What would be considered unusual almost anywhere else—women walking around in fishnets and bunny ears, a pajama-centric dress code, multiple twentysomethings sharing an octogenarian boyfriend—was the usual at The Playboy Mansion.
The Playboy founder, whose passing marked the end of an era that was already winding down—and would actually come to a screeching halt just days later—as the tenets preached by the veritable man-bible were increasingly objected to, left a complicated legacy, as evidenced by the instant outpouring of appreciations laced with other, more pointed commentary about the man, the myth and the magazine.
Unlike some businessmen who leave their work at the office at the end of the day, Hefner embodied to an outrageous degree the Playboy lifestyle—a lifestyle that no dedicated subscription could help you acquire, but which served as the end-all and be-all image of maleness for so many of Hef's admirers.
Fully aware of the criticisms his publishing empire faced, namely that his magazine's very existence demeaned women and was setting the male-female power dynamic back 50 years (in many circles the mag never recovered from Gloria Steinem's damning 1963 exposé after she spent 11 days undercover as a Playboy Bunny), Hefner never relented from his position that Playboy, which launched in December 1953, was actually doing women a service by promoting female equality and women's rights and encouraging them to own and embrace their sexuality.
"The women's movement kind of came out of left field in the 1960s and 1970s when they turned on Playboy," Hefner told Esquire in 2013. "They were allies as far as I was concerned. How could they miss the point?"
Befitting his progressive outlook, Hefner also championed diversity, both in his magazine and in life, and was a deep-pocketed supporter of the civil rights movement and Jesse Jackson's Rainbow PUSH coalition. Through the years, Playboy included works by some of the great fiction writers and journalists, as well as interviews with the likes of Martin Luther King Jr., Miles Davis, Bette Davis (who famously said that she felt "abortion is better than having 10,000,000 children you can't support"), John Lennon and Yoko Ono, and Steve Jobs.
Not that Playboy didn't also have a less enlightened group of customers whose appreciation for the magazine was entirely prurient. There's a reason why the ol' Playboys-hidden-under-the-bed trope was a reality. But ultimately, Hugh Hefner was hardly the first idealistic visionary to create something that was more than the sum of its parts, but was also simultaneously misinterpreted or misappropriated by those who never saw nuance between those pages. Those who never, ever read Playboy—or maybe anything, for that matter—for the articles.
Yet even the most optimistic view of Playboy doesn't cancel out the fact that Hefner's unorthodox, glamorous lifestyle didn't have its downright weird, at times alarming, aspects. And yes, those aspects grew increasingly creepy-seeming the older he got and the younger his female companions got.
The twice-divorced publisher was 86 when on New Year's Eve in 2012 he married 26-year-old Crystal Harris, a model he first met in 2008 when she showed up for a Halloween party at the Playboy Mansion dressed in a French maid costume. There may have been intrigue at first sight, but Hef had his hands full at the time.
That was the year when both Holly Madison and Kendra Wilkinson—two of the three Girls Next Door Hef dated simultaneously between 2005 and 2009—moved out of the storied pleasure palace in Holmby Hills (which was sold for $100 million in 2016 with the understanding that Hefner could spend the rest of his life there). Madison, the first of the three to move out, and Bridget Marquardt, the last of the trio to go, had been around since 2001, when they were among seven women Hefner was dating and living with at the time.
When Madison left, sort of unbeknownst to Hefner ("Until a few days ago, we were still sharing the same bed," he said in an October 2008 interview), 19-year-old twins Karissa and Kristina Shannon had moved in—but they weren't dating the man of the house.
Meanwhile, Crystal was being celebrated as "Co-Ed of the Week" on Playboy.com in October 2008, and a year later the Arizona native was named Playboy's Playmate of the Month for December 2009, the big reveal as always taking place at Hefner's home/working-lifestyle space.
Soon enough Hefner started a relationship with Crystal and they announced in December 2010 that they were engaged to be married. Hef popped the question on Christmas Eve while they were opening presents, hiding the ring in a Little Mermaid music box, Ariel being Crystal's favorite Disney princess. The ring was initially too big, so it later had to be resized.
"I'm very surprised," Holly, who would later drop major bombshells about life with Hef in her 2015 book Down the Rabbit Hole, admitted to E! News after first hearing about her ex's engagement. "I have a lot of different feelings on it. I don't just feel one way. I kind of didn't want to put a generic statement out there, like, 'Congratulations!' because I felt everyone would see through that…I wanted to see him and Crystal and tell everybody face-to-face how I felt."
