NEW YORK (CNN/Money) - As Playboy approaches its 50th anniversary, Christie's International is looking to mine some gold from the auction of cartoons, manuscripts and photographs from the magazine's archives.

"In order to best represent the magazine's history and collection," reads a description of the auction on Christie's Web site, "the sale will also feature a carefully selected group of adult themes and nudity, the core of Playboy's identity."

Paintings like this one by Alberto Vargas, to be auctioned at Christie's in New York, have sold for about $30,000.

Items to be auctioned will include cartoons by Shel Silverstein and painted "Vargas girls" by artist Alberto Vargas. Photographs by the likes of Helmut Newton and Herb Ritts will also be auctioned.

A Mercedes limousine owned by Playboy founder Hugh Hefner will also be auctioned. The winning bidder for that automobile will taken to the Playboy mansion and receive keys to the car from Hefner. An expected sale price for the limousine has not yet been released by Christie's.

This photo of Marilyn Monroe, which appeared in the December 1960 Playboy, will be auctioned at Christie's. It is expected to sell for $3,000 to $5,000.

Highlights from the collection begin a national tour on Wednesday. The tour will begin in New York, where items will be on display until Aug. 8. From there, the items will travel to Pebble Beach, Calif., Los Angeles, Las Vegas and Chicago before returning to New York. The auction will take place in New York City on Dec. 17. Pre-sale on-line bidding will begin in early November at www.christies.com.

Among the items to be auctioned are advance proofs of Parts I-III of the first U.S. edition of Ian Fleming's James Bond novel, "On Her Majesty's Secret Service." The novel's first U.S. publication was in Playboy's May and June 1963 issues. Christie's estimates that the proofs will get between $18,000 and $24,000 at auction.

A 33-page typed manuscript of Jack Kerouac's novelette "Before the Road" is expected to sell for between $20,000 and $30,000. The manuscript contains corrections in Kerouac's handwriting and is signed by the author.

An original Playboy Bunny costume is predicted to go for between $4,000 and $6,000. Two of Hugh Hefner's small address books -- actually "little black books" -- from 1957 and 1958 are expected to sell for $8,000 to $12,000. Addresses and phone numbers include those for Richard Avedon, Oleg Cassini, and artist Leroy Neiman.

"Man is she stacked" was the caption for this cartoon by Hugh Hefner, which appeared in the first issue of Playboy.

Photographs to be auctioned include portraits of Elizabeth Taylor, Cindy Crawford, Marilyn Monroe, Madonna and Brigitte Bardot. The photographers featured include Helmut Newton, Herb Ritts and Lee Friedlander.

A cartoon by Hugh Hefner himself, captioned "Man is she stacked" and used in the first edition of the magazine, is expected to sell for $2,000 to $3,000. Several "Little Annie Fanny" cartoons will also be auctioned. One, "Little Annie Fanny: James Bomb," which appeared in the December 1967 issue, is expected to sell for $20,000 to $30,000.

In an auction of Playboy (PLA: Research, Estimates) items held in Los Angeles on June 23, 2002, a bidder paid $32,000 for an original Vargas Girl watercolor. That painting featured a girl dressed in a Batman costume and featured the caption "How do you like my dynamic duo?" Two other Vargas Girl paintings also sold for about $30,000. That auction was held by Butterfields, now called Bonhams & Butterfields.

A 1962 Leroy Nieman painting, "After the August 1962 Cover," sold for $19,250 at that auction and another, "Man at His Leisure (Surfing)," completed in July, 1967, sold for $29,125.