I have no doubt that there are many men, and not very many women, who were saddened by the news of Hugh Hefner's death. The men in question are, however, almost all adolescents either in age or spirit, unless they somehow shared in the financial wealth that Playboy magazine and its various cultural offshoots provided. I was, however, a bit more surprised by the tributes to him in mainstream media, praising him as an avatar of the sexual revolution and/or as a shrewd businessman who caught the waive of a changing set of American mores and rode it all the way to a business empire that many men would envy, whether or not they indulged in the fantasy life Hefner promoted.
Fantasy. In hindsight, that's probably the nicest thing that can be said about it. I am of the opinion that magazines like Playboy, and their smuttier counterparts, are far from being the gateway to a more fulfilling sex life. For far too many men, they are not a gateway at all. They are a dead end, a one-way ticket to a life of onanism that traps them physically and emotionally, and ends up being a barrier to meaningful sex--not only for the men in question, but for the women that could be their partners. The odds of paring off for women are statistically daunting as it is; rubbish like Playboy makes those odds worse, by training men Pavlov-style to only appreciate women who are airbushed (digitalized, later) into a "perfection" that doesn't exist.
And, in any event, Playboy was and is less of a celebration of sex than it was one of youth. Hefner claimed to be "liberating" women at the same time he was loosening up men's libidos. There was just one catch: the women in question had to be no older than their early 20's. After that, so far as Hefner was concerned, women shouldn't expect any sex in their lives at all, unless they somehow miraculously or surgically managed not to "age." Hefner, of course, didn't hold himself or other men to that standard; the more skeletal he became as he aged, the more grotesque he seemed by surrounding himself with women who were first young enough to be his sister, then young enough to be his daughter, and finally young enough to be his granddaughter and even great-granddaughter. Eventually, he needed phamacuetical help (both for him and his partners) to live up to the trap in which his "philosophy" had put him.
It is almost certainly not a coincidence that the peak of Hefner's cultural impact (and Playboy's sales) was in the 1960s, the peak period of boomer culture, the last decade in which Americans felt that they were always going to be young and rich forever. Hefner, perhaps, felt that way too. Had he really been the shrewdie he was supposed to have been, he would have seen the rising tide of even dirtier competition in his wake that would doom his position at the top of the skin heap, called it quits, and set up a foundation that would have truly pioneered free expression, without trying to commodify human beings for leering consumption.
In any event, given the exploration of sexaulity that was happening in other areas of the arts, Hefner gets far too much credit for liberating Americans from Puritanism, as worthy as that goal was. The revolution would have happened without him; all Hefner did was sell ammunition to its two greatest detractors: cultural conservatives and feminists.
That's way I'm inclined to think this is the fairest mainstream media assessment of the Playboy "legacy." And why I think Hugh Hefner, now gone, is best forgotten.
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