Hugh Hefner with a group of Bunnies at the flagship Playboy Club, in Chicago, circa 1960. (Associated Press)

The death of a 91-year-old horndog (Oh, come now — Hugh Hefner’s existence was dedicated, if nothing else, to words like “horndog” being allowed in a family newspaper) feels like the end of an era that we’ll never be allowed to stop debating. He liberated women by putting them in rabbit costumes. He rode the wave of the sexual revolution, and then spent the next half-century dressing like a theater nerd whose headwear was furnished by an “Anchors Aweigh” postproduction tag sale.

He represented sex but hadn’t been sexy in a long time. This was due far less to age than to paisley pajamas and that captain’s cap.

And through it all, there was the perpetual question of the F-word, which his empire was built on and played off of. Not the one that rhymes with “duck,” but “Feminism” — which is infinitely more complicated, and always a buzzkill to bring up one day after an icon’s death. But was Hugh Hefner, in the end — was Hugh Hefner good for the ladies?

He thought so, it seemed. He saw sexual liberation as hand in hand with the civil rights movement. He frequently talked about how the sweeping away of prudish attitudes benefited nobody more than it benefited women, which was probably true. He launched the careers of scores of now-powerful women, and sometimes — Joan Collins on the cover of Playboy at the age of 50 — his choices were innovative and progressive.

But his choices were more often than not blond, thin, bulging, game. They were always up for a good time or down for a good time, and always liking whatever it was that you liked. Always sweet, never too independent. Long before the writer Gillian Flynn popularized the concept of the insufferable “Cool Girl,” who doesn’t exist except in men’s fervent fantasies, Hugh Hefner dreamed her, undressed her, and put her in his magazine.

The result might have been to give women more options, but the reverse was that it gave men more expectations. It was still ideal womanhood as men perceived it and not as a woman perceived herself: naked, but devoted and dependent, with lots of walks on the beach.

Hefner poses with a Chicago hostess, Bonnie J. Halpin. (Ed Kitch/AP)

Or, as one man did. (Not all men, Playboy readers! Not all men!). Hef’s personal ideal was the one channeled onto Playboy’s pages.

And if his personal version of womanhood was parked permanently in the ’50s, his version of manhood was parked permanently in his own teens. “Much of my life has been like an adolescent dream of an adult life,” he once told the Los Angeles Times. “If you were still a boy, in almost a Peter Pan kind of way, and could have just the perfect life you wanted to have, that’s the life I invented for myself.”

What kind of person would choose to live in a child's fantasy rather than a grown-up one? Or, don't answer that, since the answer might be, "All of us, if we only had the money." A better question might be, What kind of cohort allows itself to be defined by the sexual expectations of an inexperienced 13-year-old?

Because that’s essentially what happened, for thousands of Hef’s admirers. His origin story — that he was irrevocably damaged in 1949 by learning that his first wife had cheated on him — has a whiff of prototypical Reddit red-pill whininess to it. “I was absolutely devastated,” he said in a 1994 interview. “I’m sure in some way, that experience set me up for the life that followed.”

The devastation would be normal. Less normal is the response of creating a whole empire around the idea that women can’t be trusted and so they should instead be imprisoned in the purgatory between raunch and domesticity.

When Holly Madison, Hef’s former chief girlfriend, came out with a tell-all book about life in the Mansion, the most bizarre revelation was that, prior to the man’s infamous orgies, all of the live-in girlfriends were required to put on matching pink flannel pajamas.

Hefner in 1977. (George Brich/AP)

But that was Hugh Hefner for you. Nostalgic for some time that never existed, wherein women dutifully obeyed a 9 p.m. curfew (a requirement for live-in girlfriends) and cuddled up for family movie night, but they also couldn't wait to jump into a pair of three-inch heels and into a night of harem duties. In 2013, an Esquire writer did a deep dive into the mansion itself, with its threadbare sofas and nightly desserts of apple pie and ice cream sundaes, and Esquire concluded that the place had the vibe of less a sex palace than a grandmother's living room.

Think of those threadbare sofas and it’s almost impossible to dislike Hugh Hefner. For all of his pageantry, as he got older he got quainter. He certainly didn’t seem to belong in this current grab-’em-by-the-kitty era. By the end of his life, one has a far easier time picturing Hugh Hefner buying his girlfriend a comfy pair of slippers than one of the satin corsets the Bunnies used to wear.

“We will never recapture the importance of Playboy in the ’60s and ’70s,” he told The Washington Post in 2003, “because we changed the world. We live in a Playboy world now, for good or ill.”

He helped create a world that we then all lived up to, aspiring to a pubescent worldview. He did help forward the sexual revolution, but his view of it was narrow: the sex part of it. The part where women he found specifically attractive were free to have sex. Was that enough? Was that enough for him to be a hero for women, or just to be a god among men? Maybe, for feminists, he can be a Playmate of the Month for a shorter month. February not on a leap year. That’s all.

He’ll be laid to rest permanently in the cemetery slot next to Marilyn Monroe. Incidentally Hefner, the man given credit for launching Monroe’s career as a sexbomb, never asked her permission to do so. The nude photos that appeared in Playboy’s first issue weren’t intended for the magazine — they’d been shot years before when Monroe was penniless and desperate. She didn’t think they’d become so public, but Hefner found and bought and published them, and Monroe grew into that persona and later embraced it and became world famous.

It’s a parable, in some ways, for Hef’s relationship with womankind. Give them power, but on his terms. Make them famous, keep them nude. Change the course of their history, for good or ill, and then stick next to them for all of eternity.