Hugh Hefner- Mr. Playboy

by David Pulizzi
(originally published June 2008)

Admiring and envious men the world over know Hugh Hefner as the founder and public face of Playboy, the men’s magazine with the saucy centerfold that first hit American newsstands in 1953. What most men — and women, for that matter — may not know is that Hefner has been a serious jazz fan since he was a teenager growing up on the West Side of Chicago in the late ’30s and early ’40s. Like his boyhood pals, he was partial to the popular music of the era, swing, but he also fancied Dixieland. Hefner has never lost his taste for the ebullient sound of early jazz. In many ways, the music of Bix Beiderbecke, the Dorsey Brothers, Harry James, Artie Shaw, and their contemporaries has provided Hefner with the perfect soundtrack to his life.

To celebrate the fifth anniversary of Playboy in 1959, Hefner conceptualized and then hosted a jazz festival for the ages — an affair that Billboard magazine trumpeted as “the whoppingest jazz festival in history.” During that three-day weekend in early August, nearly every major jazz artist of the day performed within the cavernous confines of Chicago Stadium.

Though the festival was both a critical and popular success, Hefner didn’t stage a follow-up until 1979, this time to celebrate 25 years of Playboy. Held at the Hollywood Bowl in Los Angeles, the lineup of talent was at least equal to the lineup that shook Chicago Stadium 20 years earlier. As the ’79 festival wound to a close, Hefner took to the stage to announce that henceforth the Playboy Jazz Festival would be an annual event.

This year, during two days in mid-June, the Playboy Jazz Festival will celebrate its 30th anniversary at the Hollywood Bowl. In March, a month before his 82nd birthday, I spoke to Hefner about the milestone and about jazz in general. During our conversation, I discovered that, as his reputation suggests, the founder of Playboy is personable, gracious, good-humored, and intelligent. In Hugh Hefner, I thought, shortly after hanging up the phone, jazz has a fine and able champion.

JAZZIZ: First of all, congratulations on 30 years at the Hollywood Bowl.

Hugh Hefner: Well, thank you. Hey, time flies when you’re having fun. It’s amazing.

The Playboy Jazz Festival is now considered a major annual event in the jazz world. Obviously it’s two days worth of fine entertainment, and you yourself have often referred to it as a “wonderful party.” But beyond that, do you feel that the festivals have made an important contribution to jazz?

I think it’s kept the music alive. I mean, people have been prematurely reporting the death of jazz since the arrival of rock and roll. Jazz is the music that I grew up with, the music of my youth, the music that fueled my dreams. So when we were celebrating our fifth anniversary at the end of the 1950s, we held the first Playboy Jazz Festival. That turned out to be really an iconic gathering of musicians that would never be together again.

The Modern Jazz Quartet, 1983

Why did you choose to celebrate the fifth anniversary of the publication with a jazz festival?

Well, again, I think it’s because the music had such special meaning for me. And we covered jazz from the very beginning. We had a piece on the Dorsey Brothers in the very first issue. I just felt that it was part of the party. In other words, if you are dedicating a magazine to lifestyle and leisure activity, you can’t do it without the music. And the coolest kind of sounds, certainly back in those days, was jazz. As a matter of fact, it wasn’t till the latter part of the ’60s that we started encompassing other kinds of music.

Was that decision dictated by popular taste or had your own tastes expanded?

It had more to do with my editorial sensibilities — the recognition that the music tastes of our audience had grown to such a degree. Whole generations had grown up that hadn’t grown up on the music I had grown up on, and I had to recognize that fact. My own tastes have never changed a great deal. I play Bix Beiderbecke here at the house most of the time. That’s the background music at the Playboy Mansion.

Do you spend a lot of time just listening to music?

Well, I spend a lot of time in an environment where music is a part of it, yes. In other words, we entertain with regularity, and whenever there is anybody in the house, there’s music playing.

Will you be attending the festival this year?


Have you ever missed a festival?

I think I’ve been there every time. I’m not there both days, but I am there on the opening day, and I don’t think I’ve missed one.

You were born in 1926, and you grew up on the West Side of Chicago. Swing bands were popular as you were growing up. When did they start making an impression on you?

