Playboy Collectibles Up for Auction in December has enjoyed a long relationship with Playboy Enterprises, from being a rich resource of playmates and cyber girls to having some of the magazine’s top photographers and models shooting in the OMP Studio. Now Playboy is working with auction experts Christie’s to auction off more than 125 works from the corporate collection of Playboy Enterprises in Chicago on December 8.

According to the report on, Hefner is also reportedly looking to sell the Playboy Mansion, with mounting debts and buyout bids threatening the company’s future. The sale of Playboy art is speculated to be part of Hefner’s need to raise cash.

Pictured: Portrait of Hugh Hefner

Estimated value: $5,000-7,000
Artist: Herb Davidson
Oil on canvas, painted in 1970

Although never featured in Playboy magazine, this 1970 portrait by Herb Davidson depicts Hefner in his signature smoking jacket. The work measures 24 by 18 inches and is expected to bring between $5,000 and $7,000 by Christie’s.

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