The passing of Playboy creator Hugh Hefner at the impressive age of 91 marks the end of a life that had an enormous impact on media, culture, and sex. Hefner will be for the most part hailed this week as having a legacy of progressive advancement of sexual mores, with nostalgic references to the culture of free love and plaudits as a champion in the libertine battle against prudish Bible thumpers. But in fact, Hefner’s legacy is much more complicated than that, and much of Playboy’s struggles in recent years have more to do with the persistence of an underlying conservatism and traditionalism in view of sex roles and the nature of manhood. The inheritors of his magazine have attempted in awkward fashion to shove the now-problematic aspectsof Hefner’s worldview out of view – including, in a most obvious fashion, the very thing he was known for in the first place. But it turned out that yes, the magazine still needed pictures of naked ladies to sell.

Hefner’s bet in 1953 was an salacious one at the time, but now it seems practically quaint. Hefner saw art in the naked female form. He saw the value in a purposeful life, but preferred it be more hedonistic. He liked fine tobacco and strong cocktails and stylish dress and fast cars, all while permanently surrounded by a habitat of gorgeous and willing women. Hefner was creating a brand out of thin air, and his publication was a presentation. It was a thumb in the eye of contemporary mores.