Well, music made an impression on me from very early on. I was also a huge fan of movies. That’s where I escaped into the dreams. And I loved the musicals. And, of course, radio was hugely popular during that time. You would get the big-band remotes from all over the country. So I was a big fan of the big bands by the latter 1930s, when I was in seventh and eighth grade. I learned to dance in eighth grade, and I had my favorites early on — Artie Shaw, then Glenn Miller, and then Harry James.

I assume your friends listened to that music, as well.

That was what was unique and what was wonderful about that period — the universality of really good popular music. And it was all, by and large, jazz oriented. It was wonderful. And I had a big taste for Dixieland.

Do you still listen to the Big Bands?

Oh, yes. And I pay attention to a British singer named Al Bowlly, who was kind of the British Bing Crosby in the early 1930s. I play a lot of his music, too.

A minute ago you said something that reminded me of something I wanted to bring up to you. In a 2003 interview with James Liska, you said, “Being raised in a very typically Midwestern Methodist home with lots of repression, music itself was a great source of dreams and fantasies for me. I think music and the movies were the major influences and the major kind of escape for me into the other possibilities of what being alive might be. I think my life has been a quest for a world where the words to the songs are true.” I’m wondering, as you look back at your life, do you see it as the fulfillment of that quest? Have you made the words to the songs your reality?

Oh, yes. And I’m still living a boy’s dream. Absolutely.

Evlis Costello

A boy’s dream?

Yes. And my connection to the boy who dreamed the dreams is what my life is all about. You will find in my home, particularly in the bedroom, a lot of artifacts and memorabilia from childhood. From posters of Flash Gordon and rocket guns and The Maltese Falcon to busts of Frankenstein’s monster and all manner of other kinds of things of that sort. I think it’s that connection with childhood that keeps this all so delicious. People who see my life from the outside — depending on their own particular dreams and fantasies — think my life seems rather special. But I can’t begin to express that what they see is only the beginning of it, that it is so much more than that. It’s not simply because I’ve accomplished so many of the things that I wanted to accomplish; it’s living the life and enjoying the friendships that have become a part of it. I have an ongoing family of friends that I have shared much of my life with, and those friendships and that love is what makes it all worthwhile.

Have you ever felt that there is anything that your life is missing — anything that you might have wanted to do that you might not do?

No. There are most certainly decisions in one’s life that one might have done differently in business and on a personal level. But those are all roads untraveled, and, quite frankly, I think that’s a very dangerous game. It’s the old Ray Bradbury “butterfly effect” — you change one thing, and you don’t know where it leads.

You’re going to go to your grave a content man, aren’t you?

That’s my thinking, yes.

Let me get back to the jazz festival. Leonard Feather called that first festival in ’59 one of the greatest weekends in the history of jazz.

He called it the single greatest weekend in the history of jazz.

There you go. Still, though, you didn’t stage another jazz festival for 20 years, in 1979. Why did you wait so long?

As a matter of fact, I had actually thought about doing it a second time. Then I thought, how are we going to top ourselves? Also, the jazz festival was in August of ’59. In October of ’59 I started recording “Playboy’s Penthouse.” It didn’t start airing until January, but we started actually taping the shows in October. In December, I bought the first Playboy Mansion in Chicago, and in February of 1960 we opened the first Playboy Club. So in the space of less than six months, my life changed dramatically. I became, in fact, Mr. Playboy. I started living the life of the fantasies that were expressed in the pages of the magazine.

At the Playboy Clubs and on “Playboy’s Penthouse” and later, on “Playboy After Dark,” you showcased a wealth of jazz talent.


Did the demise of those clubs and the television shows have anything to do with your decision to re-launch the festival?

The decision to re-launch the festival was the fact that we got to our 25th anniversary. And what were we going to do to celebrate the 25th anniversary? I was living out here in L.A. In addition to a number of other things that we also did in that time frame, the most logical thing for me to do was another jazz festival. And the notion of doing it in the Hollywood Bowl brought together for me my two loves: jazz and movies. Because I had seen the Hollywood Bowl in a whole host of movies when I was growing up. So putting jazz in the Hollywood Bowl was, again, a boyhood dream. The intention, of course, was to do it just as a single event, just as we had done for the fifth anniversary. But it proved so popular, we decided to do it a second year, and here we are 30 years later.

When you show up at the Hollywood Bowl for these festivals each year, does that rekindle your sense of childhood dreaming and wonder?

