Down the Bunny Hole

‘I’ve been feeling like roadkill,' Hugh Hefner told The Independent in the UK a couple of months ago. Until recently, one would have imagined that only being worn out by too much sex with blonde 22-year-olds could make Hef feel this way. But that was before he had his heart broken.

When his 'number-one girlfriend', Holly Madison, left him in October last year nobody was that surprised. This was the woman who had been nagging Hef about marriage and children. If ever there was a case of barking up the wrong 82-year-old tree.... But Hef, it turns out, was serious about Madison. Three years ago, he told The Independent, 'If there is such a thing as a soul mate, that's how I would describe Holly. I expect to spend the rest of my life with her.' He confirms that the two of them tried to conceive a baby early in 2008 but, he says, 'With my sperm count, it's not possible.' After news broke that their relationship was over, all he could ouster was, 'If Holly says it's over, then I guess it's over.' Then, in the same week, Kendra Wilkinson - the girlfriend in the number-three slot jilted Hef too. At the time Bridget Marquardt, who completes the trio was overseas filming a TV show.

If being dumped twice in one week doesn't knock a man all the way down, a failing business will probably finish off the job. And the Playboy empires in bad shape, even after an attempt at brand plastic surgery. What went wrong?

Good Times

In the 70s, Hef called the shots. He chose the cover models for his successful magazine. He decided which girls were staying or leaving. He had sex with pretty much anyone he liked. He was already in his 40s but he could still pull off the 'silk pyjamas' look without looking as though he belonged in a nursing home. Aids had not yet been named, awareness of cocaine's risks was low and all the celebrities partied hard - in every sense of the word - at the mansion.

The hot Playboy lifestyle had a hiatus from 1988 to 1999, while Hef was doing domestic monogamy with Kimberley Conrad. After he left her, he entered what he calls his 'platinum-blonde period'. And the Entertainment channel decided to put it on TV: The Girls Of The Playboy Mansion is into its fifth season. The show follows the daily lives of Hef's three girlfriends, and despite the recent break-ups, the mansion has announced that Madison and Wilkinson will still be there to film season six.

Thanks to El's habit of repeating shows over and over, many a mindless viewing hour can still happily be spent watching the girls go to the mansion salon, snuggle up in bed with Hef to watch movies from the '40s, plan parties, play pranks, go shopping and order the mansion staff around.

Who's your Granddaddy?

What makes it all unsettling is the sex. And it's not the fact that Hef has sex with more than one woman - it's the fact that he has sex at all.

When Hef started dating Barbi Benton in the late '60s, she was 18 and he 42. She told him she had never dated anyone older than 24 and he said, ‘That's all right. Neither have I.’ Which might, in its own horrible chauvinistic way, have been cute then. But not now. The man is 82. He's older than the Pope.

So why do so many hot young women want to sleep with him? For starters, he still personally chooses all of Playboy's covers and Playmate centerfolds. The magazine may be limping along, a victim of the recession, with advertising and readership figures dropping every month, but for as long as it keeps being printed there will be girls hoping to be the next Pamela Anderson. The Playmate selection process is a simple, old-fashioned one. In some years Hef has reportedly slept with eight of the 12 Playmates.

Plus, any girl who gets involved with Hef may end up on the TV show, which opens doors. Madison, whose goal is to visit every Disney theme park in the world, has a clothing line. Marquardt has her own show, Bridget's Beaches, on the Travel Channel. Wilkinson has an exercise empire. All have a constant stream of endorsement deals and movie cameos.

To many women hoping to hit the show-biz big time, getting dirty with the octogenarian may seem worth it. Plus, he's a really nice guy, according to pretty much everyone - from journalists who interview him and businesspeople making deals with him to his exes, most of whom are still his friends. Kimberley Conrad lives next door to the mansion.

On The Girls of The Playboy Mansion Hef comes across as kind and witty. He shuffles around choosing thoughtful gifts, being charming to his girlfriends' mothers and organizing backgammon games. In a sense, he's the thinking woman's Ozzy Osbourne. Which is quite a step down from being the man all other men wanted to be - but it makes for good TV.

Up until season five, Hef, Madison, Marquardt and Wilkinson formed a weird version of a traditional nuclear family. Madison took on a maternal role, organizing outings and making sure Wilkinson wasn't late for them. Marquardt and Wilkinson were the excitable kids, and Hef was the benevolent patriarch who bought everybody cars and told them how proud he was of their achievements - say, looking particularly sexy in a short skirt or arranging a good party.

New Market, New Message

The Playboy Mansion has always been famous for its parties - expensive, debauched events where some seriously dirty stuff goes down. But now, if you were to show up at the old Gothic-Tudor building during the day, there's a fair chance you'd walk in on a birthday party being held for one of the mansion dogs. Oh yes, it happens. The girls buy cakes from a shop that specializes in dog cakes, put up decorations and invite guests who dress up and bring presents from pet boutiques.

