Hugh Hefner

Depending on who you ask, the life and legacy of Hugh Hefner is an interesting conversation. | Image: Luke Ford

If obituaries were simply a tally of the actions committed in a lifetime, it’d be easier to calculate the legacy of Hugh Hefner.  Though he can be credited with significant cultural change, it’s difficult to weigh the impact of a man who, to paraphrase a friend, “could have died in 1982 and ultimately accomplished the same amount of good.”

Hugh Hefner, the millionaire founder of the Playboy empire and father of four, died at home on Sept. 27at the age of 91. His widow, 31-year-old Crystal Harris (the briefest of his three marriages), was never added to his will. This quickly encapsulates the gender dynamics he espoused in his lifetime.

Hefner punched through puritanical ideas about sex, changed the landscape of publishing, and fully constructed a reality to fit his aspirations, but he did so by dangling poorly-paid, similarly-dimensioned women in front of men who aspired to replicate his sultan-like lifestyle.

For every celebrity friend (Little Kim! Rob Lowe! Gene Simmons! The Weeknd! Tomi Lahren?!) who eulogized the loss of an incredibly kind human, there’s a story from a former employee or girlfriend about living under the tyranny of a man who proudly claimed he had liberated women.

To tell the story of Hugh Hefner is to talk about women. Whether it’s a critique of his normalization of misogyny, a tribute to his iconic status, or an examination of his business acumen, women are integral to the story. Arguably it all started with one woman.

His first marriage was at the age of 22 to his college sweetheart, Mildred “Millie” Williams, with whom he had two children. It was this relationship that forever shaped Hefner’s approach to sexuality. The pair abstained from intercourse before marriage and she was his first lover. After the wedding, Hefner learned she had been unfaithful when they were engaged, while was away in the Army. Of the experience he said, “I had literally saved myself for my wife, but after we had sex she told me that she’d had an affair.

That was the most devastating moment in my life. My wife was more sexually experienced than I was. After that, I always felt in a sense that the other guy was in bed with us, too.”

This heartbreak inspired him to launch Playboy, a brand devoted to a bachelor lifestyle of faux-European sophistication and sexual liberation. Never again would “Hef” risk feeling betrayed by  women, as long as they were objects to be collected, rather than humans with whom he shared genuine intimacy. This narrative arc is equal parts American Dream incarnate, Red Pill forum commentator, and cartoon villain backstory.

The inaugural issue of Playboy in 1953 was wildly successful- in no small part to the cover model, Marilyn Monroe. It’s worth noting she had not consented to pose for the magazine and repeatedly begged Hefner not to use the images she had posed for in 1949, when she was an unknown, struggling actress. She had been paid $50 by the photographer who then sold the rights to Hefner for $500.

He claimed the publication was integral to her success, though Monroe says she only salvaged her career by publicly atoning for her participation in a series of groveling interviews.


What will be the legacy of this very human legend? For every young man inspired by the Playboy ethos and aided by the advice columns, there is undoubtedly a woman who stared dejectedly at her own body in a mirror, bemoaning her failure to fit the narrow beauty standards normalized by the magazine.


What of the women who made use of his platform to build their own? Pamela Anderson, Jenny McCarthy, Jayne Mansfield, Carmen Electra, Anna Nicole Smith and other notable beauties can thank Playboy for helping to launch their careers. Ironically, perhaps so can feminist Gloria Steinem whose groundbreaking article A Bunny’s Tale, an expose of her time employed as a Bunny at a Playboy club, remains a standard for undercover journalism. In the piece, Steinem detailed the problematic working conditions that included: requiring a gynecological exam for employment, rules against weight gain, emotionally abusive management practices that pitted women against each other, and never making the amount of income the job had advertised.


Then there are women like Holly Madison and Kendra Wilkinson, who are famous mostly for having dated Hefner. Through his marketing power, it was possible to make millionaires of people lacking any demonstrable talents. For this they have expressed gratitude, albeit mixed with stories of dehumanizing treatment. Several former girlfriends have written about obligatory passion-less, mechanized orgies, strict 9pm curfews, orchestrated strife between women, and financial domination.


Former girlfriend Izabella St James wrote in her memoir Bunny Tales: Behind Closed Doors at the Playboy Mansion, about the weekly ritual of waiting in line for their $1000 allowance. “We all hated this process. Hef would always use the occasion to bring up anything he wasn't happy about in the relationship,” and “He used it as a weapon." Kendra Wilkinson told US Weekly, “I hate putting my hand out, but we couldn't have jobs other than getting appearance fees.”


What of Hefner, the civil rights activist, who pushed the sexual boundaries of mainstream culture? In a 2016 issue of Playboy (during the brief era in which the magazine decided to no longer publish nudes), Hefner wrote an article in which he declared victory for freedom over conservatism, citing the failure of Ted Cruz’s campaign for Presidency and the legalization of same-sex marriage.


“We have already won those battles, and we will win them again,” he said, “These are the final skirmishes of a retreating army of self-appointed moral authorities who have been defeated again and again for the past five decades. Americans have rejected these religious fanatics and fought to protect women’s rights, reproductive rights and our right to privacy rather than submit to their Christian view that sex exists for the sole purpose of procreation.”

Upon the execution of his will, charities will benefit from his amassed fortune, as he gave generously in life. An early champion of racial integration, reasonable drug policies, first amendment and LGBT rights, libertarian Hefner always seemed to align with social justice movements that had direct benefits to his sybarite lifestyle. It only makes sense he would campaign for contraceptive and abortion access, since, as several former girlfriends have stated, he refused to wear condoms.

What will be the legacy of this very human legend? For every young man inspired by the Playboy ethos and aided by the advice columns, there is undoubtedly a woman who stared dejectedly at her own body in a mirror, bemoaning her failure to fit the narrow beauty standards normalized by the magazine. For each sexual taboo that was shattered, some rigid sexist or capitalist totem was reinforced. Hefner’s is a legacy that will continue to be crafted, as our ideas about sex and gender evolve.

One thing that is sure: thanks to a $75,000 plot purchase he made in the 90s, Hefner’s body will be interred next to that of Marilyn Monroe, a woman he never met. It’s the perfect summation of the man forever motivated by a desire to be in proximity to (but not genuinely connected with) iconic women.



(1) comment


Excellent summary! I agree he hadn’t contributed anything since the 80’s. I think he also skewed the whole country toward his breast fetish, which certainly isn’t universal.

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