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playboy limped into the 1980s with its circulation damaged, its prestige diminished, and revenues in free-fall. Though Hugh Hefner was still appearing on programs like Playboy Roller Disco, the brand largely drew funding from Playboy Club London. At the turn of the decade, American Playboy tells us that the club alone was responsible for 85% of Playboy’s profits, which was nice but unsustainable should anything bad happen to that revenue stream.

The London club was humming like never before: A July 1979 celebration of Playboy’s 25th birthday featured 8,000 bottles of champagne, 500 bottles of whiskey, all consumed on a fairground over the course of 25 hours.

“I earned $1 million a year, I lived in a penthouse above the club,” Lownes told the Sun much later. “I was the highest-paid executive in Britain, in the Guinness Book of Records for my salary. Did I deserve it? Does anyone?”

The disaster came to pass when the Playboy Club London was accused of violating British gaming laws and subject to a series of simultaneous raids and seizures on February 20, 1981. Victor Lownes had been living the high life, partying with people like The Beatles, Sean Connery, and Michael Caine. But the high profile attracted jealousy and bad feelings.

As American Playboy tells us, the charges against Playboy Club were trumped up. A rival casino was attempting to poach the Club’s high rollers illegally. Victor reported the rival, which was forced to close, but the bosses of the other casino told the cops that playboy had been illegally extending credit to gamblers. The clubs were raided and their licenses temporarily suspended, pending legal resolution.

With another extended reenactment sequence, Hef understood this to mean that if he fired Victor (played by New Zealand actor Emmett Skilton), he would be able to keep the license. He sent three men, including company president Derick Daniels, to send Victor packing. They did so in April, but to no avail. The clubs had their gaming licenses revoked and were forced to shutter their doors for good that same year.

Though the blow to the empire was major, the show tells us that Hef thought the brand could pivot to their Atlantic City property and keep on humming. But the New Jersey Gaming Board didn’t look kindly on Hef’s admission that he had bribed the corrupt New York Liquor Board many years earlier, when the Playboy Clubs were first opening. The clubs, which had been operating under a temporary license, were also forced to shut down.

Hef with daughter Christie. Bettmann / Getty

As a result, the show says that Playboy lost a whopping $50 million in 1982 alone. Hef knew it was time for a change. That change came with a familiar face: One of the talking heads of the series, Christie Hefner, was elevated to president, replacing Derick Daniels in that same year.

Christie’s first moves were to trim away some of that fat. That meant closing Playboy Clubs and continuing the move away from movie and music production. One of her early innovations was to launch the Playboy Channel, a pay-TV network that allowed Hef and the company to connect with the viewing public in ways they never had before. That included ample nudity and a lot of the signature Playboy wit. The channel was broadcast only 10 hours a day, from 8p.m. to 6a.m., before switching to a 24-hour format in 1994.

Despite her best efforts, the company still teetered on the edge of bankruptcy in 1985. So they needed to change editorial strategy. That change came in the form of featuring celebrities on the cover of the magazine. Early favorites included Madonna, Bond girl Kim Basinger, and Wheel of Fortune presenter Vanna White.

The show tells us that one of the most important nude celebrities of the decade was one playboy turned down. Vanessa Williams was the first Black woman ever to win Miss America when she received the crown in 1983. But a photographer from her earlier days had been shopping around naked snaps of the beauty queen. They had been offered to playboy, but as Hef says: The magazine wasn’t about to ruin the life of a pioneer. Naturally Penthouse bought the rights and published them, leading to its highest-ever circulation.

playboy’s streak of taking on important issues of the day did not stop with Christie Hefner’s ascent to the head of the company. The magazine covered the AIDS epidemic tirelessly, including this interview with the actor and playwright Harvey Fierstein that ran in August 1988.

Fierstein’s candor, as the disease claims more and more of his friends, is heartbreaking.

“Traditionally, throughout history, each generation has had two periods of loss,” Fierstein told playboy. “First, almost every generation has had its war, because as long as there have been heterosexuals, there has been war. People die. And then, of course, there is the period when one’s friends and acquaintances grow older and die.

Hef and former wife Playmate Kimberley Conrad with sons Marston and Cooper. Ron Galella, Ltd. / Getty

“But we, in our time — particularly those of us in the gay community — we have had a minimum of four periods of loss. We had Vietnam and we had our normal cycle of aging to look forward to. But we also had drugs. I lost a lot of friends to drugs. Some others, if they didn’t actually die, fried their brains, and aren’t much good now. Now we have AIDS, before going on to lose everybody else. It is incredibly unfair.”

On the cover of that same issue was a young woman that would become very important in Hef’s life. Kimberley Conrad made quite the impression on Hef, covering the magazine before becoming Playmate of the Year in June 1989. She and Hef were engaged by that point and married the next month. Kimberley and Hugh Hefner had two kids together, Cooper and Marston, in 1990 and ‘91, respectively. (Cooper, like his big sister Christie, has since risen through the ranks at the company.)

Kimberley and Hugh remained together for nine years, until the show tells us that she was unfaithful. Though they separated in 1998, Hugh bought the house next door so she could raise Cooper and Marston in close proximity to their father. The couple remained separated until 2009, when Hef filed for divorce, citing irreconcilable differences.

“I would’ve been happy to divorce her when we separated, but she wanted to remain married for our boys,” Hef told People.

During that time, Hefner returned once again to his bachelor lifestyle. The show speeds through the '90s as Hef takes a step back from editing the magazine and became much more of a celebrity presence. The Friar’s Club Roast of Hef took place in 2001, which was essentially a victory lap for the mogul. He’d proved everything he ever needed to prove.

In 2003, the magazine celebrated its 50th anniversary with a special issue. Highlights included 20 Questions with now-Senator Al Franken and Jack Nicholson sitting, at long last, for his Playboy Interview.

One of Nicholson’s responses seems like it could have come straight out of Hef’s mouth.

“I don’t think I’ve ever been cynical about love, though we 1950s guys had a hard time making that transition into the 1960s ‘I love ya, man.’ We thought love was a more sacred word. What can I say about love? In my life I have had more of it than I expressed. There’s no doubt about that. One of the best definitions of it comes from Bertrand Russell, who said, ‘There is love, and everything else is staring into the abyss.’ You feel better when you’re expressing love. I have often heard people confess, “I’m hoping for one more really big romantic experience in my life.” We want that feeling. You don’t forget that exhilarated state. It’s an exalted state, though I’m not the guy who should be saying this.”

After 2003, there were still a couple major landmarks left in Hef’s life. First was the Girls Next Door. The E! show brought viewers into day-to-day life at the Mansion. Though the expectation was that mostly men would tune in, American Playboy tells us that the show appealed mainly to young women. The one who stood out, both to viewers and to Hef, was Crystal Harris. She and Hef met in 2008, she appeared on a single season of the show, and they married in 2012. They remain married to this day.

Hugh Hefner with wife Playmate Crystal Harris celebrating New Year’s Eve 2014. Elayne Lodge

Though Hef sold the Mansion for $100 million a few years ago, he worked out a deal to reside there until he’s no longer able. He’ll turn 91 on April 9. Cooper, Hef’s son from his marriage to Kimberley, serves as the magazine’s Chief Creative Officer and public face now and for the foreseeable future. And the story, up to now, is still being written.

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