Dali's watercolour of a reclining nude, photograph of Dan Aykroyd in a conehead costume or a sexually charged oil of a scarlet-lipstick mouth-these are among 125 pieces of art collection by Playboy that are set to go under the hammer shortly.
Playboy magazine is auctioning off 60 years, which includes 80 photographs, more than a dozen contemporary works and 24 cartoons.
"Playboy helped to change the very direction of commercial art - breaking down the wall between fine art and commercial art," the Sydney Morning Herald quoted Hugh Hefner, Playboy founder, as saying.
Nearly all the items in the sale have appeared in the publication, a cultural icon that helped liberate American sexual mores.
Among them are 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.
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 dollars.
"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 dollars.
The auction would take place in December 8 in Chicago.