Neil Strauss Interviews Hugh Hefner for Rolling Stone - Rolling Stone
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Checking in With Hugh Hefner

At 72, the Playboy’s playboy’s got Viagra in his veins, twins in his bed and a new will to get up, put on his bathrobe and go to work

Hugh Hefner

Hugh Hefner at his Playboy Mansion, Holmby Hills, CA, February 17th, 1999.

Paul Harris/Getty

Somebody stop Hugh Hefner. He’s throwing parties again, hopping from club to club, getting his picture taken with Cameron Diaz and Dave Grohl one night and Jack Nicholson and Perry Farrell the next. He’s popping Viagra and dating identical twins, plus a third busty blonde. They are in their twenties and are very understanding when he wants to bring additional women into the mix. He is 72 years old.

After almost ten years of family life and supposed monogamy, Hef, as he likes to be called, is back on message and living The Life. To some red-blooded bachelors, the Playboy progenitor is the ultimate object of envy. “I want to be him,” says Vince Neil, the Mötley Crüe singer who’s “eternally engaged” to a Playmate. To others, he’s a visionary workaholic and a lucky womanizer. And to some, he’s just an old man still chasing tail.

In the forty-five years since he started Playboy and made his mark on modern history with the simple suggestion that nice girls have sex, too, Hef has become an artwork of his own creation — a living playboy, an icon as durable as the bunny logo itself. He furnished his universe with the trappings he’d always coveted — the silk robes, the round bed, the grotto of hot tubs, and the endless supply of celebrities and girls — and cast himself in the leading role of a fantasy based on movies he’d seen as a child.

His set is the Playboy mansion in Los Angeles — an invitation-only adult Romper Room, where we find Hef sitting in the library in his second skin of a red smoking jacket and black silk pajamas. On the table in front of him are the accessories that replaced his pipe after his 1985 stroke: a bottle of Diet Pepsi and a plate of cookies.Surrounded by pictures of his ex-wife Playmate Kimberley Conrad, Hef is full of energy, his left hand constantly stroking his chin while his right drums on the cookie plate.

Of course, this isn’t Hef’s first rebound. There was his joyful leap into bachelordom after the breakup of his first marriage, to Millie Gunn; the festivities that followed the end of his relationship with Barbi Benton, in 1976; and then, in true Playboy fashion, getting back in the game after his stroke. The difference this time is that he is older and everyone else is a half-century younger. Hef is a living museum piece that loves being on display. And you can touch it. There are no alarms, especially if you are blond and well-endowed.

Did you have any idea that you’d get so much attention just for going out partying?
No, no. I think that’s one of the reasons that I am doing the club scene more — particularly after having been off the scene completely by being married for the better part of a decade. I was not prepared for the reaction. A separation is always traumatic, so to come out of that tunnel and find that a whole new generation is waiting for me to come out and play is very nice. A lot of the new celebrities feel they’ve missed the party — missed the swinging time. And that’s the way I felt when I was growing up in the Depression, looking back at those images from the Roaring Twenties.

I also think the response [to his return] has to do with the time frame: Six years ago, it would not have been the same. Whatever was going on during the Reagan and Bush eras has changed. Now, as Prince suggested some time ago, it’s 1999 — it’s party time.

How did you meet your girlfriends, Brande, Sandy and Randy… . . .
. . . I’m Randy.

Sorry, I meant Mandy.
When I was clubbing. I met Brande [Roderick] at the Opium Den, a club that she had not frequented very often. And in May, about a month later, I met the twins — Sandy and Mandy Bentley — at the Garden of Eden.

What made them stand out?
They’re very special ladies, very special ladies. With the twins, they are actually college kids — nice Catholic girls from Chicago, my hometown. The night I met them, I said, “You girls dropped from heaven.” Then they had a drink with me. I got their first names but not their last names or phone numbers, and suddenly they were gone. It took me a month to find them.

