The Greatest Playboy Covers of All Time

It’s not like you need anyone to tell you Playboy cover models are hot, because Playboy models are the go-to for all-time sexiness. After all, Playboy’s first cover model was Marilyn Monroe — and that pretty much set the tone for decades of bombshells to come.

But knowing something to be true in your heart and seeing it in the for reals are not the same thing, right. Playboy’s got a new book out – Playboy’s Greatest Covers is an exciting new release that features the stunning women who’ve graced these covers. From Marilyn Monroe to Dita von Teese, from Dolly Parton to Madonna, Playboy’s Greatest Covers contains the women who have enticed millions from the fifties to the new millennium.

Picked by Hugh Hefner himself, the book features 200 of Playboy’s breathtaking, innovative covers for this 350-page hardcover.

Acclaimed author and longtime Playboy writer, Damon Brown, explores how the magazine’s newsstand decisions made an indelible impact on American culture, while ultimate Playmate, Pamela Anderson, writes the foreword.

TSJ caught up with Damon Brown to talk about what it’s like to make a Playboy book.

The Smoking Jacket: So uhhhh best job ever? What do you think of this most awesome coffee table book?

Damon Brown: Coffee table books usually fall into two categories: Erudite art books and racy photo catalogs. I’m proud of the Playboy book because, like the magazine, it carefully straddles the line between high art and hot pictures. It is also respectable enough to sit on any adult’s coffee table. It took several years to decide on the best covers and investigate the history, but it was definitely fun!

TSJ: How does this book serve to uphold the Playboy legacy?

DB: It’s only right that a Playboy book have equally important words and pictures, so my goal was to tell a story both verbally and visually.

What I found was that each of the 200-plus covers featured in the book reveals a deeper history about not only Playboy, but America itself.

You can flip through the book and see pop culture unfolding — a testament to Playboy’s relevance and accuracy.

TSJ: What are some of your fave covers? Is there a particular era you like? A particular model? Photographer?

DB: I absolutely love the ’60s era, and this is for a few different reasons. First, Playboy really captures the late Rat Pack era, where guys wore suits onto airplanes and women dressed to the nines for dinner parties. Second, it shows Playboy’s evolution from a men’s peep magazine to a men’s lifestyle guide. Finally, the visual aesthetic is sensual and dark, really pulling you into the fantasy — you can almost picture seeing the women across the room in a smoky underground nightclub.

Some of my favorite covers are from the ’60s and ’70s era. I’m partial to the April 1963 cover of a Playboy bunny serving drinks at the first New York Playboy club. The November 1970 cover is great, too, with the top-down view of the model and her flowing hair. From a historical standpoint, the October 1971 cover is phenomenal for featuring one of the first African-American models on a major magazine – and she’s absolutely gorgeous at that.

TSJ: How would you describe the evolution of the Playboy cover over the years?

DB: It’s easy to believe that the Playboy we love today is exactly the same way it was in, say, the ’80s or even the ’60s, but that’s simply not true. For instance, repeated Playmate promotion didn’t go into full swing until Anna Nicole Smith, Jenny McCarthy, and Pamela Anderson (who wrote the foreword to the book) arrived in the ’90s.

Check out the ’70s covers and you’ll see that Playboy was risqué as hell, pushing the boundaries of what you could show on the newsstands.

As I discussed in my previous book Porn & Pong, the beauty of Playboy is how it both creates and reflects modern culture. It just happens to use gorgeous women to do it.

Get Playboy’s Greatest Covers here.

Related on The Smoking Jacket:
4 Classic Moments from Hef’s “Playboy After Dark”
Happy Birthday Marilyn Monroe!

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