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. 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. 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. 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. 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.

The advertising regions were, Chicago Metropolitan, New York Metropolitan, Southern California, Northern California, Central, Eastern, Western, Southeastern, Southwestern, Canada, International, United Kingdom and Military. 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.