The Playboy Founder’s Final Interview


A representative for Playboy confirmed on Wednesday that Hugh Hefner had peacefully passed away at age 91 on Wednesday from natural causes at his home, The Playboy Mansion. Below is his final ever interview with PEOPLE. 

On March 17, 2016, Hugh Hefner was having a ball. In advance of his upcoming milestone birthday, the Playboy founder was at home, paging through his painstakingly maintained scrapbooks and reams of personal photos, testimonials of a career and life that spanned nine decades.

Wearing his signature red silk robe and black smoking slippers, Hefner chuckled as he recalled the lighter moments and smiled fondly as he reminisced over the lovingly preserved pages, like those that featured cartoons he sketched as a child.

There, in an upstairs office of the storied Playboy Mansion, during what would be Hefner’s final interview, the civil rights activist, philanthropist and oft-controversial publishing pioneer shared his treasured memories with PEOPLE’s Aili Nahas — as well as revealing to her the legacy he hoped he’d leave behind.

You grew up in Chicago. What was that like?

“It was a very happy childhood for my brother [Keith] and myself. We were very close. We were similar but I was two and a half years older so he tended to imitate and look up to me. We had similar interests. We both liked girls! I started drawing at a young age. My family, my mother, in particular, had photo albums from her school days. I don’t know if that’s where the inspiration [for the scrapbooks] came from. I was writing and cartooning and writing short stories from grade school on. I still have all of [the comic books].

At 27, you were working to start Playboy Magazine and you were married [to Millie Williams] with a young daughter. What was that time in your life like?

It was an exciting time because I had no idea how things would turn out. I launched the magazine on $5000 dollars. My mother loaned me $1000. The first issue came out at the end of 1953. I knew I needed something original. I had a photographer shoot a 3D feature for the first issue and learned it would cost too much money. When the 3D thing turned out to be too expensive, at that same moment I came across the photos of Marilyn Monroe. People had heard about it but they hadn’t seen it. And that was the first issue. 

Playboy’s original name was Stag Party. Why did it change?

I got this letter from a New York law firm who represented Stag Magazine. They considered the name Stag Party an infringement on their title. If we used the name they would have threatened legal action. The magazine was going to press [the next week] and we didn’t have a title. So we decided on the title. The word Playboy [wasn’t] used very much anymore. It [made] you think of the 20s. I wanted an animal symbol. When it was Stag Party it was a stag and then it morphed into a rabbit. The bow tie made it elegant.

What motivated you in the early years?

I was always a dreamer and I worked to make the dream come true.

What kind of father were you in the early years with your older two children [Christie, 64 and David, 61]?

I was an absent dad. Once the magazine started, I really had two families. The dream was the magazine. I worked through the night all the time.

You discovered and popularized so many artists and writers like Shel Silverstein, Alex Haley, Ray Bradbury and Lenny Bruce, and in 1955 you published a highly controversial story, The Crooked Man, which told of a dystopian future in which homosexuality was the status quo; it’s now championed as an important part of the early gay rights movement.

Esquire had turned [the story] down because of its controversial nature and I said this is exactly what we’re looking for. It got people talking. For Playboy to start off the ground from zero, you don’t start a major company or magazine like this unless there is some kind of magic going on. And there was magic going on.

In 1960, you opened your first Playboy Club. Eventually, you discovered issues of racism at some of these clubs.

There were two syndicated Playboy clubs. The first one we ran, but while we were busy working on other ones, there were syndicated clubs in New Orleans and Miami and in both cases, there were segregation problems. We said to the guys, you have to accept the members, racial consideration is of no importance. You have to accept them if they’re members. And we literally bought back the franchises and ran them ourselves. 

Over the years, you also fought for a lot of social issues: abortion rights, birth control… were you ever afraid you were going too far for the time?

Part of the concept behind the magazine was breaking barriers. And it wasn’t just a sexual thing. It was racial and doing the things that were right. And in the process that set Playboy apart. 

When did you start wearing the silk pajamas and the robe?

It was very early [at the Chicago Mansion]. It was comfortable and then I knew I was getting away with something. It was good for the image and good for a lazy guy. It became a uniform. I probably own 50.

Ron Galella/WireImage

You bought the Playboy Mansion in 1971 — did you build the famous grotto?

Yes. By the time I walked the property, I knew pretty much what I was going to do. The backyard was flat and it had nothing special going on. It didn’t have a tennis court and it didn’t have a swimming pool. But because of that, I was able to do something special.  I had a miniature version of the grotto in Chicago in the indoor pool in Chicago. Behind a waterfall was a little cave. The pool parties started in Chicago. I don’t swim! I wade. 

In 1985, you had a stroke and you called it a stroke of luck. Why?

Because I survived it and I got a lesson from it. I started taking better care of myself. I stopped smoking. I thought it was a second chance. 

You married Kimberly Conrad at the age of 63. Did your second time being a husband and dad [to Marston, 27 and Cooper, 26] feel different?

Yes. I was more into the marriage the second time. It was good. I was ready to be a dad again…having two boys was a parallel of my own childhood, my brother and I. 

After your marriage ended, you were a bachelor again and became famous for your nights out with your seven girlfriends- what was that like?

It was pretty nice. I reinvented myself.

Your reality show with Holly Madison, Kendra Wilkinson and Bridget Marquardt premiered in 2005 and became an instant hit- what was that era like?

It was a happy time. I thought it was good timing.

In 2013, you married Crystal Harris — why did you decide to get married again?

I didn’t give it a lot of thought. I wasn’t really planning on getting married. She indicated that she wanted. And I don’t think either one of us has ever regretted it. We’re very happy together. I’m not sure how, but something clicked there very quickly. Crystal is one in a million. I feel very lucky to have her in my life in this way. 

After all these years, why do you think Playboy is still relevant?

I think it’s a fantasy life for a lot of people, including me. And it’s been real and relatable all through these years. Because it is real. 

What is getting older like for you?

It’s nice to look back on very sweet moments. I just think I’m very very blessed.



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