Oh, yes. You can’t share that music in the Bowl setting and not get some of that childhood kick.

Playboy Jazz Festival at The Holywood Bowl

You’ve singled out big-band music as your favorite type of jazz. How did you feel when bebop came along?

I liked it, but it was not my music.

How about some of the “out” stuff that came along later?

Well, I think that what you like has a lot to do with when you begin dreaming the dreams. I think it has to do with childhood. But to some extent also, it must be said that I feel blessed to have grown up in a time in which the music was so romantic. I sometimes feel badly for young people growing up now, when the only music that they can say, in effect, is their song, you know, turns out to be impersonal rap.

I assume you have a love for beautiful melodies.

Yes. And lyrics. That’s one of the reasons that I loved musicals when I was a kid. I was a big fan of Alice Faye. There were moments that could break your heart that were expressed in a song.

Hugh Hefner Promo Shot 1957

You’re really just a romantic guy, aren’t you?

Oh, absolutely. And there’s something else that must be said. I was raised in a home without prejudice, and witnessed prejudice for the very first time when I went into the Army during World War II. And I saw anti-Semitism and racial bigotry. And it was something of special pride for me to break the color barrier with our television show “Playboy’s Penthouse,” and do the same with the Playboy Clubs. It was very controversial to put black performers into a social setting that appeared to be an apartment party, and have black and white guests and performers interacting.

I think the television show was banned in parts of the South.

We had no distribution in the South at all. And breaking those color barriers was very meaningful to me. And I then did the same thing with the clubs. Jazz was part of all that.

In recent years a lot of non-American acts have performed at the Playboy Jazz Festival. From Cuba, for instance, you’ve brought in Los Van Van, Chucho Valdés, and others. With that in mind, I’m wondering if you feel there is a sort of unspoken political component to jazz in general and your festival in particular.

Well, that’s in effect what I was really saying when I talked about the racial aspect of it, because I think that there is a political side to the entire racial question. And I do think, without question, jazz has been cited on a number of occasions as the one true original American art form. It is also the one American export in addition to movies that the rest of the world loves. The America that the rest of the world loves doesn’t come from Washington; it comes from Hollywood, from the movies and music that came from — and continue to come from — America.

Have you ever thought of yourself as an important advocate for racial integration in America?

Yes, I think so. In other words, I think that I’ve played a very real part in changing social sexual values; it’s obvious in terms of the sexual revolution. But I think that it goes a good deal beyond that, and it does involve race and pop culture. They are all intimately interconnected, and I’ve communicated the notion that having liberal views on race and life, et cetera, can be cool. It’s the way to be. It makes you a complete human being. Prejudice stunts you and makes you half a person.

In the Liska interview that I mentioned earlier, you said, “I look back at those images of the jazz age — F. Scott Fitzgerald, bootleg booze, flappers — and thought of it as a party I had missed.” Do you still associate jazz with a good, lively party?

Yes, I do. And the reason I do is because the jazz that I identify with is the less cerebral kind. It’s the kind that comes from the big bands, Dixieland, et cetera. The jazz festival at the Bowl has been referred to on a number of occasions, by me and others, as one great party. And I think that the party theme has always been what Playboy was all about. In other words, it’s a response to Puritan repression. It’s the other half of who we ought to be, the part that celebrates the very fact that we are alive.

You once quoted H.L. Mencken, something to the effect that a Puritan is someone who —

Someone who is unhappy because he knows that someone somewhere is having a good time.

Right. Okay, here’s a hypothetical for you. You’re banished to a desert island. You can take either your collection of jazz records or your collection of beautiful girlfriends. Which collection do you take?

I would take the girls. I’m a jazz lover, but the girls come first. Human relationships, you know. (laughs)

It’s really been a good life, hasn’t it?

Yes, it has been.

Are you a natural optimist?

Yes, I am.

And a dreamer, as well?

Yeah, very much.

So you’re a romantic, optimistic dreamer?

That’s who I am.

One last question: Do you read the magazine or do you just look at the pictures?

I do both.

So do I. Actually, I like the articles more than the pictures. I think I’m the only guy who’s ever said that for real.

It’s the combination of both.

Must be. Anyhow, congratulations again on a job well done for many years.

Thank you.

Hugh Hefner
Hugh Hefner

April 9, 1926-September 27, 2017








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