The new additions to the mansion's full social calendar show how the Playboy brand has tried to change with the times. Playboy as it was in the 70s is largely irrelevant. Now teenage boys can go online and find girls much more naked than they would in the magazine. Lad magazines such as FHM and Maxim have grabbed market share from Playboy, which seems almost quaint by comparison, with its serious writers in between nude pictorials.

Over the past decade it became clear that the brand needed some new fans and, as it turns out, those new fans are women. In the recent movie The House Bunny, Anna Faris's character Shelley is kicked out of the mansion the day after her 27th birthday for being too old. As she walks out of the door, her old station wagon is waiting for her. 'Where's my pink Prius?' she cries.

That says it all. While once the bunny logo symbolized a fantasy for adolescent men, it has increasingly taken on a Disney-princess sheen and developed an appeal among women. Part of the fantasy is the lifestyle at the mansion. Reports say each girl who stays there gets an allowance of $1 000 a week, a car and unlimited free plastic surgery. They go on day trips to Las Vegas and party with rappers and rock stars. They also get to be a part of the silicone sisterhood living in the mansion. On the show, we see them holding horse-riding parties for one another and helping one another choose fancy-dress outfits. It's fitting that in The House Bunny Shelley finds her niche as a house mother at a university sorority, giving the girls makeovers and lessons in self-confidence.

Is this brand re-angle working? Not really. The Playboy Enterprises share price has fallen to a quarter of what it was a year ago. To make some extra cash, the organization is now selling tickets to mansion parties for up to $25 000. Guests used to be carefully selected for their star status or looks. In fact, that's how both Wilkinson and Marquardt got to be girlfriends: Hef met them at parties and asked them to move in. It's the classic boy-meets-girls story.

Pumping Irony

Once you're in, though, things may not be as you expected. A former girlfriend, Izabella St James, released her book Bunny Tales (Running Press) in 2006. She paints a picture of a gilded cage. Residents of the Playboy Mansion, for example, have a strict 9pm curfew.

There's also a rigid schedule. According to Jill Ann Spaulding, a girlfriend who was thrown out of the mansion and released a tell-all book in 2004, Wednesdays and Fridays were sex nights during her stay. The only excuse for not showing up was being in recovery from plastic surgery. She claims Hef lies on his bed, having popped his Viagra, and each of the girls (girlfriends plus whichever Playmates are staying at the mansion) has sex with him for two minutes while the others cheer her on. Hef insists that all his girls stay faithful to him, yet he is not bound by a similar rule.

Hef, naturally, has a complicated relationship with the feminist movement. On the one hand he has contributed to many women's freedoms. His Playboy foundation gave money to lawsuits that resulted in the legalization of contraception and abortion in the US.

And, as laughable as it is now, he gave women a new career option. In the 60s, for most women the options were housewife, secretary, teacher or nurse. If you were very glam, you were an air hostess. When the Playboy Clubs opened, women could also become Playboy bunnies. To many of those perky, eager-to-please girls, the satin leotards and ears were symbols of freedom. The high salaries they earned bought them independence.

Hef sees women as the biggest beneficiaries of the sexual revolution he helped bring about. Still, he has been criticized for presenting unrealistic images of women who are clearly styled for maximum male appreciation. One of the rules on a Playmate centerfold shoot is to make sure 'the presence of a man' is suggested in the photograph - a pipe, a shirt, a second wine glass.

The brand's relationship with women is an uncomfortable blend of liberation and objectification. Now, with the puppy parties and the pink bedrooms, a creepy infantilization has been added to the mix.

But Hef is no stranger to irony. Before he started Playboy in 1953, with a loan from his mother, he was the circulation manager of Children's Activities magazine. He's the world's most famous purveyor of sex but he masturbated for the first time at 19 and lost his virginity at 22. He was from a conservative home and escaped into the movies of the '30s and '40s. He sees himself as a romantic as a result. He owns the grave site next to Marilyn Monroe's.

Happy Ending?

Madison is now seeing magician Criss Angel and Wilkinson is engaged to footballer Hank Basset after a courtship shorter than the average Playboy Mansion party. Lately, at the mansion, 'there are some random-ass hoes walking around,' Wilkinson said to talk-show host Chelsea Handler after admitting she had been having Skype sex with Basset from her room in the mansion.

Two of the 'random-ass hoes' Wilkinson so charmingly (as always) refers to are 19-year-old twins Karissa and Kristina Shannon. They are reported to have become Hef's newest girlfriends. (Don't laugh: in the '90s he had Brandy, Sandy and Mandy.) 'I'm definitely not going to live alone,' the Associated Press reported him as saying.

How long will the new girls stick around? Who knows? Maybe long enough to launch their careers. Or to make sure they're in the movie. As the Playboy kingdom fizzles out along with Hugh Hefner's ability to get an erection without chemical assistance, there is talk of a biopic starring Robert Downey Jr, which could cement Hef's story as history. The book will then be closed on the Playboy era.