Where did they turn up?
In school. One of them is in a premed program in Las Vegas; the other was in a private Catholic school in Chicago. coaxed them each into coming out here, and now they’re here almost every weekend.

How did you coax them? Love letters? Boxes of candy?
No, just talking to them on the phone. It’s a very special relationship. Mandy has just moved here, and Sandy’s coming out as soon as her semester is over.

Have you ever had a relationship with several people before?
Oh, yeah, sure. Not quite in the same way, though.

How is this different?
Well, we do everything together. Does it make it complicated when, on top of all that, you have your ex-wife [Conrad] living in a house next door? I suppose from the outside it looks like it ought to be complicated, but it isn’t. Over the years a number of my former girlfriends have remained close friends. I think that is a reflection of the kind of person I am — the way I treat people. So what could otherwise be a difficult situation is not. It’s very harmonious. There was more drama in my marriage than there is now that I’m dating three girls. And it’s been about eight months now.

Would you feel jealous if Kimberley started dating?
I probably would, I probably would. She does some dating. I still care about her, and vice versa. We still love each other.

How would you feel if Kimberley started dating twin brothers?
We’ll cross that bridge when we get there. But, actually, I think the fact that I am seeing three ladies rather than one probably does make it easier for her. If I were seeing only one person continually, then it would be a much closer comparison to the marriage, and that would be, by its nature, more difficult.

Would any of this be possible without the help of Viagra?
It would be very difficult without Viagra. I think they’re actually underselling Viagra, because it’s more than an impotence drug: It’s a recreational drug. It eliminates the boundaries between expectation and reality, and permits a level of pleasure that is otherwise just something you hope for. I think it’s as important, in its own way, as the birth control pill. It’s being tested now on women, because there’s some indication that it may have similar effects for them.

I know some women who take Viagra just to go out and party.
Well, we’ve done that. We’ve had some, you know, Viagra nights.

What are your thoughts on male desire? You’ve slept with more than 1,000 women, but when you see a beautiful girl, you still want her. When is enough enough?
They talk about Darwinian imperative — the idea that men want to pass their DNA on to the next generation. I guess that’s part of it, because you see it in nature with other species. Men have a roving eye. I think that in my own life it comes and goes, depending on what kind of relationship I’m in. In other words, while I was married, I was faithful to the marriage. I didn’t have any problem with that at all, after having lived the life I had lived before. Immediately after the marriage, I was seeing a great many women.

So do you still want to have more kids to pass your DNA on to?
I don’t think so. I’ve had two families, and that’s enough — unless I found myself in a relationship where that became very important to the woman.

I’ve heard that every night of the week, there’s a different theme at the mansion.
It’s fairly routine. Monday night is male night. I spend it with guys I’ve known for many years — my brother, Bob Culp and a few other friends. We have dinner and then pick an old movie — usually the kind of films we enjoyed when we were kids. And then later on that night, we go out with some friends to one of the restaurants. Tuesday night is family night, so the children and Kimberley are over here. Wednesday night is card night — gin rummy, and sometimes clubbing after. And Thursday is really the beginning of the long weekend. We usually go for dinner at the Atlantic and then to some club afterward. On the weekends, Friday, Saturday and Sunday are movie nights with friends. Friday nights are classic films, and Sunday nights are the new films. Usually Friday nights are better than Sundays. The early films are the stuff that dreams are made of.

How big of an influence did those movies have on you as a child?
A lot of my motivation came from the fact that I was raised in a home in which there was no display of affection. So my dreams, my definition of love, came from images that I saw in the movies or heard in the music of that time. I think my entire life has really been a kind of quest for the world that you found in songs — a quest for a perfect kind of love. And I think that love, for me, has always been defined, by and large, as romantic love the way it was in the movies. My dreams came from Hollywood. And I think that the world’s dreams — certainly the American dream that most of the rest of the world identifies with — come from the movies, too.

