Lawrence Schiller and William Woodfield, Marilyn Monroe, 'Marilyn Monroe Remembered', January 1964

Iconic pictures of Playmates Elle Macpherson, Cindy Crawford, Bo Derek, and Marilyn Monroe were among 85 lots that went under the hammer for a total of $2,903,438 in New York. The top seller was Tom Wesselmann’s ‘Mouth’ – a pop art image of a smiling, lipsticked mouth, which sold for $1,874,500. The huge cut-out mouth painting was commissioned by the adult magazine in 1966 and intended to be glossy yet sexually inviting, according to the artist. Dozens of photos of naked supermodels with Hefner’s initials on some of the layouts he signed off also sparked a bidding frenzy. Sexy shots of screen siren Marilyn Monroe taking a swim nude and then toweling herself off in 1964 raised $25,000.

A 1958 cover photo of topless Brigitte Bardot went for $23,750, while 1991 photos of Stephanie Seymour frolicking in the sea made $22,500. Cindy Crawford holding her breasts and other 1988 prints of the American supermodel by photographer Herb Ritts went for $21,250. Classic 1994 black and white shots of Elle ‘The Body’ MacPherson posing nude fetched $11,717 The Christie’s auction, which marked the magazine’s 50th anniversary, was called The Year of the Rabbit: The Playboy Collection.

Herb Ritts, Cindy Crawford, ‘Skinsuits’, July 1988, Gelatin silver print

In an interview last month from his Los Angeles mansion, founder and editor-in-chief Hugh Hefner said the magazine that has entertained, titillated and informed with its commissioned art has blurred the lines between fine and popular art. “Playboy helped to change the very direction of commercial art — breaking down the wall between fine art and commercial art,” the 84-year-old Hefner said. “Before Playboy and a few other places, commercial art was essentially Norman Rockwell, very realistic. And we introduced into commercial illustration the whole notion of everything from abstract to semiabstract to stuff that you found on a gallery wall.” The sale represented only a fraction of Playboy’s historic art. Baker said the Chicago-based Playboy houses an archive of 5,000 contemporary artworks and more than 20 million photographs in a storage building in the city. Wednesday’s sale marked 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. Prices included the buyers premium.

Herb Ritts, Stephanie Seymour, March 1991, Gelatin silver print

Photographer Unknown, Brigitte Bardot, cover, March 1958, Gelatin silver print, Sitter credit and sate in pencil (on the verso), 11 ¾ in. x 9 in.