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    Hugh Hefner’s Widow Names Jack Nicholson & More Playboy Mansion Guests

    soreceryBy No Comments12 Mins Read

    Watch: Hugh Hefner’s Widow Crystal Harris Asks Jessica Biel to Back Out of Playboy Movie Role

    Crystal Harris witnessed some less-than-model behavior during her years at thePlayboy Mansion. 

    Hugh Hefner’s widow revealed a few of the regular celebrities who would frequent the mansion, admitting that there were some “really horrific, horrible men” who came through the gates of the famed estate.

    “It was tough,” Harris toldPage Six in an interview published Oct. 29. “Hef surrounded himself by like-minded men, Bill Cosby included, DonaldTrump included, and it was very sad.”

    The 40-year-old—who was married to Hefner from 2012 until his death in 2017 at the age of 91—said Cosby was a regular and hosted the Playboy Jazz Festival “for many, many years,” adding it was “awkward” to take photos with him.

    Harris also referred to the Playboy Mansion as “JackNicholson’s drive-thru.”

    “He could drive up, there’d be women there, there’d be food there, and he would just collect what he needed and left,” Harris alleged of the Oscar winner. “We all know that that man is also notorious for being a regular, very regular at the mansion.”

    read

    The Dark Side of Crystal Harris’ Marriage to Hugh Hefner

    The After the Mansion podcast host also called out comedian JonLovitz, noting he was “part of the problem.”

    “I think many men who came up to that mansion,” she explained, “[and] were very sexist and misogynistic are all part of that problem.” 

    Luckily, Harris did have several positive interactions with celebrities, like comedian George Lopez, who took over the Playboy Jazz Festival from Cosby in 2013. 

    Denise Truscello/WireImage

    “George Lopez was always very, very, very nice,” Harris said. “He never came to the mansion.”

    She had also had fond memories of Star Wars actor MarkHamill and his wife MarilouYork, saying the couple would be at the mansion “every once a while” and “they were lovely.”

    “Some of the good guys were mostly the women,” she mused. “A lot of the women that came by were good, good celebrities.”

    In particular she recalled actress JulieNewmar—best known for playing Catwoman on the 1960s Batman TV series—as being “wonderful.”

    E! News has reached out to reps for Cosby, Nicholson, Lovitz, Lopez and Hamill for comment but has not heard back, while a rep for Newmar had no comment when contacted by E! News.

    Charley Gallay/Getty Images for Playboy

    Over the years, Harris has been candid about the difficulties she faced at the Playboy Mansion, as well as in her relationship with Hefner. 

    “It was emotionally abusive,”Harris told E! News of her marriage in 2024. “It was very restrictive. I didn’t realize how bad it was until I was away from it for a while.”

    “When I was at the mansion, I didn’t know who I was,” she added. “When you don’t know who you are, that could be dictated to you by somebody else and if that’s given to you by someone else, it could also be taken away. So, it’s very important for you to have your own power.”

    For a look at more revelations about Harris’ life in the Playboy Mansion that she shared in her memoir Only Say Good Things: Surviving Playboy and Finding Myself, keep reading.

    Photo by Denise Truscello/WireImage

    Life at the Playboy Mansion Was a Constant CompetitionThough portrayed as a spot to indulge your wildest fantasies, life in the famed Playboy Mansion was quite restrictive for Crystal Hefner (née Harris), who was just 21 when she met and subsequently moved in with magnate Hugh Hefner in 2008.Her curfew, for instance, was 6 p.m. on the dot. “The pantry staff would start frantically calling my phone at exactly 6:01 p.m.,” she writes in Only Say Good Things: Surviving Playboy and Finding Myself. “And then I would run in, pushing through the heavy wooden door, and go find Hef, so I could kiss him on the cheek and show him: Here I am, I’m home, I’ve followed the rules.”There was also little opportunity for privacy. “Hef, of course, held the master key that ensured no one could ever lock him out.” But the toughest bit for the psychology major who shared Hef with twins Karissa and Kristina Shannon, among other girlfriends, was the feeling she was constantly being compared to a parade of other women. “Playing the role of someone else’s image of you every day and night is exhausting—physically, mentally, and in a way that feels like your soul is actually tired,” she writes, “like some kind of life energy battery is running low.”

