The 15 Most Iconic Playboy Covers of All Time

By Isabel Jones
Updated: Sep 29, 2017 @ 3:38 pm
Playboy Archive

Whether you count the late Hugh Hefner as a style icon, a sexual freedom pioneer, a pompous chauvinist, or a little of all three, there's no doubt the founder of Playboy Magazine has had a resounding impact on the fashion and pop culture landscapes.

To remember the entrepreneur, who passed away yesterday at the age of 91, we've taken a look back at the 15 most iconic covers in Playboy history.

VIDEO: Obit From Playboy: Hugh Hefner Dies at 91

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1 of 16

Marilyn Monroe (December 1953)

Courtesy of Playboy

Behold, the first EVER issue of the magazine. Not a bad way to kick off a publishing legacy, if you ask us!

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2 of 16

Darine Stern (October 1971)

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In 1971, Playboy made history by featuring its first-ever African American cover girl. 

3 of 16

Barbra Streisand (October 1977)

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The legendary singer shocked both readers and fans when she appeared on the cover of the risqué 'zine. "What's a nice Jewish girl like me doing on the cover of Playboy?" the cover teased. 

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4 of 16

Farrah Fawcett (December 1978)

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The iconic Charlie's angel rocked her signature shag and blinding smile on the magazine's December 1978 cover. 

5 of 16

Madonna (Septmeber 1985)

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The O.G. material girl cast off her belongings for a nude shoot with the famous men's mag. 

6 of 16

Pamela Anderson (October 1989)

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The longtime playmate put a NSFW twist on back-to-school on the cover of Playboy's October 1989 issue.  

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7 of 16

Donald Trump (March 1990)

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Are you even surprised? 

8 of 16

Anna Nicole Smith (June 1993)

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The late Anna Nicole channeled Playboy's inaugural cover star as "Playmate of the Year" in 1993. 

9 of 16

Jerry Seinfeld (October 1993)

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The comedian is one of the few men to ever grace Playboy's cover. To this day, the issue remains one of the most valuable in the magazine's history. 

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10 of 16

Drew Barrymore (January 1995)

Playboy Archive

The child star caused quite the stir when she posed for Playboy at just 19 years old. 

11 of 16

Cindy Crawford (October 1998)

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The supermodel stripped down to just a tiny sarong for the pink and purple-hued cover. 

12 of 16

Naomi Campbell (December 1999)

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Campbell phoned it in for her Playboy Christmas cover—just kidding, but she *was* holding a phone (pre-cell, remember?). 

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13 of 16

Kim Kardashian (Pre-West) (December 2007)

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In the early days of her reign, "Hollywood's New Sex Star" posed for a cover.

14 of 16

Marge Simpson (2009)

Playboy

The blue-haired Simpsons character stripped down for Playboy in 2009, recreating Darine Stern's 1971 cover. 

15 of 16

Kate Moss (January/February 2014)

Playboy Archive

For the magazine's 60-year anniversary, Moss dressed the part as a classic Playboy bunny in a strapless leotard, bunny ears, a white shirt cuffs and collar, and some seriously badass black pumps. 

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