Christie’s to sell Playboy at 50: selections from the archives 17th Dec - New York

Fifty years of Playboy magazine and American pop culture will be celebrated at Christie’s on December 17, with the sale Playboy at 50: Selections from the Archives at Rockefeller Center. The more than 300 items from Playboy’s renowned archives – including original manuscripts, cartoons, paintings, celebrity and fashion photographs, and memorabilia – chronicle Playboy’s groundbreaking style and America’s cultural evolution through the connections among fine arts, literature, music, and historical events.

Manuscripts and Illustrations

Throughout its first 50 years, Playboy has featured a remarkable number of important literary contributions, and this historical legacy will be represented in the sale by some of the most significant examples from the archives in each area, from fiction, non-fiction, the Playboy Interview, Dear Playboy, and other related correspondence.

The sale includes numerous original, corrected, typescripts by such important authors as Ian Fleming, James Baldwin, Nelson Algren, Ray Bradbury, Arthur C. Clarke, Kurt Vonnegut Jr., Jack Kerouac, Allen Ginsberg, and Alex Haley. An original, 33-page typed manuscript of Jack Kerouac’s novelette Before the Road describes the early days of Dean Moriarty, the literary personification of Kerouac’s friend Neal Cassady from the legendary On the Road (estimate: $20,000-30,000). The manuscript features numerous corrections in Kerouac's hand and is signed at the end by the author. Ian Fleming’s On Her Majesty’s Secret Service was first published in Playboy in May and June of 1963. Included in the sale are the advance proofs of parts I through III of the first English edition, which are divided and marked with corrections and insertions by the author (estimate: $18,000-24,000).

From its inception, Playboy has been recognized throughout the world for publishing groundbreaking interviews with the most famous, infamous, and admired figures from the worlds of entertainment, sports, politics, the arts, and literature. Playboy at 50 includes galley sheets – often heavily revised and signed by the interviewee – of dialogues with such notable figures as Ayn Rand, Salvador Dalí, Henry Miller, Vladimir Nabokov, Bertrand Russell, Jean-Paul Sartre, Muhammad Ali, the Beatles, and Bob Dylan. In addition, the sale includes many letters from the pages of Dear Playboy and other correspondence to Hugh Hefner himself from Woody Allen, Joan Crawford, Bobby Darin, Allen Ginsberg, Tippi Hedren, Robert Heinlein, Vladimir Nabokov, and Frank Sinatra.

Hugh Hefner started out his career as a cartoonist and among the most exciting aspects of the Playboy collection is the large and important body of illustration art and cartoons, including memorable images by such renowned cartoonists as Shel Silverstein, Jack Cole, Eldon Dedini, Phil Interlandi, Erich Sokol, and Gahan Wilson. Also included are examples from Playboy’s masterful “Little Annie Fanny” series by Kurtzman and Elder. Highlights include “Little Annie Fanny: James Bomb,” from the December 1967 issue (estimate: $20,000-30,000), and “Kennedy Jokes with Monroe,” from the May 1963 issue (estimate: $7,000-9,000). Mr. Hefner is represented in this section by “Man is She Stacked,” a cartoon from the very first issue of Playboy (estimate: $2,000-3,000).

Fine Art and Photographs

Christie’s to sell Playboy at 50: selections from the archives 17th Dec - New York Playboy at 50 offers a selection of paintings, drawings, and sculpture from America’s post-war period by Tom Wesselmann, LeRoy Neiman, Ed Pashke, Roger Brown, Patrick Nagel and other artists who are instantly recognizable to Playboy readers and art collectors alike. The majority of the works were commissioned to illustrate articles and short stories in the magazine. Hugh Hefner and Art Director Art Paul gave the artists rare carte blanche to contribute their own interpretations of subjects, who were often famous musicians, professional athletes, entertainers, and political figures featured in the magazine. Works by LeRoy Neiman, a prolific contributor to the magazine since its inception, include portraits such as Bird (Charlie Parker), 1957 (estimate: $10,000-15,000) and works from the “Man at His Leisure” series, such as Le Mans, 1969, (estimate: $20,000-30,000). Additional Neiman highlights include selected original drawings from his recurring ‘Femlin’ series. The sale also will include works that previously adorned Playboy Clubs around the world.

Photography has played an essential role in the success and longevity of Playboy, due in part to Hugh Hefner’s visionary selection of artists. The Playboy photograph archive includes the works of some of the most recognized and celebrated contemporary and fashion photographers of our day, among them Helmut Newton, Herb Ritts, Brett Weston, and Lee Friedlander. While erotically charged, their photographs were tasteful and often revolutionary, and many grew to become icons of the period. Playboy at 50 includes a selection of more than 70 images, including celebrity portraits of Marilyn Monroe, Brigitte Bardot, Madonna, and others. Highlights include some of the magazine’s most well-known and frequently reproduced images, such as John Derek’s photograph of Bo Derek (estimate: $5,000-7,000), which appeared on the March 1980 cover, and Herb Ritts’ shots of Cindy Crawford (July 1988) and Elle MacPherson (May 1994), ranging in estimate from $2,000-3,000 to $4,000-6,000. Images from Playboy magazine’s early years include Elizabeth Taylor as Cleopatra, pin-up shots of celebrities, and jazz musicians of the 1950s.


A major highlight of Playboy at 50: Selections from the Archives is Hugh Hefner’s own 1988 Mercedes-Benz 560SEL Stretch Limousine (estimate: $30,000-50,000). Purchased new by Playboy Enterprises Inc. and then converted by Allen Coachworks/Coachworld Limited of Inglewood, CA in 1989 to a full 52-inch stretch limousine for Hugh Hefner, the car’s features include a power moonroof, Sony standard audio/video, Magnavox video cassette player, original leather benchseat, original carpets, Halo lighting, intercom, illuminated ice storage, illuminated vanity mirrors, suspension upgrade and tires upgrade. The successful purchaser of Mr. Hefner's customized limousine will have the exclusive opportunity of picking it up at the Playboy Mansion, photo ops with the limousine in front of the Playboy Mansion, a private tour of the Playboy Mansion - and two tickets to the world-famous, invitation-only New Year's Eve party at the Playboy Mansion on December 31 (airfare and accommodations not included).

Christie’s to sell Playboy at 50: selections from the archives 17th Dec - New York The Bunny and the Bunny Costume are internationally known symbols, and among the memorabilia from Playboy’s first 50 years is an original Playboy Bunny Costume (estimate: $4,000-6,000). Hugh Hefner’s own “Little Black Books”, two small address books from 1957 and 1958, include addresses and phone numbers for such notable early associates as Peter Arno, Richard Avedon, Oleg Cassini, LeRoy Neiman, Bert Stern, and Shel Silverstein (estimate: $8,000-12,000 each).


Christie's catalogue for Playboy at 50: Selections from the Archives is a historical chronology of Playboy's contribution to American culture during the last half-century. A collector’s item itself, the specially designed and richly illustrated catalogue is available by calling 800.395.6300 (from the USA), or via

Photos/Text - Christie's