LOS ANGELES, CA - JANUARY 16:  Hugh Hefner poses at Playboy's 60th Anniversary special event on January 16, 2014 in Los Angeles, California.  (Photo by Charley Gallay/Getty Images for Playboy)
Hugh Hefner's most memorable TV moments
01:24 - Source: CNNMoney

Playboy publisher Hugh Hefner died at age 91 this week. CNN’s Breaking News Director Amanda Wills has a conversation with Town & Country Senior Digital Editor Lindsay Silberman about their summer working at Playboy nearly 10 years ago.

Amanda: I had only been in New York City for three days when I reported for work at Playboy nearly a decade ago. I was raised in an evangelical family in Tennessee, where the only talk about sex is that it was a sin outside of marriage. The walk, of course, was a whole lot different.

Playboy changed all that for me. My exposure to sex culture forced me outside my comfort zone. It was the first time I really thought about my place as a woman.

Lindsay: I romanticized what it would be like to work at Playboy as a woman. But I struggled with it—at least initially—more than I’d anticipated. I was in my early 20s and insecure. I hadn’t quite figured out who I was yet. Talking about sex was something I did with girlfriends. But the thought of having those conversations at work, with colleagues I barely knew? My worst nightmare. Or so I thought.

It turned out to be the most liberating, empowering experience of my young adult life. There’s a certain confidence to be gained in that kind of scenario. Being pushed out of your comfort zone. I expected to learn about writing, editing and how to lay out a magazine. I didn’t expect to come to terms with my own sexuality. It was an environment where female sexuality was normalized. And celebrated.

Amanda: I think people have very complicated feelings about Hugh Hefner. He was a progressive figure, a fighter for civil rights. Playboy’s first interview was with Miles Davis, and it was written by Alex Haley. And there’s no doubt that Playboy celebrated women. But did it do it in the right way?

Lindsay: I suppose that depends on your bias. In many ways he was a champion for women. He once said, “The whole 1950s notion was find the right girl, get married, move to the suburbs and then hang out with the guys while she stayed home with the babies. I felt that was sort of sad.”

I think he appreciated that women were powerful at a time when most men felt otherwise.

Amanda: But then again, the woman you see in Playboy is a deity. She isn’t real. She doesn’t spread her legs. Her vagina is carefully, artfully airbrushed. She is innocent, angelic. The words “slut” and “whore” aren’t part of the Playboy vernacular.

But just because women aren’t spreading their legs doesn’t mean they aren’t seen as objects.

Lindsay: Right. It would be naive to think that the subscribers all truly valued the “female empowerment” aspect of it. Let’s be honest — most of them were in it for the racy photos. There was so much more to the magazine than that, though.

Amanda: The magazine was made for men. We know this. And many of the famed bylines were men. That was the Playboy the public saw. The Playboy I saw was a masculine culture, sure, but it was also one where brilliant women were also driving the prose you read, the photos you saw, and the ads that paid for all of it.

It was the women behind the scenes, not on the pages, I wanted to emulate.

Lindsay: People always ask me if I felt objectified as a female intern there. I actually had the opposite experience. Didn’t you? Since the majority of the editors were men, they truly valued my perspective as a woman. They listened intently to everything I said, as if I was the keeper of all the female secrets. It made me feel important and respected; I definitely left with way more confidence than I had when I walked in.

Amanda: Yes. We were encouraged to explore what we wanted to do there — from the day we went through the archive rooms of the early issues just to learn, to the time I interviewed Dorothy Herzka, Roy Lichtenstein’s wife. No two days were the same, and every door was always open.

And at the center of all of that was Hef, who spoke to me on the phone in my first week.

Lindsay: I remember him calling the office constantly. His level of involvement was the most shocking part of working there. I had assumed he was just a figurehead who sat at the mansion in a silk robe smoking cigars. But he would scrutinize every single word of the magazine—every single comma—before it went to the printer. Even the captions!

Amanda: The magazine was him. Every page had his imprint. And that was why you had a magazine that wasn’t niche. It talked about race. About sex. About drugs. About politics. And it did it all before the digital age.