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.

But the infamous residence's owner, Hugh Hefner, who died yesterday at the age of 91, wasn't exactly aiming for ordinary.

The Playboy founder, whose passing marks the true end of an era that was already winding down as the tenets preached by the veritable man-bible were increasingly objected to, leaves a complicated legacy behind—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.

Hugh Hefner

Bettmann Archives / Getty Images

"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 greatest fiction writers and journalists of all time, 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.

1993 Playboy Cover, Anna Nicole Smith


Yet even the most optimistic view of Playboy doesn't cancel out the fact that Hefner's unorthodox, glamorous lifestyle didn't have its creepy and downright weird 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, 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.

2008 was the year when both Holly Madison and Kendra Wilkinson—two of the three Girls Next Door Hef dated simultaneously between 2005 and 2009moved out of the mansion. 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. 

Hugh Hefner, Holly Madison, Kendra Wilkinson, Bridget Marquardt

Elayne Lodge/Playboy Enterprises

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.

Eventually Hefner started a relationship with Harris 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—Harris' favorite Disney princess—music box. The ring was initially too big, but they figured it out.

"I'm very surprised," Holly Madison, who would later drop major bombshells about life with Hef in her book Down the Rabbit Holeadmitted 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."

Hefner and Harris 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 Harris' 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," Harris 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, Harris called it off.

She 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 Piers 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 on the cover, partially clad in Hef's smoking jacket, 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 wedding day, "something was definitely not right, but I didn't see it coming," as far as Crystal walking out. "I mean, I truly didn't see it coming."

Crystal Harris, Hugh Hefner

Charley Gallay/Getty Images for Playboy

Hefner agreed with Morgan that maybe he needed to get his head examined if he was seriously considering getting married again, then at 85 to a 25-year-old woman.

"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! 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 Harris that, if she was having doubts, he was fine calling off the wedding, but he was surprised to find her gone for good after she had wandered off 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, not having been able 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, Harris 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 Stern that they only had sex once during their relationship. She was, Harris 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, Harris tweeted that she was "unprepared and blurted out things I shouldn't have said" during that interview. "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.

Crystal Harris, Hugh Hefner, Wedding Dress


According to Esquire, Hefner told his male coterie of Movie Night pals, "If I ever try to get married again, shoot me."

Meanwhile, Hefner 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 Playboy Mansion.

"When the wedding didn't work out the first time, it was because of me," Harris told Us Weekly afterward. "I needed to explore out there and take the time away [from Hef and the Mansion]. 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.

Hefner's net worth when he died is being estimated at as much as $110 million, including his 100 percent ownership of the magazine and 35 percent of the Playboy brand. In addition to Harris, he's survived by four adult children, and reportedly the prenuptial agreement provides for his widow but she is not included in his will.

The Playboy Mansion was sold last year for $100 million, with one of the terms of sale being that Hefner would continue to live there for the rest of his life. Earlier this summer he purchased a 5,900-square-foot house in the Hollywood Hills for $5 million, putting it in Harris' mother's name.

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. Harris also revealed in March 2016 that she had been diagnosed with Lyme disease and had a "long road" to recovery ahead of her. Last October, when rumors started circulating that Hefner was on his death bed, he tweeted a photo of him and his wife 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."

"He believes in love," Harris 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."

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