When I was a student at the University of Florida, studying film during the day and writing freelance stories at night, I landed two choice assignments. Choice, that is, for a horny, unrequited, socially awkward twenty-year-old.
First, I got to spend an afternoon hanging out with Russ Myers, a notorious film director and king of loopy seventies porn, the man who gave movie critic Roger Ebert his notorious film credit on Beneath the Valley of the Ultra-Vixens. That was a wild day.
The other unforgettable assignment was interviewing Playboy magazine photographer David Chan, who came to Gainesville to uncover the most delectable Gator coeds for “Girls of the Southeastern Conference” pictorial. Chan was a delightful guy with an enviable job. Hundreds of beautiful women were lined up outside his headquarters at the University Holiday Inn to bare their, uh, natural assets.
But Playboy and I go back about a decade or so earlier to the time when I discovered my dad’s prized stack of 1960s Playboy s in a cardboard box in the attic on top of an old cedar wardrobe. And by the time I was thirteen, I ordered a subscription of my own. And once a month ever since, I’ve looked forward to the arrival of the next issue.
A female friend jokingly asked if I read Playboy for the articles. Articles? I answered. Are there articles in Playboy ?
Apparently, there are because my guest today is Chris Napolitano, the magazine’s editorial director. If you look at the masthead, the only name listed higher is the magazine’s founder, Hugh Hefner.
Napolitano began his career with Playboy in 1988 as an editorial assistant in the fiction department and now, in his 20th year with the magazine, is responsible for the day-to-day editorial policy and operations of Playboy magazine. He reports to Hef and is based in the company’s New York publishing headquarters.
Chris Napolitano LinkedIn • 1-year Playboy subscription from Amazon.com
ANDELMAN: So, when did you guys start slipping articles in between the photos?
NAPOLITANO: When did that happen? Ever since the first issue in 1954. In fact, we started slipping more nude photographs in the book over the next ensuing years and decades. It was pretty article-heavy right from the very beginning.
ANDELMAN: That’s true. I do know that because I have read an awful lot of articles in there. I’m a huge fan of the Playboy interviews in particular, which are a wonderful part of the magazine, and I think there’s probably a lot of women out there who only read the magazine for things like the interview.
NAPOLITANO: It’s the one that gets attention. We have a great tradition going back more than 40 years with the Playboy interview.
ANDELMAN: How do you decide who’s appropriate for the interview?
NAPOLITANO: Well, the rule of thumb is household name. We usually don’t introduce personalities or thinkers no matter how interesting we might feel the things that they have to say are. They need to reach a certain point of critical mass where people are going to seek out the magazine based on who we’re talking to.
ANDELMAN: It seems like in recent years the folks interviewed in there, it’s broadened a bit, it’s gotten a bit younger at times. It seems like there’ve been some rap stars in there, maybe some film stars that maybe 20 years ago might not have quite qualified.
NAPOLITANO: That’s right. One of the things we used to talk about was that we don’t get Al Pacino and Godfather I, we get Al Pacino and Godfather II. In other words, somebody who’s clearly established themselves as having a strong track record. But in terms of actors, the movie industry has very much changed since then and with films being in theaters for about two weeks and then going to DVD, everything moves a little bit faster. The actors are a little younger and perhaps not quite as iconic. We had a great interview with Bruce Willis that we just ran in the July issue. And we all agree that Bruce Willis is somebody that was pretty high up on the list of guys that our readers liked. And then we scratched our heads a little bit and realized that this was the third interview with Bruce Willis, which was pretty extraordinary. It was quite an unusual thing to go back to him. And I think that’s because they don’t make stars like they used to. So we’ve adapted.
ANDELMAN: I read that that was the third time for Willis. Some people would probably scratch their heads and say, “You’ve interviewed Bruce Willis at length three times?” What’s interesting, it seems, about a guy like Willis is he’s always got something to say. This time I think the big takeaway was that he has changed political parties. And you got into that, and that was quite shocking thinking about how adamantly Republican he had been in recent years.
