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The Hundreds X Playboy Interview: Cooper Hefner by Bobby Hundreds

The Hundreds X Playboy Interview: Cooper Hefner by Bobby Hundreds

What does Playboy mean to you?

Perhaps it means tawdry centerfolds, the universally recognized bunny logo, or The Girls Next Door reality show. Maybe it means Hugh Hefner in a bathrobe, dreamlike parties in the grotto at the foot of the Playboy Mansion. To some, who read the magazine “for the articles,” Playboy means world-class editorial, high-profile interviews, and literary power. And if you’re one of our teenaged customers, maybe the extent of your Playboy knowledge runs to Supreme and Anti Social Social Club collaborations.

Playboy means all of those things to me and more. Playboy was the first time I saw a naked woman (I guess that makes it my first vice). But, throughout the years, Playboy also introduced me to important cartoonists like Jules Feiffer and Harvey Kurtzman. Playboy championed fictional storytelling by Michael Crichton, Updike, and Vonnegut. Above all, Playboy became this globally recognized brand with a rich heritage. To me, Playboy embodies the American spirit in a way so few have been able to achieve. And they’ve done it by remaining true to their core principles, even if that means speaking out, even if that means in defense.

This afternoon, I sat down with 26-year-old Cooper Hefner, Chief Creative Officer of Playboy. With the passing of his father, founder Hugh Hefner, and with his sister’s stepping down as the head of the company, Cooper recently picked up the torch. It’s crazy to me, how print is dead and the political climate is so rife with landmines, yet Playboy—a business defined by nude photographs of women in a magazine—is stronger and more sensible in 2018 than ever. So, I asked Cooper about that. How Playboy navigates it all so smoothly and continues to evolve and grow. And what his plans are for the next generation of Playboy.

BOBBY: For the younger generation of kids out there, their appreciation and understanding of Playboy is different than someone like me. I was around in the ‘80s, I grew up on it. I feel like that’s how I became a man—by reading Playboy. And these kids, they don’t really have the same context or appreciation for Playboy. So, how would you explain what Playboy is to them in 2018?

COOPER: I would explain that Playboy is the same thing to them as it is to a 30 or 40 or 50 year old. Ultimately, it’s a representation of freedom of expression, a celebration of sex, a celebration of life. And that philosophy has existed at the core of the brand since its inception.

Certainly, for a younger generation, there seems to be a desire to interact with the brand. I find it remarkable that we are an adult company—so we target adults—but it is fascinating the interest that the younger generation has with some of our collaborations. Whether it’s Supreme or Anti-Social Social Club. We had a fragrance business with a company that made over $100 million a year in revenue and a large percentage of the consumer buying the product was teens. For me, I take a step back and find it absolutely fascinating that the rabbit—for whatever reason—and Playboy is a part of the psyche of this next generation. Certainly there is a detachment from understanding what the brand stood for and really fought for. And that’s something that the content team and the creative team here strives to make sure we’re doing a good job of communicating effectively.

Considering the sensitive climate around women’s issues, I feel like you guys are navigating that conversation really smoothly while not compromising any of your brand integrity or whatever Playboy has stood for. I don’t feel like you apologize for anything, I don’t feel like you feel the need to apologize for anything. So can you discuss Playboy’s longstanding history around women and sexuality, and what it means to celebrate that sexuality?

When I’m asked if Playboy’s a feminist brand, I have a tendency of erring on the side of caution, because feminism has so many different sides to it and different meanings. If we’re defining feminism as the right for a woman to decide to choose the life she wants to live, then absolutely I’m a feminist and Playboy’s a feminist company. And that really is ultimately a principal idea of what makes the brand Playboy.

The notion that men should be able to comfortably own their sexuality and talk about sex and dress and look the way they want to, yet, for whatever reason, the moment a woman does it, it’s a negative? That is fascinating to me. And then we have a tendency for criticizing women for deciding to go down the road of professionalism as well—I’m saying traditionally professional. If a woman doesn’t want to celebrate her sexuality or doesn’t want to find a way to pursue a career where she’s owning her femininity and beauty, but wants to do something that’s buttoned up and a little more traditional, women get the brunt of it on both sides. So it’s strange to me.

“[Playboy is] a representation of freedom of expression, a celebration of sex, a celebration of life.”

