What to make of Hugh Hefner's complicated legacy

Hugh Hefner made a fortune selling sexual freedom for the 20th century in Playboy magazine. Now with his passing at age 91, everyone is trying to make sense of the man's legacy.

He defied repressive social and sexual attitudes in the 1950s by insisting that men could make martinis, talk about jazz, and want women. And women in the pages of Playboy could have sophisticated interests and pursuits, including sexual expression.

That was revolutionary for 1950s America, but it's practically quaint compared to the empire that Hefner eventually built. That kingdom shouldn't be known for its obsession with flesh but for the contradictions in the way it handled race, sex, and gender.

Hefner championed civil rights causes and published content from black authors and activists like James Baldwin, Martin Luther King Jr., and Malcolm X. Playboy featured black women as centerfolds in the '60s and '70s, and was one of the first magazines to put a black woman on its cover. It acknowledged black women as beautiful in ways that society refused to, and yet the enduring image of Hefner remains the shot of him, at various ages, surrounded by young, beautiful, mostly white women. That photo, and its symbolism, is seared into the minds of countless men as the pinnacle of manhood.

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Playboy and Hefner also mean different things to different women. For some, the Playboy life empowered women who wanted a seat at the king's table -- even if it sometimes meant first serving the meal while dressed in bunny ears and a fluffy tail. Kim Kardashian West, Jenny McCarthy, and Carmen Electra, all of whom posed for the cover of Playboy, shared fond memories of Hefner on social media after learning of his death. But for other women, the magazine and brand symbolized a new kind of repression: lust for the female body disguised as liberation.

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It's worth remembering that Hugh Hefner launched Playboy in 1953 by paying $500 for a nude photograph of Marilyn Monroe, which he used inside the magazine's inaugural issue.

The struggling actress posed for a photographer years before her movie career took off, according to the Washington Post. Hefner purchased the photo from a calendar company but reportedly never thanked Monroe, nor did he send her any proceeds from the issue's sales. Hefner did, however, buy a crypt next to hers in a Los Angeles cemetery and will spend eternity literally at her side. So Hefner's legacy might be best summed up as that of a man who seized financial and personal opportunities to glorify women in complicated, if not sometimes perverse, ways.

You could also consider Hefner a product of American culture and its marketplace demands, says Shelly Eversley, a feminist scholar and founder of the website Equality Archive. Hefner made a business opportunity out of both the male gaze and rebelling against prudish norms.

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"[D]id he really put this in men’s minds or did he just give them what he wanted?" asks Eversley.

Indeed, capitalizing on men's interest in women's bodies wasn't Hefner's invention. He just excelled at marketing a product that made some men feel worldly and virile and some women feel sophisticated and proudly sexual.

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Those ideas shouldn't necessarily inspire a knee-jerk reaction, but how they played out in the real world is something that definitely can. As Gloria Steinem famously wrote in her 1963 exposé about working undercover as a Playboy Bunny in Hefner's New York City club, being manhandled and groped was routine business. The staff, Steinem wrote, were also paid poorly and subjected to STD testing as well as invasive medical exams.

Hefner's legacy may be proof of how quickly sexual liberation can become a predatory pursuit when only men get to define the expectations and standards. His own personal life, and his habit of living with a gaggle of women who serviced his ego and sexual needs, would've looked more like the Handmaid's Tale had he not advertised it as glamorous for everyone involved. At least one account from Hefner's former girlfriend, Holly Madison, suggests he wasn't all that interested in whether or not those women had any real measure of freedom or independence.

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Still, Hefner considered himself a champion of gender equality, despite the fact that Playboy elevated sexist commentary from its inception and attacked "superfeminists" in the '70s. The magazine, however, also published articles arguing in favor of abortion rights, and Hefner's foundation supported the Equal Rights Amendment.

Contrasting examples like these demonstrate just how much of Hefner's legacy is a paradox. What you make of it depends on your values, beliefs, and experiences. In Hefner's case, the contradictions reveal the fault lines of American society -- sexuality, race, and gender -- and how easy it is to say you believe one thing but do another. In your efforts to dismantle one type of oppression, you might be successful for yourself but not others. You may also end up creating a new, sexier version of that oppression.

Whatever happens, it won't be simple or straightforward. Consider that the ultimate lesson of Hugh Hefner's legacy.