Who are the people in your inner circle?
Well, a lot of them are people you wouldn’t necessarily know. Bill Cosby, of course. And I’m seeing a lot of friends from days past again — Jack Nicholson. Then there are a lot of people that I didn’t know before who are coming to the parties, like Leonardo DiCaprio and Cameron Diaz. You name’em.

You’re socializing with a lot of young musicians now, like Courtney Love and Dave Grohl. Have your musical tastes changed along with your guest list?
The music that I care about is rooted in my youth. So I care more about jazz and the various permutations of jazz, although Brande went to see the Stones last night. There was a point in time, in the early Seventies, when the Rolling Stones were on tour and stayed with me for the better part of a week in Chicago, at the mansion. And Mick was here about a year ago.

How do you feel when you go to newsstands now and see Playboy surrounded by much more explicit sex magazines?
Over the years, particularly in the Seventies and Eighties, that was a major problem for us. The popularity of imitators like Penthouse and Hustler confused the very nature of what we were trying to do. So we became, in many minds, the high end of a genre of skin magazines. All that has changed, Now Penthouse and Hustler and the rest are becoming hard-core, and the men’s field of magazines is all doing variations on Playboy. Everything from Maxim to GQ to Details to Esquire are doing Playboy. I just received the new Sports Illustrated, and the bathing suits are getting skimpier and skimpier — almost disappearing.

Are career opportunities for centerfolds different now than they used to be?
Yes, dramatically, I think the taboos have disappeared. It’s taken a long time. It really began with Marilyn Monroe. Not because of her nude calendar photos, but because of the way she responded to it, saying, “I had nothing on except the radio.” That attitude and the way the public responded to it, during a very repressive time in the Fifties, was the beginning of the legitimate connection between celebrity and nudity. Now, any time I go out, there’s a continual flow of women coming up to me who want to be Playmates. And, of course, you’ve got Pamela Anderson with that video out, and all the controversy surrounding Clinton and his sex life. I mean, the only people that are hysterical and upset about it are the congressmen.

I know you’re not a fan of his, but what do you think of what Larry Flynt’s been doing by exposing the Republicans’ hypocrisy?
Well, you know that Flynt is not exactly one of the guys that I admire. But I think that what he has done was a very smart promotional notion. And it does reflect the hypocrisy of it all.

You always find hypocrisy in government. That’s the nature of the game, because there’s hypocrisy in our American attitude toward sex. It’s the conflict between Puritanism and the shame and guilt related to sex, on one hand, and the fact that we love sex. That kind of hypocrisy used to live in the shadows, but when Jay Leno starts making explicit jokes about sexuality, it is very difficult to put the genie back in the bottle.

How many of our ambitions do you think are motivated by sexual drive?
How many people have said that they got into music because they wanted to meet girls? One of the things that is fascinating to me is that with all the taboos and controversy surrounding sex, the reality is that sex is probably the major motivating factor on this planet.

What do you think has become of the sexual revolution you helped start?
There was a point in the early Eighties when they were announcing the end of that revolution. And then of course, the arrival of AIDS and the politicization of the disease. On many levels now, it’s like coming out of the tunnel.

What would you do if your photo editor came up to you and said he had just found out that the woman you were planning to shoot as your next centerfold was HIV-positive?
I don’t know. Rebecca Armstrong was a centerfold and is HIV-positive — and may have been at the time she was a centerfold. I’m not sure. She thinks she acquired it in her teens. But I don’t I know about that question. I’m not sure.

What about plastic surgery? Do you think it’s gone too far?
I think it’s like medicine, Anything that makes you feel better about yourself is perfectly appropriate. Why should one be required to stay in a box that was handed to them by either nature or by their parents or peers? Why not create yourself? Why not be the person you want to be? What about you?

Have you reinvented yourself again?
To some extent. But what I am doing is revisiting the guy I was before. And with a vengeance.


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