NAPOLITANO: We see a lot of the information that we publish in that long-form interview informs a lot of the coverage that Bruce Willis will get now for the next year or two. Any lengthy profile, everyone will use our interviews as a source and a sourcebook for various personalities. And that’s another thing that we are very proud of with the interview.
ANDELMAN: And I imagine that’s something that you look for, too, in terms of deciding who the interview will be. It’s someone who the public or the rest of the press will have to refer back to Playboy .
NAPOLITANO: That’s right. They’re gonna be able to speak on a number of different subjects in depth, coherently and in an interesting way. These are all things that we think about when we assign the interview. A taciturn guy is not necessarily the best thing for us.
ANDELMAN: It’s got to be someone who has something to say and is willing to say it.
NAPOLITANO: Right. Exactly, exactly.
ANDELMAN: Who are the big guests out there right now that you haven’t been able to get or, for whatever reason, have not been able to bring into the Playboy interview?
NAPOLITANO: Well, very often the hardest guests for us would be on the political side. I think that Hollywood responds very well to the kind of things that we do with the interviews. So, the guests usually come in Hollywood, it’s just a matter of time, when they feel that their project is right and that they’re willing to step out or that they want to finally let loose a little bit. So on the Hollywood side, I would love to hear from Angelina Jolie. On the political side, we’ve got a whole roster of political candidates for President out there. And I’m gonna cross my fingers and not really go into it too much, but we have had some good success with interesting some people in doing the interview for us, and as we roll out through the end of the year, you’ll see who they are.
ANDELMAN: I’m gonna take a guess, and I don’t expect you to confirm these, but I’m gonna guess that running for President, the three most interesting for your purposes would probably be Barack Obama, Mitt Romney, and maybe Bloomberg if he runs. I’m guessing that Hillary Clinton just probably will not do it at all. Has she been asked and approached?
NAPOLITANO: We’ve been in conversation with Hillary and Bill, so we know where they stand with us.
ANDELMAN: That would be a no?
NAPOLITANO: Pretty much, yeah. At this point. The idea is to kind of come around and make them have to say yes because everybody else is talking to us.
ANDELMAN: And what about in the literary area, the cultural area? One of the things that used to be fascinating to read is there were a lot of literary figures who would be interviewed in there, whether it be Norman Mailer, people like that. There doesn’t seem to be as many of those these days.
NAPOLITANO: I’ve kind of put on the slate that we should have our eye on John Updike for an interview. He’s a regular contributor to the magazine, but I think that he’s a shy guy and a shy public speaker. But he’s a very engaging guy, and I think that our readers would be interested, and it’s kind of funny that we haven’t quite covered him. Philip Roth is another guy that I want to bring in and land. Thomas Pynchon would be another person that I think would make headlines, perhaps a little bit off-beat for the bulk of our readers, but that would be another kind of literary find for us. But in general, the reason why you don’t see as many writers these days is when we look at the total package of the magazine, we’ve had extraordinarily good fortune in landing writers to write for us. So if we have them contributing pieces, we’re less inclined to try to find a way to get them in the magazine using the interview as a platform.
ANDELMAN: That makes sense. Of course, besides the interview, the other thing that Playboy tends to be known for is getting celebrity women to pose for the magazine. I’m thinking that’s the other big part of the equation in terms of if Playboy wants to make a big splash this month, it would love to have a big celebrity interview and a big celebrity photo spread.
NAPOLITANO: That’s right.
ANDELMAN: Is that a fair…?
NAPOLITANO: Uh huh, yep, yep, although we don’t tie the interview and photos together.
ANDELMAN: No, it’s just nice to have two big ones in the same issue.
NAPOLITANO: Absolutely, absolutely.
ANDELMAN: Two big features, pardon me. I don’t want to suggest I meant anything other than that. Again, there was talk in the last couple years that celebrities, women, were not as inclined to pose for Playboy as maybe they had been in the past, that they didn’t see it as the same path. Do you see that as true these days?
