I'm standing next to a row of Reagan-era cultural artifacts: an Indiana Jones fedora, a prop lightsaber, a Centipede arcade game. They're on display inside a dusty fabric factory in downtown L.A. that's been refashioned into an art gallery and, for one night only, a monument to nostalgia erected by Cooper Bradford Hefner, the semi-outcast heir of Playboy Enterprises and the youngest son of swing's eldest statesman, Hugh Hefner. His upstart media company, HOP (an acronym for Hefner Operations & Productions) is throwing one of its HOP Hangouts, which cater to the “cool geek.” Tonight, Hefner has created a pop-up '80s arcade fitted with some of the decade's most memorable props. 

“Nostalgia sells,” says Hefner with his wise-acre lisp, his face professionally painted to look like Bowie on the cover of Aladdin Sane. He emphasizes this point — and most of his points — by putting his hands in the praying position, as if he's pitching me his faith, usually his vision for Playboy, the company his dad founded in Chicago, in 1953. 

We're both a bit sloshed when we meet; I've been swimming in cocktails at an open bar when I see him gallivanting around his own party. “That's Cooper,” someone who might be his friend tells me. It's an old-fashioned, masculine name, like the surname of a grizzled adman you'd expect to be holding a stiff drink — not an iPhone. Hefner's a millennial, but I also imagine he has a fondness for his dad's generation. When we meet, the 6-foot-2 aspiring media mogul is a fast-talking salesman pitching me his worldview, which is as much dapper Playboy as it is 21st-century geek.

The frat boy inside me, a remnant from some Sigma Phi Epsilon party at UCLA in 2004, wants to ask Hefner where the Bunnies are. But that's a sensitive subject. Over the course of the last four years, Hefner has been at odds with Playboy's board of directors, which includes a difference of opinion on whether Playboy should have gone nude-less earlier this year. I ask him what he thinks about Playboy eliminating nude imagery. “I think it was a bad idea, the whole thing,” he says, “but we'll have to sit down and talk about this more.” Cooper Hefner is probably too drunk to get into it. I'm also not going to ask for a tour of the Playboy Mansion, which recently sold for $200 million to billionaire Daren Metropoulos with the stipulation that the elder Hefner can continue to live there until he dies.

When Hefner invited me to his Hidden Arcade, where I showered in '80s nostalgia, the only thing I knew about him was everything that had nothing to do with who he actually is: a 24-year-old with political ambitions, lots of opinions on Twitter and a vision for Playboy that could bring the brand into the 21st century. 

Reference: Hop's Hidden Arcade

Three weeks later, we're at HOP's low-key offices in a part of Marina del Rey that accommodates the spillover from L.A.'s famed Silicon Beach. Loaded on caffeine and playing table tennis, we engage in a coy back-and-forth between reporter and subject.

“I grew in Holmby Hills, man,” he offers, not recognizing that the upper-crust neighborhood's name doesn't immediately denote a connection to the Playboy Mansion. “I went to OVS, a small boarding school up in Ojai,” he says, while serving casually.

Cooper Hefner is the definition of sheltered, except he comes off as vaguely working-class, almost humble as he swings a ping-pong paddle in the storage room of his office. “I had a great childhood and I was always home on the weekends,” he says, subverting popular preconceptions about a boarding-school upbringing.

Home for Hefner was next door to the Playboy Mansion, with his mother, 1989 Playmate of the Year Kimberley Conrad, and his older brother, Marston. When he got older, he'd sneak into some of the hedonistic shindigs at the Mansion.

“We used to live on Red Bull and vodka,” he says. “When we’d walk out to the backyard, that's just what we did.”

The score is 3-0 (Hefner) and after he serves a bullet past my head, I realize the ping-pong balls have the HOP media logo stamped on them. How showy. Even when he's playing games, Hefner is an indefatigable salesman. He's winning the match as I ask him how he feels about the recent sale of the Mansion: “For what the circumstances are, it's the right move. The family that bought it will be stepping in as larger partners for Playboy. We just want to make sure the house stays a part of the larger business.” Cooper Hefner sounds like a budding politician, or uncrowned Prince of Playboy. 

Cooper Hefner; Credit: Courtesy of Cooper Hefner

Cooper Hefner; Credit: Courtesy of Cooper Hefner

Hefner began to work at his dad's company in 2012, when he was still attending Chapman University and studying film production and history (he confesses he wishes he'd majored in political science). But working for his dad wasn't originally in the cards. Now it seems to be his destiny.  

“I didn't want to work for Playboy as a kid; I didn't even understand the perception of it,” he says, now leaning back in an office chair with his legs crossed on his desk, his fingers locked behind his head. 

HOP media, which has branded itself as a new VICE catering to the “cool nerd,” as Hefner describes it, was originally going to be a section of Playboy online, its geek vertical, like VICE's Mothership, rather than a separate company. It was part of Hefner's quiet revolution to make Playboy cool again. 

Playboy went too 'bro-y,'” he says. “It was appealing to the frat guy, instead of doing a better job of catering to my friends, the creatives and current tastemakers of this generation.”

