred by genteel dissembling and camouflage.” Few knew of her penny-pinching anxieties concerning money or her worries about her appearance; the death of her stepson from AIDS was kept hidden from the press. Brown was a “spewer” on the page, writing openly about her cosmetic surgeries, sex life, daily activities, and life at home cooking for David. But “over and over,” Hirshey writes, “I heard a version of this disclaimer from her friends: ‘I adored her, but I can’t say I really knew her.’”

Hirshey’s book is detailed and thorough, drawing on Brown’s archives at Smith College and other unpublished papers. She prints glowing quotes from friends like Joan Rivers, Liz Smith, and Barbara Walters. “Helen’s whole life is this monument to artifice, yet her friendship is very real,” says Liz Smith. We learn about the men who inspired the portraits in Sex and the Single Girl, including a married lawyer who read her Ralph Waldo Emerson’s “Self-Reliance” and an anti-Semitic movie-studio executive who forbade her from seeing her Jewish friends. Hirshey describes Brown’s many time in group therapy with the therapist Charles Cooke, who often urged patients to “acknowledge the pleasure value of sex.”

At Cosmopolitan, Brown decorated her office with “pink lights, pillows, candles, kitty cat knickknacks and needle­point,” and refused to publish downbeat articles. Instead, the magazine was defined from the first by the cheery promise of self-improvement. In her monthly letter to readers, “Step Into My Parlor,” she introduced herself as a kind of older sister dishing out guidance to a clueless but willing younger woman. “You’re a grown-up girl, interested in whatever can give you a richer, more exciting fun-filled, friend-filled, man-loved kind of life!” Her articles mixed confession with advice: “Things I’ll Never Do With a Man Again,” “How to Make a Small Bosom Amount to Something.” (When The Harvard Lampoon parodied the magazine in 1972, one of the fake headlines Brown objected to was “10 Ways to Decorate Your Uterine Wall.”) But despite her immediate professional success, she faced constant sexism from her colleagues at Hearst. She wasn’t invited to the company’s 50th-anniversary party. “It’s strictly a stag affair,” Hearst’s president told her.

Hirshey makes clear that she’s not interested in what Helen Gurley Brown meant for women or in larger questions about her legacy. But her attention is so tightly focused on Brown’s personal choices that the book has the distorting effect of a magnifying mirror. The details she draws on for insight often read like middle-school gossip: Brown ate with her fingers; she’d order almost nothing for lunch and then ask question after question about her dining companion’s food. In her later years, when her mind began to degenerate, she finally allowed herself sweets and gained 30 pounds. “She looked quite different,” Hirshey writes. “The Browns’ caregivers took to hiding the cookies.”

Noting flaws is important in a biography: It reminds the reader that the subject, however illustrious, was also human. She’s not trying to answer “What Helen Gurley Brown Meant for Women” or larger questions about her legacy. But in focusing on Brown’s looks, Hirshey misses other shortcomings. She highlights Gloria Vanderbilt’s concern about Brown’s attempts to control her appearance: “Vanderbilt looked keenly at her friend, watched her push food around.” But what to make of Brown’s own description of her time dating the anti-Semite? Hirshey calls the episode “a repellent racial profiling exercise,” but quotes Brown’s own self-assessment without comment. “Was I abandoning principle with my attempted Jew discernment, forsaking not only friends but ethics?” Brown later wrote. “I was being fearfully tacky, yes, but I didn’t then or even now feel too bad about my pursuit.” Fearfully tacky? Pippy-poo!

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To better understand why Brown inspired such fascination—why so many women bought Sex and the Single Girl, why Cosmopolitan took off under her reign, and why she deserves two biographies at once—it’s best to look at her writing. While Brown’s decisions may not have been consistent, her prose was: infinitely optimistic, chatty, and easy to process. Her recommendations were sometimes wise, like her insistence on financial self-sufficiency for women, and just as often tone-deaf or bizarre, like her suggestion that one change political affiliations to please a boss. But they were always memorable. After years in advertising, she wrote sentences that could pass for slogans: “Smiles are sexy.” “Think of yourself as a star sapphire. Your apartment is your setting.” “Don’t re-tire, retread.” It could all be so simple and achievable! The overall effect is both buoyant and cloying—the promises of Dale Carnegie dressed in pink ruffles.

