Published: Saturday, 24 Oct 2009 | 9:23 AM ET

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Hugh Hefner leaned back on a red loveseat, the saggy one in the study of his infamous mansion here, and interlocked his fingers behind his head. A visitor had asked — more like shouted, since he has trouble hearing — a question about mortality.

At 83, does he think about it?

In a word, no. Mr. Hefner, the legendarily libidinous founder of Playboy, the prophet of hedonism, does not believe that his denouement is at hand.

He doesn’t act like it, either. He still works full days on his magazine, flies to Europe and Las Vegas, pops Viagra, visits nightclubs with his three live-in girlfriends — each young enough to be his great-granddaughter — and is working with the producer Brian Grazer on a film.

“This is one of the very best times of my life,” he said, grinning, dressed in pajamas and slippers. “It’s even better, richer than people know.”

You want to believe him, but it is hard to ignore the realities of his business. Playboy Enterprises

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[  Loading...      ()   ], hobbled by a shifting media landscape, is in need of heart paddles. On Tuesday, the magazine said it would cut the circulation numbers it guarantees to advertisers to 1.5 million, from 2.6 million. The company has lost money for seven quarters in a row.

And perhaps most shockingly, the company said earlier this year that it would consider acquisition offers, something that was believed to be unthinkable while Mr. Hefner was still alive.

Mr. Hefner knows every good party must end, having long ago bought a crypt next to Marilyn Monroe at a Los Angeles cemetery. In interviews over the years, he has talked about how life wouldn’t be worth living without Playboy. “If I sold it, my life would be over,” he has said. But he may be coming around: “I’m taking more seriously the fact that I’m not 30 years old anymore. I need to think about the continuity of the magazine.”

Love him or loathe him, no one doubts Mr. Hefner’s influence in American cultural history. As a magazine publisher, he essentially did for sex what Ray Kroc did for roadside food: clean it up for a rising middle class.

As a cultural force, however, Mr. Hefner still divides the country — 56 years after Playboy’s first issue. To his supporters, he is the great sexual liberator who helped free Americans from Puritanism and neurosis. To his detractors, including many feminists and social conservatives, he helped set in motion a revolution in sexual attitudes that have objectified and victimized countless women and promoted an immoral, whatever-feels-good approach to life.

Mr. Hefner will concede that there are dark consequences of what he helped set into motion, but said “it’s a small price to pay for personal freedom.”

“People don’t always make good decisions. The real obscenities on this planet have very little to do with sex,” he said, adding that “it’s not as romantic a time.”

Less romantic and — with instantly available pornography online and graphic sex talk, including on Mr. Hefner’s own show, “The Girls Next Door,” on TV — it’s a time that makes Playboy’s ideals seem quaint. Mr. Hefner — who uses the word “cat” to describe himself, as in, “I’m the luckiest cat on the planet” — doesn’t think much of today’s cultural landscape.

“I feel strongly that the pop culture is a thinner soup today,” he said. “It used to be a thick porridge.”

At the same time, he tries to be an active participant. While the magazine is still edited largely in Chicago, Mr. Hefner approves “every Playmate, every cover, the cartoons and the letters.” Working from a home office or his bed, where the 1970s-era Tasmanian opossum fur bedspread has been traded for a silk and velvet one, Mr. Hefner helped drive the recent decision to buy a 5,000-word excerpt of Vladimir Nabokov’s unfinished novella, “The Original of Laura,” for a forthcoming issue.

His girlfriends recently educated him about Twitter. (“I’ll be playing gin rummy tonight” was a recent tweet.) He’s hooked on the HBO drama “True Blood.” He recently filmed a Guitar Hero commercial, holding the pipe he gave up after a suffering a small stroke in 1985. He has also suffered personal humiliations. Former live-in girlfriends, including those who have appeared on “The Girls Next Door,” have portrayed him in interviews and a book as a control freak who enforces a curfew of 9 p.m. The mansion itself has seen better days. During a July visit, the game house (the one with a room that has a mattress as flooring) smelled musty, while the bird aviary needed scrubbing. That famous grotto, with its Jacuzzis of varied depth, seemed more like a fetid zoo exhibit than a pleasure palace (although nearby shelves were stocked with enormous bottles of Johnson’s Baby Oil).

In March, with the housing market in a nosedive, he put his wife’s home, located next door to the Playboy Mansion, up for sale for $28 million. It sold in August for $18 million. Mr. Hefner, who separated from Kimberly Conrad Hefner in 1998, filed for divorce in early September; she is suing him, claiming he owes her $4 million under a prenuptial agreement and proceeds from the home’s sale.

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Mr. Hefner’s retinue insists that money is not tight, but a series of actions has made it look that way. The Los Angeles Business Journal reported last year that the mansion’s staff had been cut. People can now buy tickets (up to $10,000 each) to what were once invitation-only parties, which remain a vital part of stoking the Playboy brand.

“It’s not always as exciting as people think,” said Holly Madison in an interview last summer. Ms. Madison lived with Mr. Hefner for seven years as his “No. 1 girlfriend” until she broke up with him last fall.

Richard Rosenzweig, who has worked at Playboy since 1958 and holds multiple titles, begged to differ. “This is a very aspirational place,” he said in an interview in Mr. Hefner’s dining room. “Everybody wants to come here.”

When Mr. Hefner’s relationship with Ms. Madison ended, he said he got letters from women around the world begging to move in. “They were climbing over the gates,” he said, beaming. Mr. Hefner chose three new live-in girlfriends, 23-year-old Crystal Harris and twins Kristina and Karissa Shannon, 20.

Despite his chipper attitude, Mr. Hefner clearly has legacy on his mind. Lately, he has been poring over his scrapbooks, which he has been keeping since childhood and now number over 2,000. Never-before-seen material from them — his first library card, self-drawn comic strips and pictures — will form the heart of a 3,506-page, six-volume “illustrated biography” from Taschen. Only 1,500 of the $1,300 behemoths will be sold, starting next month.

For the first time, Mr. Hefner has also given unfettered access to a documentary filmmaker, Brigitte Berman, whose recently completed “Hugh Hefner: Playboy, Activist and Rebel” made its premiere at the Toronto International Film Festival.

And a major Hollywood biopic is speeding ahead at long last. Mr. Grazer recently met with the screenwriter Diablo Cody about the project, Mr. Hefner said. Brett Ratner (best known for the “Rush Hour” blockbusters) is lined up to direct. Robert Downey Jr. has expressed interest in playing Mr. Hefner.

“He’s an intellect of the highest order who influenced the worldwide zeitgeist in a grand way — and that influence is drastically underrated,” Mr. Grazer said.

Indeed, some of his long-time friends fret that some of the accomplishments they admire — creating a cultural icon (the Playboy Bunny), eroding racial boundaries (through the inclusion of black performers in his clubs), and supporting many feminist causes, including abortion rights and the Equal Rights Amendment — are getting lost.

Mr. Hefner worries about it, too. “We just literally live in a very different world and I played a part in making it that way,” he said. “Young people have no idea about that.”

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