Hugh Hefner, perhaps the most famous—and infamous—magazine mogul in history has died at the age of 91. Some readers will no doubt remember him as the swingin’ uncle who helped you discover earthly delights during puberty, while others will say good-riddance to a man who, to them, largely personified a decades-old war on family values.

And he may well have been both. A man with more contradictions than a kaleidoscope, for better and for worse, Hef was the man who helped light the match that exploded into the sexual revolution the Boomers and Xers and Millennials all take for granted today.

When we think of the 1950s and early 60s, we tend to think of it as a world seen in black & white (in more ways than one)—as either a golden age of suburban patriotism and family values, or a dark age of repression, open sexism, gray-flanneled conformity and thinly-disguised racism. But there was another 1950s that existed beneath the placid, pot-roast-and-mashed-potatoes surface: an era of beatniks, joke books, great film noir, the Hungry I, Mort Sahl, Sid Caesar, and progressive jazz.         

And nothing better epitomized this era than when Playboy first hit the stands (or was delivered in plain brown wrapper) in late 1953, with the ultimate sex goddess of all time, Marilyn Monroe, as its cover girl. Before Mad Men monsignor Matthew Weiner was even born, Hugh Hefner (along with Frankie, Deano, Sammy, and JFK) was a living, breathing invisible bridge between the postwar 50s and the Summer of Love 60s—and everything that came since.

At the time, pornographic material, and the use of the U.S. Postal Service to disseminate porn, was illegal. That of course brought up the question of what, exactly constituted porn in black-letter law? Certainly anything involving children or animals, but what about consenting adults? Even Supreme Court Justice Potter Stewart couldn’t do any better than “I know it when I see it.”  

No one, of course, would bother to defend pure smut with “no redeeming social value.” And here was Hef’s masterstroke: What if someone published a high-gloss magazine with articles by up-and-coming, even respected writers, on politics, pop culture, and psychology, around the sizzling-hot centerfolds? While it became something of a joke for people to say that they read Playboy “for the articles,” there was actually a reason for doing just that. The magazine would feature articles by writers like Norman Mailer, Saul Bellow, Alex Haley, John Irving, Woodward & Bernstein, Siskel & Ebert, and Joyce Carol Oates to name but a few.    

From both the conservative and liberal perspective, Hefner’s political legacy was to illustrate myriad double standards and inconvenient truths. As no less a lefty than Freddie deBoer noted, while social conservatives may have been wrong (in his opinion) on the issues, they were actually right more often than not when they predicted that if you gave people an inch, they would take a mile. When the Civil Rights Act was up for debate in the 1960s, it is said that Hubert Humphrey promised on the Senate floor to “eat this bill” if it EVER led to things like quotas or forced busing (one hopes Mr. Humphrey had fries and a glass of Coke to help wash it down.) When Phyllis Schlafly and Anita Bryant said that “equal rights” for women would lead to women in front-line combat, gay marriage, abortion on demand, and transgender bathrooms, 1970s liberals said they were nothing but fear-mongering fundamentalists. You can debate the results, but the progression began with that one little spark.

And so it went with Playboy. The plush, burgundy red door to normalizing and mainstreaming porn that Hefner tantalizingly cracked open in the ‘50s and ‘60s was well and truly obliterated— first by the hard core “dirty mags” of Hustler and Screw and the 1970’s porn film industry, and then by the really “anything goes” era of today’s Internet pornography.

Hef’s impact was no less divisive for liberals. On one hand they had to see Hefner (and later, the far less defensible self-proclaimed “smut peddler” Larry Flynt) as champions of First Amendment-protected free expression, who helped to throw off the Victorian-era shackles on sexuality. On the other, Hefner made his fortune off objectifying young women. In an obituary for the short-lived but notorious 1979 Chuck Barris game show, Three’s a Crowd (which pitted a man’s wife or girlfriend against his secretary or lady associates from the office, to see which one… umm…  knew the man better…), I remember reading a line that said something to the effect that loathing the program “was one of the few things that both feminist groups and the Religious Right—two groups that were otherwise completely inimical to each other—could agree on.”  

