Cooper Hefner has assumed creative control at the brand his father launched 64 years ago as he brings nude images back to the magazine while lamenting the company's involvement in lowbrow licensing and reality TV: "Nudity hadn't been the problem — it was how it'd been presented."

It's true: Cooper Hefner, youngest son of Hugh and newly ascended chief creative officer of Playboy Enterprises, did enjoy a youth that was the stuff of teenage wet dreams. Celebrities and scantily clad bunnies wallpapered his life. He and his schoolmates could order anything they could think of, and the Playboy Mansion kitchen would send it right out. There was a private zoo.

Yet the good times came with a Freudian twist. His mom, 1989 Playmate of the Year Kimberley Conrad, hung in the library, depicted nude in a large portrait frame. "Yeah, that was weird," Cooper explains over lunch at the mansion. "It was like the elephant in the room."

The photo's long been put away. (Dad, now 91, divorced Conrad and dated a harem of blondes before rediscovering monogamy with current wife Crystal Harris.) But his son, 25, insists "the image being up now wouldn't bother me," pointing out that he recently requested Conrad pose again. "On Mother's Day, I asked her if she would be interested in reshooting her original cover," says Cooper. "Two weeks later we did it." (The image was published in June.)

Like Cooper, Playboy is grappling with the weight of history — how to refine a heritage brand as that heritage is up for debate across genders, generations and geographies. Cooper is leaning on the past as he plots the future for Playboy, a onetime startup turned conventional conglomerate — and a brand that fuels more than $1 billion in sales and recently was valued at $500 million — that of late has been beset by competitors and corporate malaise.

At the request of then-newly minted CEO Ben Kohn (who says the brand had "gone too wide and lost part of its aspirational quality" by "covering monster trucks and selling air fresheners"), Cooper returned to Playboy in June 2016 following an 18-month exile precipitated by boardroom battles over the company's direction. A key factor was a 2015 choice by Kohn's predecessor, Scott Flanders, to forgo nudity in the flagship magazine's pages in a bid for more mainstream respectability. "There was a lack of understanding of who we are," says Cooper. (He cites another mistake of the era: the decision to develop 2011's The Playboy Club as an anodyne NBC drama, which was canceled after three episodes, rather than an edgier version for premium cable.)

The magazine's March issue marked the return to the bare necessities — or at least to topless spreads. Cooper's fiancee, actress Scarlett Byrne (The Vampire Diaries), posed in one of them and penned an essay that framed her decision as a feminist act. The pictorials, which used to be kitschy high-gloss extravaganzas, now display an arty naturalism meant to connote a cultivated aesthetic. "Nudity hadn't been the problem — it was how it'd been presented," Cooper says.

"The audience was confused," adds Kohn, a managing partner at Rizvi Traverse, the private equity firm that since 2011 has controlled 70 percent of Playboy and whose other investments include SpaceX, Twitter and Snapchat. (In Hollywood, Kohn is best known for tending to Rizvi Traverse's since-divested interest in ICM.)

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Now the polished and self-aware scion, intent on sounding woke and mindful of the brand's eternal need to provoke (intellectually and sexually), is charting the course for what he hopes will be a more valuable and relevant Playboy. It's one that doesn't revolve around his old man (who is ailing and a semi-recluse) or dated totems of lothario living. "Creating something that resonates with my generation and the generation that comes after mine is how I'll measure my accomplishments," Cooper says.

"His father, when he started — the business succeeded because he found a way to uniquely speak to the young men of that time," says board member Dick Rosenzweig, who's been involved with Playboy for 59 years. "Cooper recognizes his father's intent, and he has a feeling for going about it as well — in his own way."

Cooper is quick to mark distance from his dad's notorious womanizing, but the two share many similarities, including deeply felt progressive politics. Cooper has thought of running for office but believes his affiliation with an adult entertainment company would likely render him unelectable. And both have a strong affinity for the armed forces. (Hugh served two years in the U.S. Army toward the end of World War II.) "I'm a liberal, and I have a real issue with the conservative side feeling like they own the military," says Cooper, who joined the California State Military Reserve in January.

Cooper began participating in board meetings as a nonvoting observer while still in college — spurred by anxiety about his father, who in recent years has receded from public view. (Contending with back trouble, the famously virile eponymous playboy doesn't want to be photographed strolling with his walker and fiddling with hearing aids.) "It's tough to watch him struggle, but I'm just happy it's physical and not mental," says Cooper. His father's oldest friends still visit for weekly dinners and film screenings, and he provides periodic notes on the magazine. (The elder Hefner was not made available to THR for this story.)

The mansion is quieter now, hosting a few parties a year (like one in April celebrating Amazon's docuseries about Hugh, American Playboy). Not long ago, the house was maxed out as a revenue generator, hosting a shindig a week, with business partners, potential business partners and random people willing to fork over the $50,000-a-night rental fee.

In a highly publicized deal, Daren Metropoulos, the 33-year-old heir to the Hostess Brands fortune, purchased the mansion in 2016 for $100 million, with the stipulation that the elder Hefner remain there until his death. Metropoulos, who has no ownership stake in Playboy, lives next door in a home he previously had bought from Hefner (and where Conrad lived until Cooper was 18).

Cooper, a child of ultra-privilege, is keenly aware of how he navigates his advantage. After attending the elite yet strict Ojai Valley School, he majored in film production at Chapman University in Orange County. He opted to pass on a legacy admission to USC, where his father has donated millions. "It made my heart feel better to go to Chapman," he says. "It didn't feel like it was given to me."