I really do feel—and this, I think, would enrage a lot of women and men who don’t necessarily understand what Playboy means—but, I really do feel as though attacking Playboy is attacking women. Because it really does come down to the idea that men and women should both be able to own their sexuality comfortably. So much of the news cycle is about violence and aggression and hostility towards one another. The brand, for over six decades, has consistently tried to celebrate sex and life and relationships and romanticism. And for whatever reason, that’s pissed a lot of people off. And it’s celebrated specifically from the heterosexual male point of view for the most part, which is also pissing people off—today, specifically. And that’s fascinating to me.

I feel like Playboy has always pushed people’s buttons but do you feel the buttons are being pushed differently now?

I don’t. I mean, it’s hard for me to say because I wasn’t there. Looking back in history, I think there were a number of movements, specifically the second wave of the women’s rights movement, Gloria Steinem and some of the other influencers that really pushed for women’s liberation and really—in a lot of respects—made Playboy the enemy. And what was always interesting with that particular movement was, and I think Gloria Steinem—I have a tremendous amount of respect for her. She did what was really important and that was to say women are not just sex objects. That the idea is, that women have a place in the work force that goes beyond what they look like.

100%. Playboy never advocated on behalf of the opposite. We just also said men and women, both, to each other, to a certain extent, are sex objects. That doesn’t mean there’s not more to us. It just means that I wear particular clothes, I take time in how I style my hair, I want to look presentable and attractive to my fiancé. I like to feel good about myself. Is that not something that both sexes should celebrate? There was a detachment from that.

Interesting. And speaking of women, when I walked in here, it seemed like almost everyone working here is female! I was surprised...

There’s a lot of women in the Burbank offices, there’s a lot of women in the New York offices, there’s a lot of women who work for the company. And again, I think really what it comes down to is that it’s really hard to have a conversation with someone who’s already made up their mind with Playboy. A lot of times it really does show someone’s uncomfortableness with sex and arousal more than it says about Playboy.

I agree with that. So, obviously with your father’s passing, all eyes are on you and I feel like Playboy is in this new transitional phase. You have taken over—what are your plans personally for the brand and the business? Is it going to change?

So if you take Vice and put it at the center of a table, you know the nine people that are going to come and interact with it, for the most part. They’ll maybe have Hawaiian shirts and prescription glasses they may not need. If you put Complex, you know the type of guy and gal you’ll get. When you put Playboy at the center of a table, a lot of times the organization as a whole appeals to a psychographic rather than a demographic. So, you’ll get, similar to the [The Hundreds “Stay Hungry”] dinners you’re putting together, you’ll get a liberal CEO and also a member of the LGBTQ+ community, you’ll also get a staunch Trump supporter. And it makes for just fascinating conversation. From a creative standpoint, step back and say, “Wow, we really have the ability to exist in a lot of facets.” How is it that we can exist by putting a Playboy jazz festival together and create a space for a 50+ black male and female, yet also put a brand together that really resonates with somebody completely different? At the Pride parade... Now, I’m not saying that there’s not spillover. It’s very different demographics for the most part, but not entirely different psychographics, which is what’s very cool about the brand. From my point of view, the brand has gotten much larger than I think anyone, than certainly my dad, had ever anticipated.


Yeah, he spoke about that! He and I spoke about it. He’s done interviews saying that in his wildest dreams he never assumed that Playboy would become what it has. So my point of view is really just giving people in all these different areas (not just in terms of the world, but personality archetypes) permission to comfortably own sexuality.

It’s not just for the heterosexual male anymore. There is a massive LGBTQ+ community that has adopted Playboy as one of several beacons of sexual liberation for their community. I take a step back and say, “Okay, so what does that mean for us as a brand?” And, you know, really there’s a tremendous amount of opportunity just to say, “We’re going to protect the larger mothership of the company,” which is the rabbit and the IP, but there is an opportunity to bifurcate and create these channels that speak to a younger audience that do exist in these different bubbles.

So another reason I wanted to work with Playboy was because of what its accomplished as a brand. When you think of Playboy, it conjures up so many images. For me, it has to do with your dad [Hugh Hefner] and the lifestyle and a certain era of American life that I glorified. I wasn’t really around for it either but everything was swanky. There was an allure and romanticism to Americana. So, what did your dad do right in creating this legacy, even if he had no intentions of getting this far? Especially considering the newer brands of today, who can start something in 2018 and achieve the same success? In 50 years, are we going to be talking about the cultural impact of Tesla or an Uber? 