Cooper Hefner is a millennial who doesn't watch or play very many sports (unless you count ping pong as a sport). “If you ever want to shut yourself off to an intellectual conversation, talk about sports,” he says. HOP, for him, is a platform to engage millennials in an intellectual conversation, something he feels Playboy simply isn't doing: “Playboy's CEO just didn't get it, so I said fuck it and decided to build something with my friends.”

Right before this story went to press, I got a text from Hefner with big news: “HOP is moving under Playboy,” which essentially means mission accomplished. “I'm stepping in as chief creative officer at Playboy.” HOP's offices soon will close, and all its operations will be moved to Playboy headquarters in Beverly Hills.

Initially, though, Hefner was unable to integrate his ideas into Playboy because of pushback from the board. He and a partner invested $600,000 of their own money and started HOP in August 2015 (the website launched in January of this year) with six staffers who are all former Chapman University students or childhood friends of Hefner's, which gives HOP the feel of a tech startup.

The site posts about three to five pieces of content a day, and promotes the brand with retro lifestyle events around L.A., such as its '80s Hidden Arcade, Roller Disco nights and an upcoming celebration of Harry Potter's birthday on July 29. Tickets for these events are usually $40, which comes with an open bar. “The events are how we generate revenue,” says Hefner, who sees the parties as extensions of HOP and its nostalgia-thirsty demo.

Despite his determination to make his own way in the media landscape, certain aspects of Hefner's story make him resemble a modern-day Richie Rich character, a guy who can watch Harry Potter and decide he wants to date Pansy Parkinson, the bizarrely attractive Slytherin played by actress Scarlett Byrne, who's now his fiancée.

“Scout Willis was one of my closest friends growing up. And at the time, she was at Brown University with Emma Watson, so I thought that was my in,” he says of seeking out a relationship with Byrne. Hefner would spend the next five years courting Byrne on Facebook, which eventually led to an ice cream date in Cologne, Germany.

If I'm being honest, it annoys me that he could pull this off. 

Like a socially conscious 20-something who might fancy living on a houseboat one day, Hefner's wearing a pair of Toms alpargatas that make him look worldly. With blue skinny jeans and a T-shirt with a compass design on it, I wonder if this is how Hefner would dress if he was speaking at TED about his blueprint to rebrand Playboy as more VICE-like.

“People who are young don't view nudity as a problem,” he says. “I mean, Vogue today has nudity. The problem was how Playboy presented the nudity. But we'll talk more about that at lunch.” Hefner then wipes his sleekly side-parted hair off his forehead, like Don Draper after some classy sex, as his UberBlack, a chic Tahoe, pulls up to take us to lunch about a mile down the road.

Even though Hefner owns an Audi, he Ubers everywhere, like Ashton Kutcher.

In the car, he continues: “I wanted Playboy to have a voice on issues like 'Free the Nipple,' instead we were spending hours arguing about a pictorial on the girls Tiger Woods had slept with.” Cooper Hefner, like many from his generation, wonders why Playboy doesn't have a philanthropic monopoly on breast cancer awareness: “Talk about a relevant Playboy foundation.” I ask him if he thinks this would be politically correct, or if we live in a time where we can no longer talk about sex without being shamed for it.

“A real concern of mine, Art, is that we live in a time that's way too politically correct,” he says. “Nobody wants to debate anymore. I read a statistic that 66 percent of millennials would be open to limiting the First Amendment if it meant not hurting people's feelings.” The statistic Hefner is probably referring to was conducted by Pew Research in 2014 which revealed that “40 percent of millennials [are] OK with limiting speech offensive to minorities.” But his point is valid. 

Hefner says: “One of the reasons why I respect my dad so much was that he fought for the First Amendment. He spent his life fighting for freedom of the press, freedom of expression.” He sounds like a 21st-century version of his dad. 

Political discourse is Hefner's favorite pastime: “If I wasn't doing what I was doing, I would pursue a career in politics.” He tells me he'd run as a Democrat, and that he comes from a family of liberals. “I actually almost ran for Congress this past election in the 37th District. It's still something I want to do,” he says. Cooper Hefner tells me the environment would be the top issue he'd run on. I tell Hefner to wait 10 years. He's an obsessive Game of Thrones fan, which makes him the kind of guy I'd vote for. 

Reference: Donald Trump Is a Family Friend and He's Full of Shit by Cooper Hefner

Cooper Hefner as David Bowie on June 4; Credit: Courtesy of Cooper Hefner

Cooper Hefner as David Bowie on June 4; Credit: Courtesy of Cooper Hefner

Like his father before him, he occasionally parties in a silk robe, which is brand-appropriate, something his troubled older brother, Marston — arrested for assaulting his Playmate girlfriend 2012 — is known for distancing himself from. Cooper Hefner is his father's son; he's Bruce Wayne in Gotham, who's staying true to his father's vision but always looking ahead to the future. Like the young and ambitious heir to Wayne Enterprises, he's been at odds with the old guard. 

