60 Years of Playboy

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In honor of Hugh Hefner's birthday, we take a look back at some of the most iconic Playboy covers.


Everyone’s favorite octogenarian is celebrating his 87th birthday tomorrow. No, not Rupert Murdoch—no one likes that guy! I’m talking about the Double-H, Dirty Mag Dan, the Entrepreneur Extraordinaire, Hugh Hefner. It’s been almost 60 years since the first issue of Playboy was released, and in that time, the media empire has influenced the aesthetics of print pornography and laid the groundwork for movies starring Anna Faris (The House Bunny, circa 2008 ). And let’s not forget the words: Playboy has published work by the likes of Vladimir Nabokov, Chuck Palahniuk, P.G. Wodehouse, and Hunter S. Thompson. We have it on good authority Hugh doesn’t like cakes or surprise parties, so to celebrate the day of his earthly awakening, we scoured the web (and our brains) for some of the most memorable Playboy covers, and put them all in one place for your browsing pleasure. 


The first issue of Playboy ran in December 1953. Hefner produced the zine in his Hyde Park, Illinois kitchen, and didn’t date the issue because he wasn’t sure there was going to be a second one. Hefner purchased the photos from a local printer, but still named Marilyn the "Sweetheart" (soon to be "Playmate) of the Month. 


This issue forgoes the standard woman-smiling-coyly approach and opts instead for the more mysterious dog’s-eye-view. Apparently (at least in the beginning) it was Hefner’s goal to feature the bunny logo somewhere on each cover, sometimes hidden in the background. This time? Not so hard to spot. 


Darine Stern was the first black model to have a solo spot on a Playboy cover in 1971, following Jean Bell’s 1970 cover with four other models. 


Dolly Parton graced Playboy’s front in the now instantly recognizable bow tie/bunny ears combo and kept her clothes on on the inside pages.


This controversial issue featured a ten-page spread titled, “The Women of the U.S. Government.” It ran days before Ronald Reagan was elected president and caused a bit of a stir in the political world. Two Naval enlistees featured in the spread were honorably discharged after its publication. 


Latoya Jackson posed topless in her pictorial, and said it was “to show my parents they couldn’t dictate me anymore—that I control my life.” At the time of its release, the issue sold over 8 million copies, making it the highest-selling issue of the magazine ever.


Back when Donald Trump’s comb-over was one layer thicker, he let loose on Playboy’s cover. Just kidding, he doesn’t do that. The design team threw Playmate Brandi Brandt in there to liven things up a little, but really, it’s like using glitter to make roadkill look alive. Maybe I’m being too harsh: from the looks of it, Trump may have had a stomach ache that day.


Inspired by the 1971 Darine Stern cover, Marge Simpson’s Playboy appearance made a lot of dreams come true. Inside the issue were images of the cartoon (now with nipples!) in see-through lingerie, garter belts and cradling a sexy plate of donuts.


In what could be a nod back to the first Playboy cover, Lindsay Lohan channels Marilyn Monroe. Cyclical imagery, y’all.