Still, he's not above working his gold-plated connections. He met Byrne six years ago after crushing on her as Pansy Parkinson in the Harry Potter films and then finagling an only-in-Hollywood introduction put into motion by friend Scout Willis, daughter of Bruce Willis and Demi Moore. "I thought, 'Wow, that girl's really pretty — I'm going to go on a date with her,' " Cooper recalls. (They live together in Marina del Rey.)

Not in the picture at Playboy is Hefner's elder brother, Marston, 27, who was initially positioned as a co-heir apparent. He's been out of the public eye since a February 2012 domestic violence incident in which Pasadena police were called to the home he shared with his live-in Playmate girlfriend, Claire Sinclair. Recently, he's been teaching English in Japan. "My dad was public about wanting us to run the organization together, but it became evident as we got older that it was not something that spoke to him," says Cooper.

Cooper regularly seeks counsel from another sibling, half-sister Christie, 64, who ran the company for more than two decades ending in 2009. "She can relate to the situation more than anyone could," he says. Christie often urges him to keep a clear head in business discussions: "For me as a 25-year-old, that's sometimes challenging," he admits. "My emotions get the best of me."

Also educational is what he saw as Playboy's lucrative but demeaning involvement with reality TV and lowbrow licensing. He thinks The Girls Next Door, the E! reality show that ran from 2005 to 2010, damaged the company long-term. "[The show] collected a young audience but didn't do a good job of conveying how Playboy is both playful and sophisticated," he says. Kohn adds that the series "brought the company down-market."

Such thinking has prompted Playboy, a branding vehicle with a magazine as its hood ornament, to terminate $15 million in licensing revenue generated at mall shops like Spencer's — a relatively small slice of the company's portfolio — in a bid to go upmarket. "We're not in the fuzzy dice business anymore," says CMO Jared Dougherty.

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The company is developing two projects with Brett Ratner's RatPac: a Hugh Hefner biopic (it's not known who will star) and a reboot of the late-1960s variety-talk mash-up Playboy After Dark. Says Ratner, with a director's eye, of the elevation of Hefner fils: "It's obvious, it's organic. He even has the looks of his dad — so much so it's bizarre."

Reality programming is out for now. Cooper claims to have been pushed into starring in a "mortifying" sizzle reel assembled by Gurney Productions (of Duck Dynasty fame) focused on his then-role as a brand ambassador. While MTV was interested, "I couldn't stand it," he says, noting the experience precipitated his departure from the company.

Meanwhile, the company's core video assets, including Playboy TV, which runs X-rated shows like Cougar Club L.A., have after years of management by internet porn behemoth MindGeek been consolidated in-house and will be overhauled for a 2018 reset. "These are areas of the business that are, from a cash standpoint, performing very well that have not been on-brand," says Cooper. "We need our story to be told with one voice across all platforms."

Cooper splits his time between content development and revenue opportunities ranging from branded nightclubs (one is in development in Manhattan) to apparel. "In China," muses Kohn, "we're viewed as an Americana fashion brand by the up-and-coming consumer; they've never truly been exposed to our media products because of censorship restrictions."

Meanwhile, the company has retooled its new-media efforts, which for a time were ramped up to compete with rivals. (Cooper admits Vice Media captured his demographic's imagination by feeling fresh and competing aggressively while Playboy was on cruise control, yet he notes that, now that Vice is backed by 21st Century Fox and Disney, "nobody is viewing them as some pirate ship any longer.") One of Kohn's first acts was laying off a slew of digital staffers in a turn away from pursuing what he feels were the diminishing returns of online advertising. As the CEO puts it, "the market had changed."

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It's what hasn't changed, though, that Cooper sees as his opening. He observes that the country has been reverting to a reactionary cultural conservatism remarkable in its similarity to the Eisenhower years when Playboy was founded. (President Trump is widely known to have venerated Hugh, but the feeling isn't mutual: "We don't respect the guy," says Cooper. "There's a personal embarrassment because Trump is somebody who has been on our cover.")

Cooper, sounding a lot like Dad, explains, "Yes, there are lifestyle components to Playboy, but it's really a philosophy about freedom. And right now, as history is repeating itself in real time, I want Playboy to be central to that conversation."

On another day, he's lounging on a sofa in the mansion's library, ruminating on the blessing and burden of his patrimony. His father is nowhere to be found, likely somewhere in this iconic Gothic Tudor-style manor, essentially finished telling the story he began in 1953.

Now it's Cooper's turn. "I suit up in my dad's pajamas for our Midsummer Night's Dream party; it's a nice note to the past," he says. "It would be a major mistake — ridiculous — to wear them to the office. I think about the Playboy philosophy constantly, but I have my own point of view. It's what will have to carry me through."

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ANATOMY OF THE PLAYBOY BUSINESS

Licensing

This is Playboy's biggest revenue driver. The company says a deal with global fragrance giant Coty tops $100 million in annual wholesale sales. Through a partnership with Handong United and Bally's, Playboy distributes clothing, footwear and fashion accessories globally, with more than a third of global revenue coming from China. Playboy is mulling a $25 million-$50 million capital raise for a renewed push into lingerie and swimwear.

Magazine

Founded in 1953, Playboy peaked with a circulation of 5.6 million in the 1970s and now distributes about 450,000 copies of each issue.

Television

After years of third-party management, Playboy TV and other video assets are being managed in-house. This year, more than 20 series, including some made by Playboy, were produced for the X-rated network, which is seen in 60-plus countries.

Digital

Playboy.com attracts roughly 4 million monthly unique visitors. (By comparison, Esquire.com has 7 million.)

Nightclub and Events

This year, a Playboy Club will open in New York, joining properties in London, Hanoi, Bangkok and multiple cities in India. The Playboy Jazz Festival, held at the Hollywood Bowl since 1979, sells about 35,000 tickets each year.

This story first appeared in the Aug. 23 issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.