Of course, relying on Cosmo’s tips for self-confidence had its limits, especially when the magazine depended on reminding readers of all the problems they hoped to overcome in its ads for mascara and corrective creams. In Enter Helen, journalist Brooke Hauser astutely draws a contrast between Cosmo and the contemporaneous and explicitly political Ms. to highlight the failings of Brown’s approach. Both magazines addressed women who wanted to live independently but felt uncertain about how to do so. Whereas Cosmopolitan’s more working-class readership looked for practical advice, Gloria Steinem’s Ms. advocated political consciousness and large-scale campaigns against inequality. “If you want to think about Cosmo as the poison, think of us as the antidote,” Ms. staffers would say when pitching the publication to advertisers.

But the allure of Brown’s repeated promise that “Anybody can be me” comes down less to practical tips than to tone. A woman who followed her guidance à la lettre would find herself quitting smoking while asking a man to light her cigarette. Brown understood that even by following her suggestions, a woman was unlikely to actually change her figure or her job; what she could improve was the way she presented herself. While she emphasized exercise and makeup, Brown made clear that confidence came as much from willpower and drive as from any outward alteration. “What you have to do is work with the raw material you have, namely you, and never let up.” (She took this advice to every possible extreme. Here she is offering tips for writing: “If reading is your pleasure, read, but don’t expect the magic to flow from Willa Cather into you and the words to come right out of your bone marrow…. If you want to be a writer, write.”) Nora Ephron may have implored women to be the heroes of their lives and not the victims, but Brown gave them the template to do so.

This insistence on the power of confidence is what makes Brown so frustrating. On the one hand, she pushed her readers to go after what they wanted, no matter how seemingly outlandish or silly or unlikely. She maintained that women should be able to pursue a full life: a satisfying career, enjoyable sex, a loving partner (a family, too, though disdain for children comes across strongly in her writing). One of her books is called Having It All. Brown’s cheerleading allowed an immediate sense of satisfaction not always available in the trenches of activism or political change. She realized that many women probably didn’t want to wait until after the revolution, whatever it might be, to find happiness in their lives. But while she urged women to ask for everything, the change she ultimately advocated was one of attitude.

By the time Brown died, her reign at Cosmopolitan had been over for 16 years. She had embarrassed herself and Hearst by asserting that women in heterosexual relationships couldn’t get AIDS and by minimizing sexual harassment: “I have this possibly benighted idea that when a man finds you sexually attractive, he is paying you a compliment…when he doesn’t, that’s when you have to worry.” Her later books have the coherence of a bag of party confetti. “Sneezing and rice pudding are two of the best things there are,” she writes in I’m Wild Again: Snippets From My Life and a Few Brazen Thoughts. “If smells were people and had noses, they’d probably think we smell funny.”

Yet echoes of Brown’s tone remain in much of the writing geared toward women. While Ms. scrapes by as a ghost of its former self, Cosmo publishes 64 editions around the world. (The magazine’s advertising revenue was $432 million in 2013.) Mainstream women’s magazines have taken her combination of personal essays and practical advice as a template. Scanlon notes that after years of attacking Brown, Gloria Steinem also wrote a self-help book, Revolution From Within, that recalled Brown’s feel-good tips. Lena Dunham’s best-selling memoir, Not That Kind of Girl, took its inspiration from Having It All. Brown’s fingerprints are all over the confessional writing that fills sites like xoJane and Bustle, in which any problem, no matter how grave, can be redeemed by a sense of humor and an upbeat ending. (The decidedly sober tone of this season’s most popular book on women, Rebecca Traister’s All the Single Ladies, a data-filled study on single women today, seems almost a reaction to this kind of constant uplift.) There’s nothing wrong, of course, with making the most out of what one’s got. But when boosterism crowds out every other kind of writing, it leaves women with little more than the stories they tell themselves.