Playboy Magazine, December 1999 [Single Issue Magazine] [Dec 01, 1999] Hugh Hefner

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So, in anticipation of the magazine turning over a new leaf, let's look back on 17 of the most iconic Playboy magazine covers from the 1950s to today. To enable personalised advertising (like interest-based ads), we may share your data with our marketing and advertising partners using cookies and other technologies.

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Jayne Kennedy - Miss Ohio 1970 became the first African-American actress to cover Playboy in July 1981. Read more about the condition New: A new, unread, unused book in perfect condition with no missing or damaged pages. Azealia Banks - The ever outspoken Broke With Expensive Taste rapper not only left her label, put out her own album, and sparked online debates about race and sexuality, she also said this of her upcoming Playboy feature: "I'm not going to show my p***y unless I get the cover. So while there were certainly some nude ladies inside the magazine, the cover stars were always a tad more covered up (emphasis on "tad"). Naomi Campbell - Though most readers of Playboy likely hadn't heard of Naomi's cellphone antics (word is she assaulted her assistant with one), it made for a whimsical Girl 6-like cover for the 1999 holiday season.

Wearing nothing but a sheet, Smith's black and white image is very reminiscent of the inaugural Monroe issue. Vanity - The "Nasty Girl" singer, aka Prince's "female reflection," took the cover of Playboy's April 1988, six years before she dropped her stage name for evangelism. An awesome experience, opening the box sent was like activating a magic time-machine: perfect condition, packed with expert care, exactly as described, and arrived super fast. She was discovered at a football game via a jumbo tron close up, and got this cover on the national magazine two months later.

Whether they appeared inside the pages of the magazine or not, many big names, stars, and celebrities have covered the glossy from Marilyn Monroe to Naomi Campbell, to Anna Nicole Smith, to Dolly Parton, and yes, even Kim Kardashian. Over the past 62 years in print, the magazine has produced several iconic covers that have certainly set a high bar. This was her first and last time on the magazine cover, but certainly not the last time we would see someone in Playboy dressed like a bunny, that's for sure.

One of the most recent notable covers goes to Handler, who posed for the magazine in anticipation of her new late night show on E! Anna Nicole Smith, another one of Playboy's major scouts as well as a big-name Playmate of the Year, was on her first cover in 1993.She continued: "So a lot of the parties, people would rent out the mansion if it was related to a charity, so Hef would have his personal parties and then there were rented parties.