By Kai-Lin Wei

Hugh Hefner was 27 when he published the first edition of Playboy, a 42-page paperback featuring a nude Marilyn Monroe on both the cover and centerfold. All 50,000 first-run copies sold out in one day. Playboy would go on to launch this young, charismatic editor-publisher into cultural stardom: Depending on who you asked, Hefner was either a revolutionary sexual liberator or — perhaps more realistically — just another mogul with too much power. Only five years after the release of Playboy #1, Hefner purchased the “original” Playboy Mansion in 1959, a 70-room brick and limestone residence in Chicago's Gold Coast, and then the more notorious Playboy Mansion West in 1971, a sprawling 2,000-square-foot house in west LA, complete with a zoo, aviary, grotto, game house, and basketball and tennis courts.

Simultaneously his place of residence and a private clubhouse known for its lavish sex parties attended by the upper echelons of society, Hefner — visionary, boyish, chock-full of Old American mystique — took a sexually repressed post-WWII America by storm when he brought into the Playboy Mansion a brave new world of sexual liberalism, decorated with the undeniable Jazz Age Gatsby-esque influences of his childhood. In the 2022 docuseries The Secrets of Playboy, shots of skinny, technicolor-clad bunny girls (“Playmates”) sprawled along loveseats are intercut with Hefner’s voice, admitting to the audience privately, coyly, “Much of what Playboy’s all about, really, is a Disneyland for adults, a projection of those adolescent dreams and fantasies that I had growing up, that I’ve never really lost.”

Dreaming is affixed to the center of the sexual landscape, perhaps because the cognitive distortion that occurs when we enter the dreaming world and the sexual world elicits the same feelings of elusiveness, secrecy, and ecstatic disorientation. In the sensate ether of the Playboy Mansion where Hefner’s twice-weekly parties thrummed with electricity and extravagance, some approximation of heaven was always being chased after: boys looking for trouble, girls looking for fame, old men looking for scraps of beauty in their cold, empty worlds, and women who knew just where to find it for them, because they had once been beautiful themselves. There in the crowd writhed one thousand broken hearts begging to be healed, one thousand broken bodies begging to be touched.





A laissez-faire attitude guided much of Hefner’s life and work with Playboy. Rules were boring, propriety was stifling, it should be OK to say whatever (and sleep with whomever) you wanted “as long as you weren’t hurting anyone,” and the emergent generation of young American men ought to be intellectual, progressivist, and liberated — just like the gentlemen who subscribed to the Playboy lifestyle. Unlike the cheap stashes of “porno mags” lining the lower shelves of gas station stores, Playboy was sexy, classy, and sophisticated. Right alongside spreads of nude women were incisive op-eds and interviews with the likes of Malcolm X, Stephen King, and Al Pacino. Hefner himself spoke out against segregation often — Black and white Playmates lived together, worked together, were paid the same — and advocated for freedom of speech.

“It was such a lifestyle,” Pamela Anderson once said in an interview with the Los Angeles Times. “Playboy Mansion was like my university. It was full of intellectuals, sex, rock ’n roll, art, all the important stuff.” It was this interweaving of sex rituals — something perceived by Hefner’s preceding generation as shameful, dirty, and forbidden — into a cultural ethos that held its head high in the light of day that ultimately earned Hefner his cultural preeminence as a “sexual liberator” in the ’50s and ’60s. Sex was now something clever people had, enjoyed, and owned up to; and at least as it related to Hefner’s double-sided legacy, the pushing of this needle certainly paints Hefner in his most flattering light.

Unfortunately, all that makes sex desirable, from its midnight phantasmagorias to its uncontrollable ecstasies and agonies, also makes it dangerous. Hefner did perhaps set out to challenge sex culture in the early days of Playboy — an argument can even be made that he succeeded. But he also invited something more monstrous than he knew into his house, and by extension, the new psychosexual culture which he had embedded into the American conscience. The surrealness of sex makes tangible accountability difficult, something Hefner in his later years liberally exploited. Running like a scar along the underbelly of Playboy Mansion’s celebration of sexual freedom was the cycle of abuse that kept the party going: repeated allegations of the sexual assault and even suicides of Playmates first emerged in the ’70s, then were successively disappeared by Hefner’s “cleanup crew.”

Much of the abuse happened in a psychological twilight zone: in the disorienting, drug-addled moments leading up to sex, during the unwilling act of it, and afterwards, when it was all over — when, waking to the cheerful morning light shining upon the lush acres of Hefner’s estate, it felt like you must have only woken up from a bad, bad dream. Somewhere along the way, Hefner must have realized this truth, too: that you could buy and sell sex at your leisure, or use it to invoke in somebody any primal human emotion you’d like, whether it was love, shame, guilt, or terror, and it would all go more or less unpunished. It was astonishing what could be forgiven and forgotten in the light of day, what little effort was required to keep these sorts of unsightly narratives from rearing their heads in public.

Even today, in a world that is becoming increasingly unrecognizable to our evolutionary faculties, sex has retained a core position in our collective human culture. It proliferates in an otherwise austere cyberspace and enmeshes itself within our sophisticated economies. We need it, we crave it, we would do unspeakable things to get it. There is, after all, a reason why men in power almost always use that power to realize their sexual desires. Sex is the one part of our original humanity we can’t seem to originate from. The need to feel good is simply too strong, too permanent. What ensures our survival, it seems, also ensures our cruelty.





Following Hefner’s death in 2017, more accounts of sexual assault, drug abuse, and underage prostitution within the mansion have come to light. We, of course, condemned the deadman, sold his estate, and quietly seized his assets to split amongst ourselves. Now both the Playboy Mansion and its landlord’s legacy sit shoulder-to-shoulder in our cultural graveyard: emptied out, decaying, another plain-faced relic of the deceitfully fabulous past, cautioning us against a worser nature we all deny we possess. No wonder why we despise sex so much: it runs countercurrent to what makes us different from animals, undermining our seat of power as self-possessed creatures. It shows us the truth about ourselves. And when we say, “Maybe we can learn from this,” it is the little voice that quips, “Or maybe not!”

Make no mistake: Hefner’s refusal to separate reality from the sensual fantasy which his franchise popularized and profited millions off of was only an early omen of our continued participation in the intimacy economy today. We stake everything — morality, connection, control — on only a few brief moments of ecstasy. How, we ask ourselves with disgust, could we have let this happen?

The answer remains the same each time. How could you have not? ■