NAPOLITANO: Yes. I mean, I think that it’s a more complicated environment than it has been in the past. I think that, personally, a lot of celebrities would be more than happy to pose for us, but there are a number of people who have a lot at stake in their individual decisions. It’s not the same as when Sharon Stone and Philip Dixon decided to take some photographs. There’s a whole bunch of ramifications. They have endorsements, commercial endorsements, they have appearances at stake, and a bunch of advisors, and so it’s a really complicated process these days. And what we try to do is just reduce it to the idea that never mind the money, naturally the PR and establishing yourself and showing another side of yourself to the public is a major factor, and they should definitely consider that as a plus. But, also, it’s about taking a great photograph, a kind of photograph that will be seared in the memory of the national consciousness, and I think that’s something that doesn’t come up as often as it should in our conversations with them.
ANDELMAN: If the phone rings when we’re done, and it’s Angelina Jolie’s people and they’re calling to say, “Listen, Angelina would love to do the magazine, your choice, she’ll either do the interview, or she’ll do the photo spread,” which do you choose?
NAPOLITANO: Well, I certainly would choose the photo spread first. Absolutely.
ANDELMAN: Okay. So this is good. This is consistent with what I expected. I’m afraid I’d be disappointed if you said anything else, Chris. Who else would you like to have do a photo spread in the coming months to year?
NAPOLITANO: Oh, well, there are plenty of people. Anybody that is attractive and willing to embrace the sort of Playboy spirit and the Playboy lifestyle is on that list. It’s a great platform for reinvention and rejuvenation, so there’s a handful of young celebrities out there right now who are struggling a little bit or having personal struggles, and I’d see us as a great venue for them to kind of break out of that.
ANDELMAN: Let me guess. Lindsay Lohan?
NAPOLITANO: That would be one name.
ANDELMAN: Alright. Were you surprised at how upset Jessica Alba was when you ran a photo of her clothed on the cover of the magazine?
NAPOLITANO: Well, that’s a tricky area. That’s a tricky subject for us. Again, I think that it’s a group decision for when people embrace us or decide to cooperate with us. And it’s probably a group decision when there are upset feelings, maybe because other arrangements have been made for exposure for the personality or the celebrity that’s disruptive, or maybe it’s seen as a loss of control by the people who would like to be making these decisions for her. So, that’s about as far as I’ll go with that. I think this was more of a reaction by….This was not the way that people in Hollywood like to see things get done, and I think that the ultimate reaction to that was Jessica stepping out and saying that she did not want to be on the cover at the time that we put her on there.
ANDELMAN: Was that a political lesson for the editors of Playboy for going forward?
NAPOLITANO: I don’t think it’s anything that we didn’t necessarily anticipate. You’ve got the celebrity tabloids that are gonna run any pictures and any stories about the stars that they think will drive newsstand sales and entice their readers. Then you’ve got the glossies with Vanity Fair and others who have full cooperation from celebrities undoing things that are photo-driven essays with kind of bland stories attached to them. Playboy is somewhere in the middle between those two things. The interview is something where the only negotiation is, “Are you gonna do it or not?” And we’re gonna ask the questions and you can trust us to publish what you say and nothing but. That course has been really helpful to us because they are never surprised by what the story is about because they know what came out of their mouth. So the flip side of that is that when they choose Vanity Fair’s venue they know what they’re getting. They have no control over or some of the time when Us or In Style or In Touch or any of those books go forward with or let alone Star or any of those kind of things do it. And we see ourselves kind of in the middle. We’ll do what we want because, as mainstream as we are and as widely sold as we are, we have a little bit of an edge. There’s a little renegade quality to what we do.
ANDELMAN: One of the main things that’s different about Playboy today than it was in 1988 when you joined is the competition. For a long time, it was basically Playboy and Penthouse. It was Hefner and Guccione. Today, Penthouse is basically on the scrap heap of adult magazine history, and your biggest competitor, I think, in print at least, would seem to be Maxim. There was an effort the last couple years to sort of “Maxim-ize” I hate to use the term, but Maxim-ize Playboy a bit. My sense is that you guys did that, but gradually you’ve kind of even pulled away from that and gone back to more of the older Playboy style.
