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  There are a few magazines where the cover has, on a regular basis, achieved iconic status, Rolling Stone, National Geographi, LIFE and of course Playboy.
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Cover Story
Hugh Hefner took a bold gamble when he started a new magazine. Though, with Marilyn Monroe on the cover and that image inside perhaps not so much. To celebrate that union artist Rob Silvers was recruited to create the 45th Anniversary cover of the January 1999 issue using nearly five decades of past PLAYBOY covers.
The full size poster version shows Marilyn's full centerfold pose. A cropped version of the collage is used on the cover and consists of 1024 images. If this was laid out using actual magazines it would be approximately 6.688x8.864 meters (21.94x29.08 feet).
Silvers, who designed the computer program that performs this magic, used unaltered PLAYBOY covers to generate the image. Look closely and you can identify nearly every month from the 45 years. At a distance, Marilyn appears, and reminds us how it all began.
I've put together a cropped version of the Marilyn collage, in a variety of sizes, to fit computer screens as desktop wallpaper. This is not merely a scan of the cover or indeed even the poster but is made up of individual cover images. You can download it here.
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International Distribution
From 1955 up until the September 1979 issue (except for a six-month period in 1976) the cover carried an arrangement of stars next to the P in Playboy. Sometimes they appeared within the P itself but anyway they indicated the different advertising regions of which there were 13 at it's peak. Not, as some have speculated, Hef's rating of the Playmate.
What this meant was that an insert of pages, at least 4, but I've seen as many as 16 extra pages were added to the magazine in a targeted marketing approach. So copies that were originally destined for different areas may have different adverts.
The advertising regions were, Chicago Metropolitan, New York Metropolitan,  Southern California, Northern California, Central, Eastern, Western,  Southeastern, Southwestern, Canada, International, United Kingdom and Military.
Award Winning
Richard Fegley photographed Darine Stern in Art Director Len Willis's rabbit head chair for the October 1971 issue. In October of 2005 the American Institute of Magazine Editors (ASME) choose it as one of the best magazine covers of the previous 40 years.

A Rare Lack Of Color
Of all of the covers over the years there are few that rely solely on a black & white image. That is with no other graphics constituting the cover except content highlights. There's the first issue's cover, those of May 1973, July 1988, January 2007 although the earlier two both have a slight sepia tint and the June 1993 cover of Anna Nicole Smith photographed by Daniela Federici.

Repeat Performance
Pamela Anderson made her Playboy debut on the October 1989 cover and would go on to do so again for a total of fifteen times; more Playboy covers than anyone else.