Questioning why water never seemed to stay under the bridge with this group, Crystal, who's celebrating her 35th birthday April 29, came down firmly on Kendra's side earlier this month in the latest flareup of the former Girl Next Door's sporadic war of words with Holly—who in her 2011 book she said she loved but who along with Bridget was more of a roommate than a close friend.
"I was at the mansion for a DECADE almost four years ago now and these ladies and their drama were there years before that," Crystal, who still goes by her married name on social media, wrote on Facebook April 9, after Holly said on the podcast Call Her Daddy that she and Bridget would always be close but she and Kendra had no relationship. Moreover, she talked about having "boring, basic sex" with Hefner and alleged that she had to sleep with him before being invited to move into the Playboy Mansion.
"I'm not trying to slut-shame anybody or anything but nobody ever got asked to move in unless they had slept with him," Holly added.
"Dude … it's 2021," Kendra wrote on Instagram in her apparent response. "Times have changed. I forgive and have kids to love and focus on." (As does Holly, two with ex-husband Pasquale Rotella.)
Crystal, who pre-pandemic had been travel blogging from enviable locales and has partnered with United Planet to lead a mindful excursion to Mexico City in May, continued in her reaction post, "So much time has passed. I side with Kendra here. Not sure why these women who shared an incredibly uncommon and rare experience (that will never be repeated in our lifetimes) can't get along? Maybe for the same reasons Holly and Bridget despise me for absolutely NO reason. I hope one day we can all get along and share experiences."
A couple weeks later, however, Crystal told Us Weekly that she understood at least why there might be lingering bad blood between Holly and Kendra (who didn't have much to say about Holly's jab but did tell Us that she and Crystal "will always be friends").
"I understand that Holly is probably finding healing by speaking about her experience, for sure," Hefner's widow explained. "I noticed because I'm trying to find my own healing as I reflect back. I know Holly went through some very hard things at the mansion. I think some of the things I went through are harder."
Crystal continued, "I can understand the contention between Holly and Kendra, especially because Kendra was kind of more checked out. And so, she had to deal with less, like, psychologically at the mansion. And I think that might be a source of bitterness with Holly." Moreover, Crystal understood Holly "because I was in the position that Holly was in. I became Hef's wife. I was with him all the time. I became just so invested in his life almost to the point of losing myself, so I can understand her perspective."
Hefner and Crystal revealed first to Piers Morgan on CNN that they had set a date for June 18, 2011, a Saturday, at the mansion. Hefner's brother, Keith, was going to be his best man and two youngest sons, Marston and Cooper, would be groomsmen, while the bride's best friend would be her maid of honor and her two sisters would be bridesmaids.
"He got married once in the front yard so I asked if we could do it in the backyard," Crystal joked.
Asked what she had to say to the skeptics who might be doubting the authenticity of their pending union, she said, "I love Hef. He's the nicest person I've ever met in my entire life. I have so much fun with him."
However, that first engagement didn't stick. Just days before they were to swap vows, she called it off.
Crystal tried to explain her cold feet to Ryan Seacrest on KIIS-FM a few days after the wedding was supposed to have taken place.
"For a while I've been having second thoughts about everything," she said. "I haven't really been at peace with myself lately. I didn't think it was really fair to him." Moreover, "multiple girls all around, it's not the lifestyle I wanted."
"I really don't know what happened," Hefner told Morgan. In a real Sex and the City movie-reminiscent twist, the July 2011 cover of Playboy, sent to print way ahead of time of course, featured Harris—a Hef-signature red silk robe slipping off her shoulders while she sported a sailor's cap and held a pipe—with the line "America's Princess. Introducing Mrs. Crystal Hefner." The cover ended up slapped with red stickers reading "Runaway Bride in this issue!" on newsstands.
"I think that in time, the rest of the story will play out, but..." Hefner paused. "I think the real problems began a couple of months before the wedding was set, when we were talking about"—Hefner cleared his throat—"when the lawyers got into it, when we were talking about the prenup and etcetera. And we went to London five or six weeks before and things did not seem quite the way they ought to be."
Leading up to their scheduled wedding day, "something was definitely not right, but I didn't see it coming," as far as Crystal walking out," he said. "I mean, I truly didn't see it coming."
Hefner agreed with Morgan that maybe he needed to get his head examined if he was seriously considering getting married for a third time, then at 85 to a 25-year-old woman. The father of four was previously married to Mildred Williams from 1949 until 1957, when he was getting his magazine off the ground, and then took a long bachelor break before marrying Kimberley Conrad, 36 years his junior, in 1989. They separated in 1998 and she moved next door to the Playboy Mansion with their young sons Cooper and Marston, but wouldn't divorce until 2010.