But nothing brought feminists and fundamentalists together like Playboy and Penthouse, and the “porno chic” that followed it during the Deep Throat/Boogie Nights era. A young and sexy Gloria Steinem got her start when she went “undercover” as a Playboy bunny in the ‘60s, and then wrote a seminal essay about it.

There was just one little snag—Hugh Hefner himself would be the first to insist that his women weren’t just sex objects. One of the things that even non-connoisseurs of Playboy know is that Hefner’s angels were never just nameless, faceless dolls, like so much of porn that came up afterward. Barbi Benton was a trained pianist and comedienne. Classic-era Price is Right queen Janice Pennington was a ‘60s supermodel and dancer who later went on to co-found the Hollywood Film Festival. And of course Jayne Mansfield was a legitimate movie star and a pro-level violinist to boot. Future Falcon Crest, Dharma & Greg, and Castle queen Susan Sullivan got her start as a Shakespeare-spouting Playboy Bunny while looking for work as a stage ingénue in the ‘60s. And do we even need to discuss Marilyn Monroe? Playmates were encouraged to open up about their interests, their sense of humor, their individual tastes and personalities, in the sidebars and interviews that accompanied their centerfolds, full-frontals and skin shots.

And while Hefner embodied the liberated 1970s of Charlie’s Angels, Three’s Company, Dallas, The Gong Show, just as much as he did the Eisenhower-era cocktail lounges, he also demonstrated in no uncertain terms the high price that kind of lifestyle sometimes came with. In January of 1975, his longtime live-in personal assistant, Bobbie Arnstein, committed suicide after being arrested and sentenced on trumped-up drug charges, which Hef believed were the J. Edgar/Mark Felt FBI’s way of getting back at him for his libertine ways and staunch campaign against the “war on drugs.” Two of his most unforgettable—and also most legitimately talented and intelligent—Playmates of that time also died tragically: Claudia Jennings, in an October 1979 car accident; and most notoriously of all, Dorothy Stratten, in an August 1980 rape-murder and suicide at the hands of her former manager and ex-husband.                                                                       

Hef was truly shaken by these losses, and with the dual rise of AIDS on one hand, and the Moral Majority on the other, Hefner’s true heyday was itself coming to an end. But Hef never really went away. His pleasure-palace Playboy mansion, with its famous grotto swimming pool and panoramic views, will forever remain a pop-culture icon, synonymous with the absolute A-list in Hollywood (and political fundraising). His Playboy Jazz Festival was an artistic endowment for countless young up-and-coming spit-valvers and song stylists (and many not-so-young greats). And his Playboy Clubs were ground-zero for top comedy and music talent of their day, from edgy greats like George Carlin and Redd Foxx, to pie-in-the-face family men like Soupy Sales.

[youtube https://www.youtube.com/watch?v=f7kjOPCxLC0&w=560&h=315]
And as he recedes now into the twilight of Tinseltown’s spotlight, it’s perhaps best to remember Hef in his swing-a-ding-ding heyday, capped by his Playboy After Dark variety show in 1969. He was the icon of cool-cat, three-martini Greatest Generation hipsterdom, of Rat Pack-era Hollywood and Vegas, the Don Draper of porn.

And even if you thought he was nothing but a hedonist who mainstreamed misogyny and porn, it must be noted that Hef was much classier than anyone in his “industry” who came up after him. In any case, let’s charge the wailing and geschrei and gnashing of teeth that usually accompanies death to someone else’s account. Love him or hate him, Hugh Hefner was the kind of guy who would’ve wanted you to disco-dance on his grave.  

Telly Davidson is the author of a new book on the politics and pop culture of the ’90s, Culture War. He has written on culture for ATTN, FrumForum, All About Jazz, FilmStew, and Guitar Player, and worked on the Emmy-nominated PBS series Pioneers of Television – and he also wrote a swingin ‘60s and ‘70s book about TV’s Grooviest Variety Shows.