    Denise Truscello/WireImage

    Crystal’s Sex Life With Hugh Hefner Was Not GreatLet’s talk about sex—because Crystal insists it was never the best with the mogul who was six decades her senior. From the first night they met at his 2008 Halloween party, the entire bedtime ritual was “odd and robotic” she writes of the process that she says included bringing in new women from the party, changing into the requisite silk pajamas, dimming the lights, turning on the music and porn and passing around marijuana. With Hef not even looking at her, but rather the mirror placed strategically above the bed, “He seemed less sex-savvy than some of the teenage boys I’d been with years ago,” she reveals. ”It was clear to me Hef had never taken a moment in his entire life to figure out how to please someone else.”

    Michael Caulfield/WireImage

    Gaining Weight, Condoms and Talk of Death Were All Off-LimitsWith everything from grilled cheese to filet mignon at her disposal, “I quickly gained a few pounds without realizing it, like a first-year student putting on the ‘freshman fifteen,'” Crystal shares. At 134 pounds, she didn’t really notice, “but Hef certainly did. One night when the twins and I were undressing for him, he gave my body a critical look and raised his eyebrows. ‘Looks like somebody needs to tone up,’ he said lightly, but with a warning note in his voice. He gave my hips a light tap, to call my attention to the offending area.” In a panic, she hit the gym and began limiting her food: “I dropped those offending extra pounds fast.”She “obediently” began following other what she called other unwritten rules as well, alleging she was not allowed to ask Hef to wear a condom (“If anybody caught something, he had a personal doctor on staff to treat us”), talk about death or “anything unless it related to Hef.” As a result, she writes, she “jumped rank” and was moved into the primary bedroom as Girlfriend No. 1. While Hef passed away in 2017, his son Cooper Hefner defended his legacy after the 2022 release of A&E’s Secrets of Playboy, tweeting that his father “was generous in nature and cared deeply for people. These salacious stories are a case study of regret becoming revenge.”  

    David Livingston/Getty Images

    Crystal Received an Allowance From HefTo afford essentials like gas, clothes and the beauty items required to maintain her flawless appearance, she relied on her weekly $1,000 allowance they received every Friday morning.”It was demoralizing on purpose,” she opines. “It was infantile. But since we couldn’t work outside the house, it was our only source of income.” 

    Brian To/FilmMagic

    Hef Maintained a Little Black BookThe Playboy publisher “could be charming, and he could be cruel,” Crystal writes of his “mercurial” mood swings. “He could make you feel like you were the most important person in the entire world one minute, and like you were less important to him than the rugs that he walked across.”And he was fastidious when it came to taking notes. Along with photos he collected of his various girlfriends flashing the camera—”Rolls and rolls of potential blackmail, if he ever wanted to use it that way”—Hef kept a little black book “where he wrote down the names of every single women who went up to the bedroom,” reveals Crystal.His conquests included celebrities, politicians and business leaders, she alleges: “He only told me one specific name, a famous television host still on the air, a sweetheart in America but a victim in the mansion.” 

    Denise Truscello/WireImage

    Hef Developed an Addiction to OpiatesOriginally starting as a way to treat his back pain, “Hef’s addiction to pills was a well-known secret in the house,” claims Crystal, “and one nobody every talked about.” In addition to the Quaaludes he reportedly offered to his women, “doctors had no problem prescribing him opiates,” Crystal writes of Hef. “His doctor had given him an ‘earthquake supply’ of Percocet. We didn’t know until much later just how much he had tapped into that earthquake supply in addition to his regular monthly refills.” 

    Charley Gallay/Getty Images for Playboy

    Crystal and Hef Never Discussed Marriage Before His Grand ProposalWhen Hef asked Crystal if he fully wanted to be part of his world on Christmas Eve 2010, proposing with a Little Mermaid-themed music box and a diamond, she was stunned. “As far as romantic proposals go, it wasn’t,” she confesses of the moment, captured by cameras for an already-planned Marrying Hef special. “We hadn’t even talked about marriage, we weren’t in love, and I was confused.” Though she slipped the ring on as expected and began filming the wedding planning process, her doubts grew. The breaking point: Learning her payday for the special would be a paltry $2,500. “In that moment, I snapped,” she writes. “I realized that Playboy was going to squeeze everything they could out of me for as long as I stayed here.” So she left. Running toward the gate, she heard Hef’s voice over the mansion loudspeaker. “‘Close the back gate!’ he boomed. ‘If Crystal tries to leave, detain her!'” Feeling trapped, she continues, “I turned around and walked, steadily, back to the house.” 