NAPOLITANO: Yeah, that was a very conscious decision based on what feedback we were getting from our audience and from young men. It’s very true that when it comes to female personalities and stuff like that, Maxim, in their cover choices, is a very close competitor to ours. They are a starter magazine for a lot of young men.
ANDELMAN: Oh boy. They’re gonna love that term. I like that.
NAPOLITANO: Oh sure. Well, they have been reinventing themselves three times a year in an effort to get away from that, but the reality is that you can attract a guy’s attention, but to hold it over the long term, which is what most magazines on the newsstand are about these days, they are in a place where they can’t claim newness anymore. You have to provide something substantial, and those are the kind of reactions that we were getting, that there might be short attention span stuff going on everywhere on the net or on TV or on video games or whatever, but the best service a magazine can provide is high-quality entertainment in print form.
So we look at the core of our magazine, the well, the interview, and everything in that as not easily mimicked or something that works best on paper right now. That’s the big draw, and that’s what we’ve dedicated ourselves to providing to readers, and I don’t think that anybody really matches up against us in that way. We’re a general interest magazine for men. We have a lot of content overlap with Esquire. We have a dedication to fiction which puts us in a similar place with The New Yorker. We go in depth with personalities who have given our interview which kind of aligns us and puts us in competition with Vanity Fair. But the package is unique to us, and we don’t want to mess with that because in that mix, which also includes jokes and cartoons, is the secret to why people stay with us so long. And I think that’s a lesson that will be learned by other people who truly want to compete with us.
ANDELMAN: I could see that there was a point a few years ago where Maxim was certainly the hottie on the block, and people were talking about it, and there’s rarely anything that goes over a page it seems like. But, Playboy , you open it up, and you expect to be engrossed in the stories, you expect to be reading it and turning the pages and following it and jumping to the back of the book to finish the story and to learn something. Maxim it seems like, by the time you get interested in it, the story is over, and then you’re on to the next thing. They used to talk about the MTV Generation years ago, with all the jump-cutting, the short attention spans, but maybe if you buy into what you said about it being a starter magazine, yeah, it gets you into it, if you’re a young man and you haven’t been reading magazines, certainly there’s eye candy and you start reading it, but it leaves you kind of empty.
NAPOLITANO: Yeah, I would agree. I think definitely we’re editors talking to each other, and we’re in a field where we’re curious, and we like to read and consume that kind of material. I’m not opposed to a guy going to a newsstand and picking up a magazine that is different from mine, because I think that it basically will spark something in them that they’ll draw a connection; if they ever get a look at Playboy, they’ll be favorably impressed. But they’ll be in the habit of looking at the stuff. And judging from what Maxim is doing, they seem to have gone heavily in the direction of service journalism, so they’re still kind of pitching woo to their marketers and their advertisers and providing them with a lot of face-offs that are similar in terms of content. But the flip side is that they really are kind of packing every page with a lot of consumable things. They’re keeping their guys up to date with a lot of products and gadgets. And we’ll have to see whether that’s gonna be successful for them. But they don’t seem to be showing any interest in personalities or articles or fiction, so it’s a different model.
ANDELMAN: Now, I mention that it used to be Hefner and Guccione were the guys that everyone equated with men’s magazines. Guccione, of course, is not involved with Penthouse anymore. Hefner, from what we read, what we see, he’s still there but not maybe as active in the magazine. My question really is, do you think there’ll be another generation of editors, perhaps like yourself, that will rise in the coming years and become associated with these magazines? At Esquire, David Granger is clearly connected to that. People kind of in the industry know that’s a David Granger product. It’s got his fingerprint all over it. Will people be talking about Chris Napolitano the same way or whoever takes charge at Maxim, or will these things still be, Hefner and Guccione, and then there’s not so much a visible personality beyond that?
