As the man in the pajamas thumbed through his old address books for the first time in 40 years, the names inside were not just any old names: Richard Avedon, Oleg Cassini, Nat King Cole, Rona Jaffe.

Then he came across an entry that really set the wheels of memory turning. It said, “Big blonde from `Wild Women of Wongo.’ ”

He smiled and explained: “A no-budget movie made in Miami.”

And the blonde?

“No idea,” he said wistfully, chin jutting out like the prow of a ship. “I apparently never got her number.”

As great regrets go, it does not exactly rank alongside Dante’s failure to hook up with Beatrice. And as great documents, the ones that sat on a table the other day at the Pierre Hotel were not quite first-edition Fitzgeralds.

But since they once belonged to the man in the pajamas, Hugh Marston Hefner, these were not just any old address books. They were the little black books of the man who practically invented the little black book – along with, of course, a whole new fantasy aesthetic for the modern male and a magazine that, at 50 this year, remains the best-selling men’s magazine in the world.

The weathered palm-size volumes, once handy for a quick date on a slow Chicago Saturday night, have passed fully into the realm of historical relic. And so, to some extent, has the man who once kept them, a fact he acknowledged with a mixture of pride, humor and a touch of sadness.

“Imagine my disappointment,” he said, emerging from the bedroom of his sprawling hotel suite the other day, clutching the books, “when I call these numbers now and there’s nobody home.”

Next Wednesday, someone is likely to pay more than $10,000 apiece for those lists of faded names and disconnected numbers, at an auction at Christie’s of more than 300 manuscripts, letters, photographs, cartoons, pieces of art and other memorabilia (if you can call a black Mercedes stretch limousine memorabilia) from the archives of Playboy magazine, which Mr. Hefner founded in his Chicago apartment in 1953.

Part of the magazine’s anniversary celebration, the auction presents a half-clothed collage of high and low American culture over the last half of the 20th century: letters from Frank Sinatra, Ayn Rand, Timothy Leary, Barry Goldwater; Little Annie Fanny cartoons; an original Jack Kerouac typed manuscript, with his handwritten corrections; a nude swimming-pool shot of Sophia Loren; a butterfly sketch by Vladimir Nabokov; a moody oil painting of Telly Savalas looking like a pinstriped Buddha. (The items will be on public display at 20 Rockefeller Plaza from Saturday through Tuesday.)

But the auction lots also hold a fair number of Mr. Hefner’s personal effects. And when a Christie’s official suggested carrying a carton or two to the Pierre recently, for Mr. Hefner to dig through like Dad in the basement – or more precisely, like Daddy-o, with a reporter present to record the event, of course – he readily agreed.

It was about 1:30 in the afternoon, and Mr. Hefner, 77, looking a little sleepy and nursing a cold, was decked out dutifully in the uniform his public has come to expect: black silk pajamas, black slippers, burgundy smoking jacket. In the middle of a sea of attendants – publicists, bodyguards, archivists, photographers and two young blond girlfriends who departed early, talking about their outfits – Mr. Hefner seemed to be the only serene person in the room.

First, he admired a cartoon he had drawn himself, in the early years of the magazine, showing two art-school geeks looking at an abstract painting, one of them commenting to the other: “Man – is she stacked.”

“That says it all,” Mr. Hefner pronounced.

(Asked if he ever regretted not remaining a cartoonist, he and several other people in the room burst into laughter. “I know what the life of a cartoonist is like,” he answered, “and I know what my life is like.”)

Mr. Hefner also discussed the provenance of a handful of old letters – one from an embattled Lenny Bruce, asking for help to “keep my curls above water”; another from Fred Astaire, protesting politely that a photo of him with a glass of Champagne had appeared in the magazine. (“I really do not happen to like Champagne,” he wrote.)

But mostly Mr. Hefner kept coming back to his little black books, which he carried from 1956 into the early 1960’s and which read like an alphabetized, shorthand chronicle of his life in those heady years, as the magazine was gaining notoriety and a huge readership, and Playboy clubs were beginning to open around the country.

There were names and numbers of early influences, like Peter Arno, the cartoonist, and Samson Raphaelson, who wrote the 1925 play “The Jazz Singer” and who was one of Mr. Hefner’s instructors at the University of Illinois. Those names led to a long conversation that ranged from Ernst Lubitsch to Picasso to the Art Institute of Chicago, which naturally led to the subject of – what else? – nakedness.

“Indeed, the first nude I ever saw in the daylight was in a class at the art institute,” he said, adding with pride that when he finally left Chicago for the West Coast, he donated the Playboy mansion to the institute, which called it Hefner Hall.

There were numbers for clubs and hotels that had closed long ago, including many of his own. One scribbled note among the pages said, somewhat evocatively, “Latin Quarter bird.” And then another mentioned the same legendary Times Square nightclub, which was once owned by Barbara Walters’s father.

“I must have been hanging out at the Latin Quarter,” he said, staring out his suite’s window into Central Park and trying to conjure up the past.

Among numbers for Joni and Connie and Bonnie, there was also one for Colleen Farrington, the mother of the actress Diane Lane and a Playmate in the late 1950’s. “Ah, yes, I remember her,” Mr. Hefner said.

Another note, more cryptic, said simply: “Late night hock.” He was not exactly sure what he had meant by that, but he smiled broadly and guessed, “Sounds like sex in the middle of the night to me.”

But among these reminders of fame and endless fun there were names of many people who were no longer in his life, of girlfriends and friends who had been taken by cancer and others who had died of various causes through the years.

“It’s like `The Twilight Zone,’ ” he said at one point, and when asked how he felt that the books would soon be bought by the highest bidder, Mr. Hefner suddenly grew somber.

“To be perfectly frank, if they weren’t already up for auction, I wouldn’t sell them,” he said, explaining that he was not quite sure where they had been since the early 1960’s or how they had ended up in the sale.

But as the interview ended and the Christie’s archivists swooped in to collect all of the expensive items spread on the table, the little black books went with them, too.

And when Mr. Hefner, who had gone back into his bedroom, reappeared, he was chipper once again. He was holding a plastic keychain in the shape of the cartoon character Gumby, arrayed in a sexy pose. Underneath the character were the words: “Gumby. Claymate of the Year.”

Mr. Hefner looked ecstatic and announced to everyone:

“We’ve come a long way, baby!”