    Tibrina Hobson/Getty Images

    Crystal Carefully Plotted Her EscapeRealizing she “had to make a plan,” Crystal began squirreling away her allowance money and doing paid promotions on social media. Making an appearance as a Playmate at a Lil Jon performance, she decided she would learn how to DJ “so that I was more than just an accessory.” A producer pal connected her with Jordan McGraw and while mansion staffers began planning her wedding to Hef, Crystal found herself forming a connection with the musician. “He made me feel special, just for being me,” she explains, “and the contrast between that and who I was in the mansion made me giddy.” Buoyed by support from Jordan and his dad Dr. Phil McGraw, Crystal slowly began moving her stuff out of the mansion and into the closet Jordan had cleared out for her.And in June 2010—just days before the planned nuptials—she left in the middle of movie night, she left, telling security guards she was just running out to get tampons. “I didn’t feel guilty for sneaking away,” she admits. “I didn’t feel guilty about the wedding. Hef had never asked me to marry him. Going along because there’s no choice and saying ‘yes’ are two very different things.” 

    Photo by Vivien Killilea/Getty Images for Smile Train

    Crystal Had Several Conditions for Returning to HefPainted a runaway bride in the media, “I ran straight to Jordan and hid from it all,” she writes. “When Jordan kissed me for the first time, I felt butterflies.” But the giddiness proved to be temporary. While she writes “I wanted so badly for it to work out,” she realized she was making the same mistakes: “I ran from one man to another, hoping it would fix all my problems.” Devastated by her split from Jordan and with no job and a dwindling bank account, “I felt unprotected and vulnerable, so in my head I began to rewrite history,” Crystal shares. “Life at the mansion hadn’t been so bad. They had never really aggressively prevented me from leaving. I had it pretty good there.” So when Hef’s longtime secretary Mary O’Connor called explaining how much he missed Crystal, “I felt myself softening more quickly than I would have liked.”Though she agreed to return, she had some demands: While sex could remain a group activity, she “cleaned out the other girlfriends.” As she puts it, “The mansion was still a twisted underworld. But at least now, I felt a little bit in control.” 

    Dan Tuffs/Getty Images

    Crystal Wasn’t By Hef’s Side When He DiedWhen she and Hef finally did marry on New Year’s Eve 2012, Crystal wore pink, writing, “I told myself that when I got married for real someday, I would wear a white dress.” Playing Hef’s wife was still a job, she confesses, “but it felt like a promotion.” Still, it was work. In addition to kicking off a DJ and real estate career, growing her social media platform and studying crypto currency, Crystal found herself adopting the role of caretaker.”I was there at his elbow holding his arm to support him so when we were out in public, nobody would know he was starting to get frail or confused,” she writes. “I wasn’t going to let him down.” Though she faced her own health battles—Lyme disease, breast implant illness and toxic mold exposure—she became “hyper-vigilant about protecting his image.” When she returned from a week away in late 2017, Crystal learned that Hef had developed a UTI with “a strain of E. coli that was considered a ‘super bug.'” Though they turned his bedroom into a makeshift hospital room complete with the necessary antibiotics, he began to slip in and out of consciousness.While out in the hallway debating the next steps, recalls Crystal, “one of the nurses came out of the bedroom and said simply, quietly, ‘He’s gone.'”

    Instagram / Crystal Hefner

    Crystal Never Really Loved HughReflecting on how Hef made an effort to see she would be taken care of—setting aside his Playboy retirement fund and buying a house for her as the mansion itself had already been sold—Crystal speculates, “maybe he really loved me in some small way.” As for her feelings toward the nonagenerian, “Yes, I loved him, but I loved him the way someone might love their kidnapper after 10 years of being with them every day,” she writes. “I feel sorry for him, that he didn’t know how to love, how to actually see another person, or how to really connect in a meaningful way. The man thought to be the greatest lover in the world never knew how to love at all.” 

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