NAPOLITANO: Yeah, well, it’s funny to say. Less so than Guccione and more so Jann Wenner. I think Jann and Hefner and their magazines and their products are kind of very similar, and they both invented these things. And I don’t know whether magazines and the corporate climate necessarily whether you’re gonna see magazine products that are identified with a personality like that. I would say that this is a Hugh Hefner product. I’m in there, and I’m making a lot of decisions about where we’re going and generating material, but for our company, there’s nothing wrong with the identification of Hef and the magazine and the Playboy brand. That just is. I don’t think that we could possibly get somebody else to do the things that Hef does for this company.
ANDELMAN: I’m glad you mention that because I want to ask you, what does, relative to the magazine, what does Hef have to do with the magazine these days?
NAPOLITANO: Oh, he does a lot. He is a very easy guy to reach. For as famous a guy and as much as he has going on day to day, I don’t know where he finds the time, but he dedicates two or three hours a day to the magazine. And that goes from everything of talking to our photo editors on the West Coast who are very close to him and nearby generating Playmate photography or working with our photo director, Gary Cole, on the major and minor photography or engaging in dialogues with our cartoonists and approving the work that they do, get a lot of different ideas coming across his desk, and he’s picking stuff for them to finalize.
ANDELMAN: Who’s the last hand on the magazine when it goes out the door, is it you or is it him at this point?
NAPOLITANO: I would give it to him, but I don’t quite know what that really means. There are three or four points when the material that we’re pursuing is passed before Hef for review. We pace out the magazine at the very beginning of the process before any work is even turned in. We basically know where things are going in each magazine. He might think that something is inappropriate or wish for us to improve it, but we’re probably on the same page with that. And then the work starts coming in, and it’s a lot of work, a lot of moving parts to this thing. And when stories enter the system, he’s going to get a read on it. When layouts are being built, they come out of Chicago and New York and go for his approval. Eventually, he has seen everything that goes into the magazine and given it the thumbs up, and then we have to make it all work. That’s really the last hand in terms of the detail work. If there are changes that come along or things that get adjusted, it’s just time to pick up the phone and fill him in.
ANDELMAN: And Chris, you’ve been sitting in the big seat now for I think about three years, I think we’re just about at three years, have you had a moment where he’s wanted to do something or something has come up, and you’ve had to say no to Hugh Hefner or you’ve had to take a stand and kind of say look?
NAPOLITANO: Yeah. In the three years that I’ve been doing this, I’ve been here for a very long time, he’s very clear about what he wants. He knows that he’s creating an atmosphere and a feeling. He doesn’t pretend to be inside the mind of a 30-year-old guy, but he pretty much wants to know what that 30-year-old guy should think of us. So using that, we generate a whole lot of ideas. In that time frame that I’ve been here, he’s spiked, I’d say, about three stories for admittedly good reasons, and this is where he and I both are approving it all on the process where, okay, you see it on the schedule or maybe it’s an iffy idea, but you really go through the whole thing, and then you’ve got two weeks before you go to the printer, and he says, “No,” usually in the humor or the more Maximy vein of things. I’ve had no problem pulling those pieces because he’s usually very persuasive in making his case. I’ve never told him or had to say no to any ideas that he has because editors, we have batting averages, and he’s got a very high batting average for what is successful for the magazine, and so we see it three months later down the line in showing up on the newsstand.
ANDELMAN: I would think that there are real pros and cons to being the guy who’s been there for 20 years and that you’ve come up from an editorial assistant to rise, like I said, to the big seat, that the pro is that you have this incredible institutional knowledge, you probably know where every paper clip is kept in the office. On the other hand, having been there all that time and started under this incredible publishing legend, and I’m not just saying it to suck up to him, he is an incredible publishing legend, and he’s a man who’s influenced an awful lot of things. But then suddenly, you’re in the position 20 years later of the other people in the organization turn to you when there’s a dispute, or if there’s an issue, they turn to you and say, “Chris, this is what we believe, and Hef may think this, what are we going to do?” It’s got to be a little challenging at times.
