Hugh Hefner – Portrait of a Young Man

Hugh Hefner
Hugh Hefner, enjoying his third bachelorhood in 2005, alongside girlfriends Holly (second left), Bridget (second right), and Kendra (right).

I was lucky enough to visit the Playboy Mansion about half a dozen times, thanks largely to friendly Playboy PR man Bill Farley who has since retired and written a book. In addition to a handful of generic promotional events (a Johnnie Walker cigar evening here, a pro-marijuana fundraiser there), Bill invited me to some Playboy-centric affairs, such as their annual Playmate of the Year or Playboy Jazz Festival announcements. These were more civil gatherings, perhaps because the guests were more Hef’s vintage. I saw Milton Berle one time, Don Adams another. Gene Simmons seemed to be a constant presence.

My first visit, in 1994, was the best, a one-on-one with Hef for about an hour. It began in a downstairs anteroom where a naked portrait of his second wife was displayed. Then we moved out to the patio, surveyed by flamingos and peacocks. Hef sported purple pajamas and red dressing gown, and drank a lot of Diet Pepsi. This was during his domestic period when a “children at play” sign warned drivers to take it slowly as they rolled up the drive to the mansion. He had married former Playmate Kimberley Conrad in 1989 and they were raising two young sons, Marston, who was four at the time, and Cooper, who was almost three. The couple split in 1998 (she moved next door and they stayed married until 2010), and Hef resumed his man-about-town ways, parading with a gaggle of oddly unattractive bimbos who couldn’t hold a candle to the 8- and 9-level “girls next door” who seemed to grow on trees in Los Angeles. Each to their own, I guess.

Hef was a chipper 68 when we spoke. My questions were evidently amazing and Hef laughed a lot. Bill the PR man said he learned a whole lot of new stuff about his boss by listening in on our chat. And Hef, a fellow journalist of sorts, delivered the ultimate parting compliment, “Good interview!” Here are some highlights.

I wonder if you could describe your typical day?

It’s certainly very different than it was a few years ago. It begins at around 10 – I have my own office staff here. The far wing of the house is all office. And I deal with a variety of business things, most of them editorial, because I’m not much involved anymore in the day-by-day – and haven’t been for a long time – business part of the company. The business part of the business hasn’t really lit my fire. But I deal with editorial decisions, marketing things, creative things, and just a variety of kinds of questions and concerns related to interviews and things of that kind. And then by late morning or early afternoon I’m upstairs either in my attic office area working on the autobiography, or in our scrapbook room. The scrapbooks are the autobiographical source material and I’m getting them up to date.

You keep pretty voluminous records?

Very voluminous, from very, very early on. It’s very interesting in looking back in retrospect and seeing how – and it’s probably true for everybody, but it’s really clear in my life – how I was in rehearsal for the life that I have lived as an adult from a very early childhood. I produced a penny newspaper when I was about nine years old. I produced a school paper in the seventh grade that lasted for many years. I created a tremendous number of comic books, and short stories that were mystery and horror and science-fiction and fantasy, that were not simply stories but also were illustrated and bound as books. I started a club in the summer of 1941, I think, called the Shudder Club for my friends in the neighborhood who were fans of mystery stories and horror movies and that kind of thing, and produced that summer about six issues of a magazine/book, monthly, that was devoted to that subject.

You’ve said your parents were repressed, but obviously they must have encouraged your creativity?

What was missing in my childhood – and it damaged my brother more than it did me – was an all too-American inability to show affection or love. Although we felt secure in our home, knew that we were loved, there was never any demonstration of any kind of affection between my parents or between my parents and ourselves. Beyond that it was a very idealistic and very supportive environment. I had a really quite a wonderful childhood. But I think that in a very real way I escaped with that void in the emotional connections of our home. It’s clear to me now that I escaped into the fantasies reflected in many forms in my childhood and into my own dreams and fantasies, much of it inspired by the movies and the music of that period which tended to be romantic. I think that in a very real way, love of any kind for me became the equivalent of romantic love as it is expressed in those forms. One of the things that’s fascinating to me is that much of my life has been a quest for that impossible dream, that dream of ideal romantic love. And the obsessive side of my life, I think, was very much a part of that – a series of sexual adventures, et cetera. The remarkable thing now is that I have managed to come full circle and find in a marriage and imbue in a marriage a romanticism – to make a marriage itself and the presence of children a romantic ideal, something that was inconceivable to me a few years ago.

Have you ever been tempted or strayed since you got married?

No, no. I have too much at stake here, I have too much of a perception of who I am. If I were fucking around on her, I would be fucking around with myself.

Did you sign a prenuptial?

We have a prenuptial, sure. But that’s only because I have other children, responsibilities.

The first person you made love to was your (first) wife?

Yes. Right before we got married. She waited until she was graduated so she didn’t have to worry about being pregnant. She was from a lower middle-class, blue-collar family. No one in her family had ever gone to college. She wanted to be sure she graduated.

I thought you’d already reinvented yourself by then as Hef, as the rogue man-about-town?