I didn’t say that my dad didn’t think it would get this far. I wasn’t clear. His interpretation was that it was never something he believed would get as a big as it did. He always said, “I always wanted to publish a magazine that paid for itself and just paid for me to be okay.” It obviously manifested into something much larger.

He found a hole in the marketplace that was much larger than I think he assumed. Which was that there was a desire for people to pair sophisticated content with sex and that sex was not something that people wanted to view as taboo. And that there was a yearning in the ‘50s for that to be pulled out of the closet. And that’s really what he’d gotten right along the way. In the same way we started this conversation off around democracy, we’re talking about a time in American history—the mid 20th century—when individual freedoms were being challenged with McCarthyism and Hollywood being branded as a communist safehouse essentially. And there were writers and entertainers that were being blacklisted and weren’t working. Playboy sort of built itself as this rebellious vice brand with a bowtie. That was really interesting. That was something that really sung to so many Americans and it ended up appealing to the world in the same way that American values continue to appeal to the world.

“I view Playboy as a brand… that has historically fought for civil liberties and individual freedoms. So when those values are challenged, we step up to the forefront and engage in that fight unapologetically.”

I always find it just fascinating when I travel internationally, although different markets interpret the brand differently, we have a lot of different products and various digital platforms, and licensees in various countries, that there still is an understanding that Playboy—from a brand awareness standpoint—is one of a couple brands that represents Americana to the international community. And that is just a testament to my dad’s marketing brilliance, something I admire tremendously. And I also think that in a lot of respects it’s wild. You had said that there was an era of American culture and history that really spoke to you and I feel the same way. What’s amazing is that I think the rest of the world feels that way. Think about the figures and brands and the messaging that came out of that era—specifically the ‘50s, ‘60s, ‘70s—so iconic. And nostalgia has impacted specifically that period of time. It’s impacted style and music and lifestyle and politics to a certain extent in ways that I don’t even think we’re aware of today.

So speaking of which, Playboy has never shied away from voicing its opinions on political matters. This comes up more and more, the discussion on whether brands should stick to selling a product, instead of speaking on politics.  

I’ve never understood that. That’s just my philosophy on branding; that it should be so intertwined with who you are as a person, that there should be no distinction. I want to understand everything about the brand I’m supporting—like who am I giving money to? What do they believe and would I agree with what they’re doing with that money? That’s my dollar, you know? I want to make sure it’s going to the right place. Don’t lie to me. Don’t pretend to be something you’re not just to take my money. I feel like it’s dishonest in a way. What is your—and Playboy’s—philosophy on intertwining politics with branding? 

I absolutely understand why a fan of a brand, or a fan of an individual, or somebody who just enjoys following someone else or a company’s happenings, would have an issue with one taking a particular stance on politics because a lot of the time, the world is heavy for a lot of people. And people want to find something to escape in to. So I completely understand that.

From a philosophical standpoint, my beliefs are in line with yours. I actually do believe and have an interest in knowing where my dollar goes. But I also have a tendency in believing that if you have the ability to influence one person, you have an obligation to do the right thing. I can’t think of a more appropriate time (although I’m 26, I’m pretty young—looking back at a time before me, as well as now) as individuals as well as companies to be speaking up for what’s right. I couldn’t imagine staying quiet with what’s happening right now. Those are interests that I have: a sense of fighting for people who don’t, who aren’t allowed, who don’t have a soapbox. Or those who don’t have as loud of a voice or have the opportunities that I have (which is why you [Bobby] talk about it so much).

I recognize the desire for folks to escape. I think that’s something that a lot of actors and actresses have a tough time with, you know? Where, for whatever reason, they’re held to a different standard than musicians and a lot of brands. There’s a lot of actors and actresses who want to say different things, but don’t, because they worry that it will impact the public perception of them. If I sit down and watch a Leonardo Dicaprio movie, am I going to see a guy who’s fighting for climate change? And if I’m someone who doesn’t agree with climate change is that going to impact the entire story? I mean, that’s different. It’s a different world. For me, I would say I don’t view Playboy as a political brand by nature, in the sense of covering politics. I view Playboy as a brand, really we are a brand, that has historically fought for civil liberties and individual freedoms. So when those values are challenged, we step up to the forefront and engage in that fight unapologetically.

