The XX Factor

How Hugh Hefner’s Incredibly Complicated Legacy Got Cast as Female Sexual Liberation

Holly Madison, left, described her life with Hugh Hefner as a nightmare.

Gabriel Bouys/AFP/Getty Images

At age 91, in the Holmby Hills mansion he called home, Hugh Hefner died this week, releasing the complex feelings of an international public that paid witness to his life with a mixture of admiration, titillation, and disgust.

“Thanks to Hugh Hefner our generation learn to read magazines with one hand,” a former Colombian soccer star tweeted. Barstool Sports, home to bros who love boobs and fart jokes, posted a bunch of photos of Hefner surrounded by bikini-clad white ladies, calling him an “absolute legend.” Meanwhile, GLAAD CEO Sarah Kate Ellis sent out a statement contending that Hefner “was a not a visionary” but “a misogynist who built an empire on sexualizing women”; others called him “an abuser” and “a world class creep.” One Trump fan and singer who says she’s known Hefner since she was a teenager is beseeching commentators, “please don’t trash a man with class.”

Long before Hefner died, he was already reckoning with the seemingly conflicting legacies he knew he’d leave behind. In interviews he gave in his 70s and 80s, Hefner repeatedly positioned his life’s work as a crusade against sexual repression, a force that limited the fulfillment of men and women alike. His record of philanthropy would seem to demonstrate a progressive understanding of women’s bodily autonomy: He published features that supported abortion rights years before Roe v. Wade, and his Playboy Foundation made gifts to rape crisis centers, abortion support services, and the ACLU’s Women’s Rights Project. Hefner also fought for First Amendment protections—a predictable cause for the publisher of a nudie magazine—ran some brilliant interviews, and gave money to civil-rights causes.

At the same time, Hef’s magazine explicitly trashed women who stepped outside his feminine ideal. In 1970, the magazine ran an essay on women’s rights that both patted the movement on the head and slapped it in the face: “No other recent struggle for human rights has been so frivolous and yet so earnest, so absurd and yet so justified, so obsessed on the one hand with trivia and, on the other, with the radical restructuring of male-female relationships,” it read. Internal Playboy memos at the time found Hefner declaring of feminists, “These chicks are our natural enemy.” His very first issue scolded female readers, “get back to your Ladies’ Home Companion.”

But the effects of a few articles and donations will pale in comparison to the two signature pillars of Hefner’s memory: his naked photos and his lifestyle. Hefner kicked off his new magazine at age 27 with an act of exploitation, spending $500 on the rights to an existing naked photograph of Marilyn Monroe and running it without her consent. In the decades that ensued, he earned millions off the bodies of the women in Playboy while spinning it as a win for sexual liberation. Women can and do enjoy sex, and they should be allowed to show it, Hefner argued. Fair point! But the women in Playboy, no matter how much they enjoy posing nude and reaping what minimal payment comes of it, are not doing sexy things on their own terms—they’re following the explicit instructions of the men who make and buy the magazine. When I looked at Playboy’s encyclopedic collection of 734 centerfolds earlier this month, it struck me that the bodies in the magazine functioned as both a reflection of and prescription for male desire that, by the ‘90s, Hefner and his acolytes had made into hairless, glistening, plumped-up forms into which no human could ever transform.

This monthly collection of photos of women’s vulvas and breasts, bookended by sometimes-serious journalism, is now considered something far more mainstream than porn, no matter how garish the lights. Hefner didn’t just help make the commodification of female flesh into a multimillion-dollar industry. With his bourgeois gloss and chatter about sexual freedom, he made it the topic of respectable conversation. Perhaps his most stunning rhetorical feat was convincing a certain segment of women—and men, for that matter—that women could channel power from the patriarchy if they performed sexual desirability for men.

There was also the life Hefner led, which became more absurd and piteous with every year. He left his first wife and two children in 1959, the better to make good on the promiscuous lifestyle he sold to his readers. Men since time immemorial have certainly fantasized about leaving their ho-hum desk jobs, banal home lives, and burdensome spawn to become internationally known for their material and carnal acquisitions. Hefner gave them hope that this seductive narrative did not have to be restricted to the realm of fiction. His Playboy Mansion, the site of more than one alleged sexual assault, was the ultimate man cave: a place where, regular dudes imagined, every surface was meant for sex and every woman was meant to be fucked. Take a quick scroll through Twitter today and you’ll find dozens of men asking women for nude photos “in honor of” Hefner’s memory.

By the time he stepped into reality TV with The Girls Next Door in the mid-aughts, his image had become that of a goofy, forgetful old grandpa who nevertheless apparently had sex with multiple identical-looking women on the regular. At that point, his greatest accomplishment was convincing his fans that his life was still worth fantasizing over. One of his girlfriends at the time, Holly Madison, later wrote about the house’s dreary group-sex schedule that no one seemed to enjoy, describing her time in Hefner’s company as a nightmare. He wouldn’t let her see a therapist for her depression, she wrote, and cut her off from the outside world. If Hefner truly wanted a society free from repression, his desire for personal freedom only went so far as it benefited men.

Hefner will be laid to rest in a mausoleum next to Marilyn Monroe, whose talents and beauty helped launch Hefner’s career. The spaces around Monroe’s body are in high demand; one sold for $4.6 million on eBay in 2009. In life, Monroe might never have given these men the time of day, but in death, she has no choice—with enough money, any man can buy the right to sidle up next to her for all eternity. It’s kind of gross when you think about it: What’s sexy about having your corpse decay in relative proximity to someone else’s 50-year-old remains? Of course, Hefner wouldn’t care, because it affirms his conquistadorial image. Monroe’s body, whether animated or deceased, was just another female form for the taking.