I think that’s part of that dream fantasy, and I also think that there was a parallel there. I did the same thing in high school, but I didn’t realize that’s what it was all about. When I was 16 years old I had a mad crush on a girl that I met that summer. She taught me the jitterbug and she seemed like the ideal “Betty Co-ed.” Her name was Betty. And she preferred another friend of mine. My response to that was to completely reinvent myself. It was then that I started referring to myself as “Hef” instead of “Hugh,” changed my wardrobe, started wearing saddle shoes and cords, started writing a column for the school paper called “Platter Patter” which was a review of records, and signed it “Hep Hef.” That is, in a very adolescent, simplistic way, exactly what I did after I started the magazine and when my divorce became final and I kind of stepped out from behind the desk and became Mr. Playboy. With the same kind of props, a pipe, the smoking jacket, the 300SL. It was just like an adult, upscale version of the thing I did when I was a kid.

Hugh Hefner, announcing the lineup of the Playboy Jazz Festival, at the Hollywood Bowl, in 2001. Young Hef watches from above.

Are you the last of the great playboys?

No. These things come and go. Somebody once said and I think they were closer to the truth, I think it was the New Republic in the middle ‘80s, he said, “After all is said and done it may turn out that Hugh Hefner was the last great romantic.” And I do think that my life has been a kind of a romantic odyssey.

In what way has your attitude to women changed over the years?

I do think that I did some conscious raising along the way. I’ve always been a guy who had lots of female friends and was able to see the inequalities in power relationships, and have always felt connected to the underdog whether it was in a sexual situation or political or anything else. That’s the kind of person I am. So I was the kid in school who the girls would come to. There was a character on radio back then called Mr. Anthony, who gave advice. And I was the Mr. Anthony of my school. I was the one the kids could come to if they had their problems.

Was it a drag, though, to be the girls’ friend rather than a potential lover?

Oh well. It took me a while. I was in rehearsal for a long time. I did make up for it.

Did you ever worry that you were being used by women?

We’ll never know, will we? I’d like to tell you that I spent a lot of sleepless nights worrying about that! . . . I think the major sex object created by Playboy was probably me. I have been exploited. I’ve managed to rise above it and haven’t really minded it that much. But at the same time, you’re absolutely right. Have there been instances where I could see clearly that it was a manipulation, et cetera? Sure. And did I back away from it? Absolutely. I’ve seen myself in situations where women would come on to me and their motivations were very transparent, and that’s a turn-off for me.

Do you have any vices or excesses these days, apart from copious amounts of Diet Pepsi?

No. It’s a pretty mellow life.

Were you ever much into cocaine?

No, no. As a matter of fact I hated cocaine. I hated it because of the impact that I saw that it had on people’s personalities and the lives that I saw ruined by it, people close to me. Tony Curtis, it practically pushed him off the edge and I helped him beat it, and he talked about it in his book and elsewhere. I helped to bring him back. Cocaine is a crutch for people who need that boost. The only recreational drugs that ever had any meaning for me at all are those that enhance lovemaking. Cocaine takes you in some other kind of place. I had never at the time of the drug scandal, with Bobbie Arnstein (a trusted associate who committed suicide in 1975 after being convicted in a federal drugs probe aimed at Playboy), I’d never even seen anyone using cocaine. In my particular circle of friends I was probably one of the most conservative where drugs were concerned. I don’t think I smoked grass for the first time until the late ’60s. I missed the whole psychedelic, LSD thing that many of my friends were into. It was in the ’70s that I really tried recreational drugs, but coke was not among them.

You’re pretty reclusive. You don’t really leave the estate that often, do you?

No. I have no occasion to and have no motivation to.

What happens if they want to go to the zoo?

Oh, we’ve gone to the zoo. We went to the San Diego Zoo.

But you wouldn’t go out for a Sunday drive?

I have, but not too often. That’s the kind of thing my Dad used to like to do, and I used to get carsick. I wanted to stay at home. Those were the things you did on Sunday, instead of playing, instead of hanging out with your chums. I had a very rich imagination when I was young. It was the fertile ground that everything else grew out of.

What advice would you give to young, would-be media moguls?

My advice to everybody, whether they want to start a magazine or anything else, is follow your own dreams, hold onto your dreams. I think that too often there are too many things in society that supply justification for selling out or taking the safe way. And if you don’t try and if you don’t really do what’s in your heart — whether it’s in a personal way or in your business or anything else, you’ll regret it for the rest of your life and you’ll never know. I’m enjoying these years the most of all because I’m savoring the awareness of all these wonderful adventures and recognizing that I’ve made some difference in the world in which I live and done it with great style and pleasure. And now I’m in a very safe harbor, in a wonderful relationship, a wonderful marriage, two fantastic kids. When I say follow your dreams, following your dreams may take you to a farm in Indiana. Do what you want to do. The real message is life is over in a minute and a half. It’s the only chance you’re gonna get, it’s the only life you’ve got. Don’t follow the herd and do what everybody else thinks you should do. Do what you really want to do with your own life, and take a little time to figure what that is.

NOTE: Unrelated to the above interview, my gossipy rock bio Strange Days: The Adventures of a Grumpy Rock ‘n’ Roll Journalist in Los Angeles is available here. For more info, go to

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Dean Goodman