Why does the world need Playboy today? 

I think Playboy’s in a unique position where it reminds people of who we were. And if you don’t know who you were, then you don’t know who you are. I also believe that it’s not just about the world needing Playboy, it’s about the world needing people and companies and non-profits and institutions that are standing for the values that Playboy stands for which, at the end of the day, is freedom. What we should work towards is finding a way where we can get to a place where we can protect our neighbor while understanding that they should be able to make the decisions they want to whether or not we understand those decisions. That’s a really tough place to get to. Most of the fighting that happens in the world is caused by either resources we have an interest in or trying to direct other people’s lives in a way that makes sense for us rather than them. That is what makes Playboy inherently American. Because we’re a company that, as long as I’m here (and I don’t intend on going anywhere), we tend to have the company stand for those values.

Did you think that you were going to take this Playboy one day? When you were growing up, seeing all of this, was this something that you thought you were going to do? You have other siblings, right? 

I do. My sister ran the company. She was our CEO for over 20 years. And then she stepped down in 2009 and then an individual named Scott Flanders stepped in. He and I did not get along [laughs]. I was young. He just had different interpretations of what the brand and company should represent.

So this was on your mind, even when you were younger.

I don’t know, it’s hard to say. I don’t know how to jump back into my 14-year-old mind and evaluate whether or not this was actually something I wanted to do. I know that when I had transitioned from my later teens and then I was 20 and really learning about the company, I became really interested in it. It was just simultaneous—there were two things that were happening. I was fascinated with both my parents. That just happens I think at a certain point. You become interested in self and understanding why your parents are the way that they are and starting to think more similarly to them. And then that sort of was the journey to learn about the company

For me, it was learning about the past and learning about what made Playboy iconic and matter to generations before mine. I became really interested in helping guide the company back to that because, from my point of view, the Girls Next Door and really what the company was representing—although that was wonderful from the point of view of constructing a story to appeal to another generation—it lost the sophistication from my point of view. And that was something I wanted to be a part of reintroducing.

“Playboy’s in a unique position where it reminds people of who we were. And if you don’t know who you were, then you don’t know who you are.”

Was there ever a point in your life where you rejected it? Not being interested in anything your dad had accomplished?

No. It sounds ridiculous and I’ve never said this because I’ve never wanted to come off as entitled and I hope this doesn’t read wrong. But, everywhere around the house was that bunny. That bunny was there. It was almost branded in my own psyche as like, a family emblem—a family crest. In certain respects. It sounds like a silly thing to say but it was on the notepads in the house, it was everywhere. There wasn’t ever a sense of, “Oh that’s the company. That’s it.” You’re growing up at the mansion. The perception of my dad when he was walking around wasn’t like, “I’m going to go to work and be the CEO and come back and be the father.” You’re getting dad, who’s Hugh Hefner, 24/7. I think that really caused me to interpret it not only as a company, but “This is my life.” Even though I talk about it like, “Do I want to go into the family business?”—that’s not really how I perceived it. I just thought, “Okay, well...”

“This is my life. That’s my name.” That’s your name.  

Right. Which is remarkable but also creates a really unique work environment. A lot of times when you’re talking to senior executives or other folks or partners, you’re holding the brand to a standard that others don’t. “If that’s not good enough, it’s ultimately a reflection of my family.” It’s a reflection of me. Which is just a weird exercise I do—but you (Bobby) can relate to that.

Yeah. Employeesat the end of the day they go home and can go back to their lives. Or, they may not work here at some point, they’ll move on, but you’re stuck with it. It’s your name, it’s my name. Ben and I, we want our kids to take The Hundreds over. I want a brand like Playboy. I want to be around 50, 60, 100 years like Ralph Lauren. And when they do, I hope they feel like how you’re talking about your dad’s brand right now. “That’s my family crest, that’s my name, that’s my dad’s reputation,” you know? Even after I die, I hope they continue a good job of telling my narrative as well as the brand’s story.


The Hundreds X Playboy releases June 28, 2018.

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