(AP): Nearly all the items in the sale have appeared in the publication, a cultural icon that helped liberate American sexual mores.
A Stephen Wayda 1996 cover photograph of Playmate of the Year Stacy Sanchez draped in white fabric in the shape of Playboy's bunny logo is initialed by Hugh Hefner and contains editorial comments like "move leg to this position" and "missing eye shadow."
"It's the tip of the iceberg," said Aaron Baker, curator of the Playboy Art Collection for the last eight years. Chicago-based Playboy houses an archive of 5,000 contemporary artworks and more than 20 million photographs in a storage building in the city.
The boards "really take you behind the scenes and show the editorial process," Baker said.
The sale has a number of Marilyn Monroe images, including a photograph that was used for the cover of Playboy's December 1953 premiere issue. The magazine purchased it from United Press, shot during a parade of M
onroe riding on the back of a car. Playboy swapped out the background of a crowd for its own logo.
It shows Monroe with her arm raised "almost as if she was waving to the readers, inviting them into the pages of the book of these incredible nude shots of her that they had never seen before," Baker said.
Playmate of the Year Stacy Sanchez poses in a fabric bunny in Stephen Wayda's 1996 cover photograph. Mounted, initialed by Hugh Hefner.
AP Photo/CHRISTIE'S IMAGES LTD., Stephen Wayda)
This image of Brigette Bardot appeared on the March 1958 cover of Playboy.
AP Photo/CHRISTIE'S IMAGES LTD
Coneheads! A 1993 Stephen Wayda photograph.
AP Photo/CHRISTIE'S IMAGES LTD., Stephen Wayda
This original watercolor by Alberto Vargas appeared in the November 1969 issue of Playboy.
AP Photo/Heritage Auction Galleries
The immortal founder of Playboy poses in his signature robe and mansion.
AP Photo/Jae C. Hong
Patrick Nagel painted this pin-up, which appeared in the August 1980 issue of Playboy.
AP Photo /Heritage Auction Galleries
A Phil Interlandi cartoon from the January 1973 Playboy.
AP Photo/Heritage Auction Galleries)
This was the image that appeared on the FIRST Playboy magazine cover for the December 1953 issue.
AP Photo/CHRISTIE'S IMAGES LTD.
1970 oil painting by Herb Davidson of Hugh Hefner.
AP Photo/CHRISTIE'S IMAGES LTD.)
This 1967 oil painting is by Tom Wesselmann.
AP Photo/CHRISTIE'S IMAGES LTD
by AP/Huffington Post November 9, 2010