Hugh Hefner was a millionaire extraordinaire that built his empire on sexuality and free speech. The ultimate embodiment of the playboy lifestyle that every adolescent boy dreamt of at one point of their childhood, Hefner led the (very controversial) way as a media pioneer and advocate for sexual liberation with a single magazine – Playboy. While he passed on just two days ago at the age of 91, Hefner left behind a legacy as the creator of the most successful men’s magazine ever.
Hefner was miles ahead of his time, debuting a magazine that was making waves with interviews as revealing as the centrefolds. In other words, the Playboy was considered adult entertainment for men. However, if you take a look at the articles without the pictorials, they were controversial, cutting-edge stuff that was at the heart of journalism.
Hugh Hefner and the very first issue of Playboy
Not only did Hefner allow girls to tell the stories that they were afraid to reveal to the public, he also used Playboy as a platform to support the LGBT community. In 1955, Playboy published ‘The Crooked Man’ by Charles Beaumont, which was a story set in a future where the majority of the population was gay and heterosexual men were the ones getting persecuted. Playboy wasn’t just entertainment for men; it was also all about encouraging individuals to live the life they want to live. The magazine covers and editorial shoots from the first few decades bordered on the artistic and experimental, unlike the racier covers that we see today.
Ironically, Hefner’s reputation as a hip, liberal activist was attacked by feminists in the 1970s, who accused Playboy for sexualising women as sex objects. But no matter what you thought of Hugh Hefner, you couldn’t deny that Playboy was a cultural force that redefined sexual freedom for men and women alike.
Here are 8 of Playboy’s most iconic covers and the stories behind them.
Dec 1953: Marilyn Monroe
It all started with a nude photo, and one of Marilyn Monroe at that. Hefner bought a black and white shot off a Chicago calendar company and placed it on the cover of the very first issue of Playboy that wasn’t even numbered, together with some nude shots of Monroe inside. No one knew how big Playboy and Marilyn Monroe would eventually become, leaving behind a legacy that will be remembered for eons. Hefner will now be buried in the crypt next to Marilyn Monroe’s plot in Westwood Village Memorial Park, which he bought for $75,000 in 1992.
Every cover has two core artistic elements: the model and rabbit head logo. The May 1964 cover saw Donna Michelle becoming the brand herself, easily twisting into the shape of the Playboy rabbit and still looking seductive on one of the magazine’s most ambitious and creative covers ever.
Nov 1975: Patricia Margot McClain
This was the cover that ultimately made Hefner realise that he nearly crossed the line amidst The Pubic War with Penthouse, whose emergence on the print scene in 1969 threatened to dethrone Playboy by featuring racier and explicit content in a bid to win readers. Playboy was a classier gentleman, and Hefner vowed never to stoop to Penthouse’s aesthetics ever again after this cover. This cover was chalked up to the benefit of the doubt, where publications such as Newsweek describing McClain who “seems to be plumbing the depths of her bikini panties for a stray kernel of popcorn.”
Oct 1977: Barbra Streisand
Nothing like a Jewish actress and singer to really get the rumour mill going. Barbra Streisand also granted Playboy a super in-depth interview in which she clarifies stories and rumours about her, revealing a much more complex side to her. And yes, Streisand also posed in the iconic bunny outfit, which she refused to let go to print. 10 years later, Streisand revealed that it was one of her biggest regrets because she was afraid of being attacked by feminists.
Sep 1985: Madonna
Being famous was never easy, and most celebrities have pasts that they aren’t proud of. Madonna is no different. When Playboy dropped black and white nudes that she shot as a nude model in her 20s to pay the bills, Madonna wasn’t happy about it but couldn’t stop publication.
Mar 1990: Brandi Brandt and … Donald Trump
We can’t say we were too surprised when we discovered this one, but it is definitely an iconic one. Meet circa 1990 Trump, one of the very few men to take the cover of Playboy. While Trump is very proud of the cover, having been spotted autographing copies of the magazine during his presidential election, Hefner and his son, Cooper, can only describe this cover in one word – embarrassment. In a series of tweets, Cooper said that had the editorial team then known about Trump’s values now, the President would never have found his way onto the cover because what he stands for today is totally against the philosophy of Playboy.
Fun fact: 1990 Trump told Playboy that he was “one hundred percent sure” he does not want to be president unless he saw “this country continue to go down the tubes.” You can go dig up Trump’s interview, where he answered a variety of questions regarding what he would do as president and how he, at the time, perceived other countries and leaders, and bask in the irony of America today.
As for Brandi Brandt, the quintessential California rock goddess of the 1980s and early ’90s, she is currently in jail for smuggling drugs. One’s in jail, and the other is president – we could never have predicted this when the cover was first shot.
Aug 1994: Carol Shaya
Here’s another one for the controversial collection. Playboy actually got a NYPD officer, Carol Shaya, to appear on the cover, along with an accompanying nude pictorial (women in uniform are definitely sexy) inside. Not surprisingly, Shaya was promptly fired when this issue hit the stand for unauthorised off-duty employment and improper use of her uniform and the NYPD logo.
Nov 2009: Marge Simpson
Everyone’s favourite animated mom reveals her frisky side in one of Playboy’s most interesting and satirical covers ever. If you ever get your hands on this issue, you’ll also see some nudes of Marge Simpson, ensuring that you’ll never view the Simpson family the same way again. Surprisingly, the Simpsons seem to have very human-like anatomy, just in case you were wondering.
Header images from Playboy archives
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