"I made the commitment, quite frankly, because I felt that I had, in a previous relationship with Holly, not been there for her in a way that she wanted me to be. I just wanted to do whatever would make the relationship work!" Hefner told Morgan. "You know, I was ready to settle down, it was about time." He smiled. "But on another level I must say, quite frankly, the following Monday, I woke up and I was single and I thought, this is the natural way of things. I ought to be single."
He explained that he had told Crystal that, if she was having doubts, he was fine calling off the wedding, but he was surprised to find her gone for good just as weekly Sunday Movie Night at the Playboy Mansion had gotten underway. She told him she had gone to stay with her mother in San Diego, but Hef was skeptical, having been unable to reach her there.
"I think an argument could be made that she took me for a ride," Hefner nodded. "But I must say, quite frankly, it was a pretty nice ride." Morgan laughed. "It was two and a half very good years and if she was faking it she did it very well."
Just a couple weeks later, however, Crystal sat down with Howard Stern and painted a less idyllic picture of what went on between them.
"I'm not turned on by Hef, sorry," she laughed after saying sex with the most famous playboy in the world lasted "like about two seconds." Moreover, she told Howard that they only had sex once during their relationship. She was, Crystal insisted, in love with Hefner when she accepted his proposal, but she just wasn't that physically attracted to him.
"Crystal lied about our relationship on Howard Stern but I don't know why. Maybe a new boyfriend?" Hefner tweeted in response to the interview.
Soon after, Crystal tweeted that she was "unprepared and blurted out things I shouldn't have said" on The Howard Stern Show. "I'm sorry." That October, she put her $90,000 diamond ring (which Hef had insisted she keep) up for auction at Christie's, where it sold for about half of its estimated value.
According to Esquire, Hefner told his male coterie of Movie Night pals, "If I ever try to get married again, shoot me."
However, he never bothered to take down a portrait of him with Crystal, painted by former Playmate Victoria Fuller, that had been hanging prominently in the mansion. There it still was in June 2012 when the two reconciled and revealed that their engagement was back on. Harris had a new dazzling ring on her finger.
They married on Dec. 31, 2012, in an intimate ceremony at the mansion, as if nothing untoward had happened.
"When the wedding didn't work out the first time, it was because of me," Crystal told Us Weekly afterward. "I needed to explore out there and take the time away. The time away really helped make me realize that where I'm meant to be is here with Hef. Our relationship is better than it ever has been before. I'm very happy and Hef's very happy and we're excited."
Perhaps the lawyer conversation wasn't so awkward the second time around.
In the end, Hefner and Harris were married for a little over four and a half years—and seemingly a contented four and a half years, although Hef's health was said to be in decline for some time. Crystal also revealed in March 2016 that she had been diagnosed with Lyme disease and had a "long road" to recovery ahead of her. That October, when rumors started circulating that Hefner was on his death bed, he tweeted a photo of the two of them settling in for movie night.
"Tonight's Mansion movie is the classic western, Shane," he wrote. He added, "I wish the tabloids had informed me a little earlier in the week that I'm sick. I would have cancelled my weekend plans."
Still, no matter what was happening behind the scenes, his passing still felt shocking when it actually happened, Hefner having managed to maintain an aura of agelessness—no matter how anachronistically—for so long.
After the funeral, Crystal told People, "I am heartbroken. I am still in disbelief...He was an American hero. A pioneer. A kind and humble soul who opened up his life and home to the world. I felt how much he loved me. I loved him so much. I am so grateful. He gave me life. He gave me direction. He taught me kindness. I will feel eternally grateful to have been by his side, holding his hand, and telling him how much I love him. He changed my life, he saved my life. He made me feel loved every single day."
Hefner's net worth when he died was estimated to be as much as $110 million, including his 100 percent ownership of the magazine and 35 percent of the Playboy brand. Crystal was reportedly not included in his will but provided for in their prenuptial agreement. The summer before he died, Hef also purchased a 5,900-square-foot house in the Hollywood Hills for $5 million, putting it in Crystal's mother's name.
"He believes in love," Crystal told Esquire in 2013. "Hef loves me more than anybody else in a relationship ever has. It took me time away to realize that. I think I realized that here is where I'm meant to be."
"All our friends think it's made in heaven," Hefner added. "It's only people who don't know us, who simply see us as stereotypes in terms of age and beauty… I just feel very, very fortunate to have found her at this stage in my life. I saved the best till last."
(Originally published Sept. 28, 2017, at 2:33 p.m. PT)