He explains, “I used to go to the board meetings until Scott Flanders and I had a big fight one day.” Flanders is a sort of modern-day equivalent to John Sculley, the guy who almost destroyed Apple in 1993. He's basically the square who replaced Christie Hefner, Cooper's older half-sister, as the CEO in 2009, as the first non-Hefner running Playboy (which was a mistake). In May of this year, as the company began to explore a possible sale, Flanders resigned. Board member Ben Kohn is now the CEO, and Cooper Hefner remains as a sort of Steve Jobs figure who's both an irritant to the company's board of directors and potentially a game-changing partner.

HOP offices in Marina del Rey; Credit: Photo By Art Tavana

HOP offices in Marina del Rey; Credit: Photo By Art Tavana

After a short sojourn at a colonial-style Starbucks on National Boulevard in Santa Monica, which has a fucking fireplace, I reconvene with Hefner and a few of his friends at a local sports bar near the Marina, not too far from Hefner's private residence (which he shares with his fiancée). We begin to talk about everything from Scientology to Sarah Palin. I discover that Cooper Hefner has a problem with the meat industry even though he isn't a vegetarian. “I have family members from Alabama on my mom's side, but I have a problem with hunting. [But I] appreciate someone that hunts and eats the meat, rather than someone who goes to the supermarket and is completely detached from the process.” In other words, Cooper Hefner is against hunting for sport but sympathetic to the idea of hunting for survival or to connect with one's prey (or dinner). We're in agreement on this. 

We then talk about Snapchat filters, which confuse me, a lot. “It was one of the first times I truly felt old,” says Hefner, referring to the first time he was introduced to filters like “face swap,” where two Snapchat users can pretend like they're John Travolta and Nicolas Cage in Face/OffJeremy and Katrina, the latter of whom is wearing a Chapman University T-shirt, are his two best friends and they've helped him run HOP. They join us for a beer as we discuss Elon Musk's simulation theory. Here's Hefner's theory: “People have really become detached from living in the now.” I ask Hefner if his dad likes to tweet. He humorously quotes his dad: “I used to be a jitterbug, but now I'm a Twitter-bug,” which is really fucking cute. 

We're drunk and talking about politics, which is exactly what I wanted to do with Hefner a month earlier at his Hidden Arcade. 

“Not talking about politics is bullshit,” says Hefner on a major beer buzz. I ask him who he's voting for. “Hillary,” he replies, resolutely.

“Look, I think a large issue people have with Hillary Clinton is that she's a woman.” He later adds, “But if I could choose one politician to get fucked up with, it would be Sarah Palin.”  

We begin to discuss how Katrina's friends on Snapchat are too vapid to understand what Brexit is. “She gave me a tl;dr [too long; didn't read],” says Katrina, giggling at a Snapchat user who doesn't know who Justin Trudeau is. Cooper interjects. “Who doesn't fucking know who Justin Trudeau is? He's making politics relevant.” 

Reference: 19 reasons why the world has fallen in love with Canada's prime minister Justin Trudeau

We've now had enough to drink that I'm trying to convince Hefner to come get audited with me at the Scientology Celebrity Centre. “Scientology fascinates me because it's an example of why we should be critical of religions that have been here for so long.” At times, when he's trying to carry the conversation, which is always, Hefner sounds like a young Bill Maher on Politically Incorrect: “Anyone who is close to the Obamas knows they're either agnostic or atheist, the same with the Clintons, but the general public is not ready for that.”

In 2012, a year before launching HOP, Gurney Productions approached Cooper Hefner with a deal to be the star of his own reality TV show. MTV and VH1 made offers. Hefner declined every single one of them. “It was one of the best things I almost did, but that I never did.” Here's why:

“I remember how The Girls Next Door had become the largest explanation of what Playboy represented, which cheapened it. Like Playboy was just this guy hanging out with these girls. I was fucking horrified when they started shooting it,” says Hefner, who was 11 when the reality TV show was filming at the Mansion. “I remember looking through my dad's scrapbooks and feeling confused that a reality show was representing his company. I didn't want that to be my generation's perception of Playboy.”

HOP is Hefner's strategy to build a component that can modernize the Playboy operating system. They're working on a graphic novel, features on sex workers and asexuality, opining on Brexit (from the millennial's point of view), working with roughly 100 freelancers and attempting to inhabit a space owned by VICE, which Playboy seems light-years from infiltrating. “I just got tired of sitting in a board room and having 40-, 50- and 60-year-olds telling me what my generation was into. I was like, 'Why don't you just ask people my age?'” 

In the background, I can hear Empire of the Sun's “Walking on a Dream,” a song that almost exclusively appeals to ambitious millennials who drive hybrid Hondas. Frontman Luke Steele sings: “We are always running for the thrill of it thrill of it/Always pushing up the hill searching for the thrill of it.” For Hefner, the ultimate thrill is making Playboy cool again, like Steve Jobs returning to Apple when he sold NeXT Software to the company he founded for $400 million and made it the trendiest company on the planet. 

Cooper Hefner, like any millennial, is looking to be his own man in a world that's evolving at a rate where the very definition of “man” could be something different for the next generation of Playboy readers. A few weeks later, Hefner invites me to the Moonlight Rollerway in Glendale for what could be one of HOP's last independently run roller disco “Hangout” events. It turns out his quiet revolution is now a cultural revolution he'll be waging from within Playboy.

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