The sale includes 80 photographs, more than a dozen contemporary works and 24 cartoons.

Among them are a photograph of comedian Dan Aykroyd in a conehead costume with a bunny-suited Anderson, a photo of the magazine's 1953 debut cover of Monroe, an early 1960s shot of sex kitten Brigitte Bardot and three Alberto Vargas pinup girl watercolor and pencil illustration boards. The auction's top draw is expected to be an iconic, sexually charged oil of a scarlet-lipstick mouth by pop artist Tom Wesselmann. Portraits of Duke Ellington and Dennis Hopper and a Herb Ritts photo of Elle Macpherson are also for sale.

"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.

Since "a lot of these are work products," said Cathy Elkies, Christie's head of private and corporate collections, "there's a link between the collection and the ethos of the publication itself."

Nearly all the items in the sale have appeared in the publication, a cultural icon that helped liberate American sexual mores.

Given Hefner's early background as an amateur cartoonist, Elkies said, his connection to art has always been strong.

Among the standout fine art pieces is Dali's "Playmate," a 1966 watercolor of a reclining nude that until recently hung over a mantel in Hefner's bedroom at the Playboy Mansion. It's estimated to bring $100,000 to $150,000. It was one of 11 works chosen for "The Playmate as Fine Art" pictorial for the magazine's January 1967 Playmate review issue that asked artists to create Playmate-inspired art.

"I'm a fan of Dali's and happy to be sharing it," Hefner said, smiling. "It's a reclining nude, so that made it easy to personally identify with it."

The star of the auction, Wesselmann's "Mouth No. 8," depicts the artist's iconic theme of a woman's open, lipsticked mouth. The 1966 work is estimated to bring $2 million to $3 million.

"It's a great example of his work from his best period," Baker said.

Some fun items include a number of layout boards, marked up by Playboy's art directors. Some even contain their penciled ratings of the pinups, for example, "88 out of 100," Elkies said.

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 Hefner and contains editorial comments like "move leg to this position" and "missing eye shadow."

The boards "really take you behind the scenes and show the editorial process," Baker said.

The sale has a number of 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 Monroe 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.

"You know, it becomes a piece of art because it appears on the cover of Playboy," Hefner noted. "One of the things that set Playboy apart from the very beginning was not simply the pretty ladies and the very good literature, but the fact that we were winning art awards in the very first year."

The UP credit appears on the back of the print, which is estimated to fetch $10,000 to $15,000.

An early 1960s print of a demure-looking Bardot in bikini bottoms and hands across her breasts is expected to fetch $4,000 to $6,000. The photographer is unknown.

Original famous centerfolds of Anna Nicole Smith, Jenny McCarthy and Anderson are also included. But not all the material focuses on the erogenous, especially a white plaster cast by George Segal of a pregnant woman seated in a folding chair that was part of the "Playmate of Fine Art" pictorial.

The work is not sensuous, but "for Segal the most beautiful type of woman is one with child," said Baker. The woman is the wife of artist Alfred Leslie, whose work also appeared in the pictorial.

"It's a fun sale ... (that) reflects the spirit of the magazine in a very meaningful and personal way," Elkies said.

Also for sale: a 1970 portrait of Hefner in his signature smoking jacket and pipe. Commissioned for the old Playboy mansion in Chicago in the late 1960s, Playboy Enterprise inherited it after Hefner moved to Los Angeles in the early 1970s. It has a $5,000 to $7,000 estimate.

The December sale marks the second time Christie's has sold items from Playboy. On its 50th anniversary in 2003, Christie's offered memorabilia and ephemera from Playboy's collection.

"This one's really more about the art," said Elkies of the December sale.