Hugh Hefner's Crumbling Empire of Ickiness

He’s such a cool guy!

It’s hard to overstate the role Playboy played in the minds and sexual development of multiple generations of horny young straight men. 

Playboy was masturbatory fodder first and foremost. Before the internet, Playboy was where you went to see the naked breasts of impossibly beautiful young women. 

To the fourteen year old me at least, Playboy wasn’t just a spank mag or something to look at while pleasuring myself: it was classy. It was prestigious. It was smart. It was politically engaged. It was iconic. It was Americana. It was on the right side of history. 

Playboy was upscale, aspirational. It wasn’t just a magazine, it was a way of life, a philosophy, a way of looking at the world. At the center of it all was the glamorous, enviable figure of Hugh Hefner, a wealthy gentleman habitually clad in pajamas and puffing paternalistically on a pipe while presiding benevolently over his empire of lust, sex and money. 

If someone criticized Hefner as a pornographer or predator,  I felt duty bound to remind them that the magazine magnate was so much more than a guy who got rich and famous from selling pictures of naked ladies to horny dudes. 

I would point out that Hefner provided opportunities for black entertainers to perform at his clubs at a time when segregation still reigned, helped fund the cases that led to the landmark Roe Vs. Wade hearing and published the work of great writers and wits. 

Besides, if Hefner was such a creep would he really hang out with brilliant comedians like his best friend Bill Cosby or Woody Allen? Would he personally fun his good friend Roman Polanski’s MacBeth?

The older I got, the less enamored I became of the Playboy mystique. It became less an ideal than a toxic fantasy that was impossible to sustain. 

I respected and admired Hugh Hefner as a young man but over time I have lost all respect for Hefner and Playboy. 

In 2016 I wrote up Holly Madison’s scathing tell-all Down the Rabbit Hole for my Silly Little Show-Biz Book Club column over at The A.V Club and while the former Playmate and Girls Next Door star comes off terribly in her memoir Hefner comes off even worse. 

A man I once foolishly saw as the very epitome of class and sophistication is convincingly depicted as a pathetic codger desperately trying to hold onto an image as a debonair lady’s man deep into old age. 

Hefner almost could not come off worse. There are a lot of horrifying moments in Madion’s expose but the most horrifying involves the reality show star stumbling upon her ostensible boyfriend’s bestiality porn. 

The Playboy founder’s penchant for bestiality apparently figures in a new docu-series called Secrets of Playboy that depicts Hefner as a monster as well.

I don’t care how many pieces of incisive short fiction someone publishes: if they’re into bestiality and snuff films they should be cancelled as aggressively as humanly possible, even if that cancellation is posthumous in nature. 

My perception of Hefner and Playboy was also affected by a story the loathsome Bob Zmuda tells in his most recent book about tricking inveterate star-fucker Hugh Hefner and a Playmate into thinking that Jim Carrey was inhabiting the role of abrasive lounge lizard Tony Clifton during a trip to the Playboy Mansion when it was actually Zmuda. 

Zmuda brags about having sex with a Playmate who thought she was having sex with the star of The Mask and Eternal Sunshine of the Spotless Mind. Zmuda comes off terribly in the anecdote but so does Hefner. 

Reading what’s supposed to be an outrageous prank at the expense of an arrogant buffoon but actually feels more like an opportunistic sexual assault made me wonder just how many other vulnerable young women were violated by the rich and famous at the Playboy Mansion through the decades. 

Playboy’s storied history and legendary founder used to be its greatest asset. Now they’re its greatest weakness. Playboy, a magazine famous for running pictures of naked ladies, no longer runs pictures of naked ladies and now seems understandably eager to distance itself from its founder and the many sex crimes he is accused of.

Playboy may or may not survive in the years and decades ahead but the infinitely flattering self-mythology that Hefner spent decades cultivating is dead and gone, a poisonous lie that could not, and should not, survive the moral and spiritual reckonings of the #MeToo era. 

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