NAPOLITANO: It is, but the best thing is to keep the dialogue going. Hef is, first and foremost an editor, which is a very interesting kind of thing. He’s many things, and he’s had many roles here, and he’s been famous for 54 years. But, his love is the magazine, and his greatest knowledge is as an editor. I feel very comfortable with him, and I’m not going to stroke myself here, but I believe that we’ve been putting out a fantastic product in the last three years, and I’ve heard as much from him. He doesn’t like getting in a place where he is dictating material. He wants you to understand what he’s looking for, and he wants to get it, but when he starts shortening that leash, or when he starts feeling that you can’t give him what he’s looking for, that’s when people panic or start making the wrong moves. So you have to be as aggressive as you would be under anybody.
Every editor has a boss, and sometimes that boss is waving newsstand results or advertising results in front of your face. Hef is waving quality and instinctively knowing what he thinks Playboy should look and feel like.
So let’s go back to one of the stories that — I’m long-winded I know — but the one thing that he’s been very gracious about is one time I was saying yes to something that he was saying no to, and that was a very nice piece from a book called The Weathermakers. It was all about global warming, and we were ahead of the curve on that one, and he had some problems with the layout, and he really didn’t want to go forward with the piece, but I persuaded him to think twice about it. It was going to be a big topic, and he was very happy when our issue hit the stands and two weeks later, “60 Minutes” used the same kind of iconic image that we did, which was a polar bear on a tropical island, and then two weeks after that, Vanity Fair came out with their first green issue. So you do have to stand your ground and persuade him, this is why we’re doing this. And he’s very quick on the uptake, and so things move forward. So those are the kind of conversations you have with him.
ANDELMAN: Well, Chris, before we finish, I want to try something with it. Do you remember the movie Sophie’s Choice?
NAPOLITANO: Uh, I never saw it.
ANDELMAN: Well, the basic idea was that I think it is the Nazis, they are going to take, she has two kids, they’re going to take one of the two kids, and she has to choose which one’s gonna die. So this is your Sophie’s Choice. I’m gonna kill one of Playboy ’s most treasured features, and you have to choose which one to save. Is it the Playboy interview or the Playboy jokes?
NAPOLITANO: Oh, boy. Oh, I would…..Wow, wow. I’d kill the jokes.
ANDELMAN: You’d kill the jokes, okay. I’m not done. Now, the Playboy interview or the Forum?
NAPOLITANO: Uh, I’d kill the Forum.
ANDELMAN: Okay, the Playboy interview or the Playboy advisor?
NAPOLITANO: Wow, that’s another tough one. I could get what I get from the advisor in other places. I’d kill the advisor.
ANDELMAN: Oh, tell Chip Rowe I’m very sorry.
NAPOLITANO: Yeah, we’ll give him something else to do.
ANDELMAN: Alright, last one. Well, he is multi-talented. Playboy interview or the centerfold?
NAPOLITANO: The interview.
ANDELMAN: Ah, there we go folks. We’ve narrowed down what’s important in the magazine. Alright, last question. Chris, you’re married, and I understand you’ve got two children.
ANDELMAN: How does the editor of Playboy position his workday when he gets home at night?
NAPOLITANO: Oh, I got to let it go. I have to let it go. I don’t take notes as to what happens during the day. This is a very interesting job to have, but you can care about something too deeply, and I’m so happy and pleased with the editorial product that we put out. I don’t want to brag, but there’s nothing that I don’t like about what we put on paper for the magazine. There are a host of other things that I’m responsible for or in the middle of. If there are 10 things, I have to be happy. Success is defined by six out of those ten things being right, and I want ten out of ten, and that can be nerve-wracking. But that’s my problem, and I got to let that go.
ANDELMAN: Maybe I should have asked the question slightly differently. I think you’re 43?
ANDELMAN: Okay. You’ve got two kids, probably not too old, a wife, how do they explain what daddy does?
NAPOLITANO: Well, it’s kind of interesting. I have a daughter, and she’s older. I don’t think she’s at the age yet where her classmates might have picked up the magazine or found it. But they’ve been in the office, and they’ve seen, gotten glimpses of what we’re all about here. And it’s just a simple thing of like this is for adults. This is for adult men. Just like you’ll see me have a glass of wine during dinner, and you’re drinking juice. That’s just the way it is.