But for all the assumptions that Hef’s life was every man’s fantasy, he also shortchanged men. He told them the best way to be a man was to implicitly treat women as the enemy, as products to consume. It is a grim, banal, consumerist way of life that, in practice, would deny men the pleasures of being partners to women, sexually or otherwise.

Hefner launched Playboy magazine in 1954 amid a flurry of articles worrying that masculinity was in “crisis,” under threat from overbearing women. Playboy, with its celebration of leisure, played into some of those critics’ fears of weak postwar men, but everyone could agree women were to blame. “Take a good look at the sorry, regimented husbands trudging down every woman-dominated street in this woman-dominated land,” Playboy columnist Burt Zollo wrote in an early issue in one of several stories the magazine would run bemoaning the “womanization” of men. A half-century later, in an interview with Carrie Pitzulo for her book, “Bachelors and Bunnies: The Sexual Politics of Playboy,” Hefner explained that “the womanization of America” was related to “prohibition, anti-sexuality, censorship.” He mentioned to her how prudish his mother had been.

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Throughout his life, Hefner seemed to vacillate between terror of women and a desire to control them. In 1970, Steinem described his magazine’s worldview as “boyish, undeveloped, anti-sensual, vicarious and sad.” (When the two met to accept an award almost 30 years later, the New York Times described Hefner as shaken by Steinem’s cold fury, and “crumpled, almost deflated.”)

As he aged, still clutching his pipe and forever in his pajamas, Hefner became a real-life version of the overage character in “Dazed and Confused” who exults about high school girls: “I keep getting older, they stay the same age.” In an account from one of his partners, Holly Madison, Hefner was controlling and manipulative, but also held in utter contempt by the women of the mansion, who apparently drew no pleasure from spending time with him. It’s hard to call a very rich man who supposedly won what every man wanted sad, but from where I sit, this inability to connect with women as humans was depressing.

When feminism grew more fashionable in the 1970s, Hefner draped himself in civil liberties and funded organizations like the ACLU, including, early on, its Women’s Rights Project, while still taking care to distinguish the “good” feminists (who favored access to abortion and contraception) from the “bad” (who would make Hugh Hefner feel bad about his erection). He even took credit for teaching the women how to free themselves: “Playboy was there from the beginning, before feminists even had their voice, fighting for birth control and abortion rights.” But Hefner and the men who wanted to be like him could have learned a lot from the critiques of the feminists he dismissed, if they had cared to listen.

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For many feminists, the problem with the midcentury sexual revolution wasn’t the no-strings-attached sex; it was that they were “free” to have sex on men’s terms — and, in the absence of social, economic and political power, this wasn’t exactly liberation. Another problem was that men, and not just women, have feelings, too, including when it comes to sex, something that Hefner’s world never broached. “Was the rejection of any link between sexual desire and emotional involvement really an expression of freedom — or merely another form of repression?” wrote feminist critic Ellen Willis in 1982. The “predatory disregard of women as people,” she added, was “an attitude that could only reinforce the conventionally feminine sexual reluctance, passivity and unresponsiveness that men found so frustrating.” If Hefner and Playboy had bothered portraying women as human — with desires and complications and messiness and weirdness — could their male readers have had better sex lives?