Manuscripts by James Bond creator Ian Fleming and beat poet Jack Kerouac appear in a forthcoming sale to celebrate the 50th anniversary of Playboy magazine.
Ian Fleming's first draft of On Her Majesty's Secret Service features in the sale
Photography, memorabilia and art from contributors including LeRoy Neiman, Alberto Vargas and Gahan Wilson, as well as a Mercedes once owned by the magazine's flamboyant publisher, Hugh Hefner.
Advanced proofs from the Bond novel On Her Majesty's Secret Service, which include Fleming's notes and annotations, are expected to fetch between $18,000 (£11,500) to $24,000 (£15,380).
Other works, including some by beat poet Allen Ginsberg and writers Henry Miller, Vladimir Nabokov, Jean Paul Sartre and Hunter S Thompson are also included.
There are also letters from actress Joan Crawford, and photos of Playboy's original cover star, Marilyn Monroe.
The auction, at Christie's in New York, will take place on 17 December.
"It will prove there were millions of men who did read it for the articles," joked Mr Hefner on Wednesday.
Mr Hefner started the magazine - the most famous men's publication in the world - in 1954, after buying a picture of Marilyn Monroe and assembling his own magazine on his kitchen table.
Fleming, who created the famous 007 agent in the 1950s, based some of the character on his wartime experiences in naval intelligence.
A first edition of Fleming's Live and Let Die was handed in to a Scottish charity shop last year - and was estimated to be worth £5,000.
A copy of the same book, once owned by Winston Churchill, sold last year for £46,000 at auction.