What Was Living In The Playboy Mansion Really Like?

Hugh Hefner was "nothing if not a genius at reading the signs of the times" said Alex Witchel in his 1992 piece on the Playboy mogul for The New York Times. At the time of Hefner's death in 2017, he had a net worth of $50 million, according to Celebrity Net Worth. The business itself was even more potent. At its peak, the Playboy magazine had a world wide circulation of 5 million copies per issue and the company was valued at $207 million in 2011, per a later publication by The New York Times. Based on success and financial capital, yes, Hefner was a genius.

Celebrities from Anna Nicole Smith to Jenny McCarthy launched careers thanks to the exposure they received from Playboy. For others, like Pamela Anderson, the magazine only amplified their already-budding careers. So to be fair, it wasn't just Hefner who grew rich from the world of Bunnies.

And the Playboy Mansion itself became an iconic symbol of the sexual revolution in America and an extension of Hefner's genius. In NYT's 1992 feature about Hef, Witchel said that access to the mansion was "as carefully controlled as all other aspects of Mr. Hefner's life." Not only was the mansion controlled, it was pitched as an Eden. It boasted "English countryside" aesthetics, had a zoo, and a grotto. While it looked like a fairytale from the outside, life inside the Playboy Mansion could be the exact opposite.

The first-ever Playboy Mansion was actually in Chicago but in 1971, Hugh Hefner decided to relocate Playboy to California. He opted for a 5.3 acre estate in Los Angeles with the Gothic Tudor mansion already in place, as Architectural Digest notes. The mansion was built in 1927 for real estate and department store magnate Arthur Letts Jr.

Hefner paid $1.1 million for the property which was, as Fancy Pants Homes notes, a record sale in Los Angeles at the time — and the impressive price tag came with an impressive property. The mansion boasts nearly 22,000 square feet and holds a jaw-dropping 29 rooms, including "a wine cellar that can be accessed through a secret Prohibition Era door," Architectural Digest adds. But Hefner wasn't only about parties. The mansion held four offices because you don't buy the most expensive house in Los Angeles without getting some work done.

The outdoor space was perhaps even more impressive. There was a wishing well on the grounds, as well as basketball courts and of course, the legendary grotto. While it's essentially a swimming pool, it's really so much more. As Fancy Pants Homes points out, there's a waterfall, a barbecue area, a sauna, and a koi pond. No wonder it became the centerpiece of the mansion's parties. Adding to the mansion's epic proportions, the location is one of the "few private residences in Los Angeles with a zoo license," AD explains, and according to Fancy Pants Homes, the property had a license for year-round fireworks.

While the Playboy Mansion certainly looked like a dream, being a live-in girlfriend was a totally different story from being a guest. As The Mirror recounted, Hugh Hefner supposedly insisted that his girlfriends have blonde hair and would reprimand them if they were spotted in public looking disheveled or tipsy, and they were not allowed to speak when Hefner was "being interviewed at the mansion." The one area in which Hef's girlfriends had free rein was with plastic surgery; the emperor of Playboy let them get as much of it as they wanted.

Holly Madison, a long-time girlfriend of Hefner's, gave the dirt to GQ on other rules and expectations when living at the mansion. His girlfriends were supposed to be monogamous with him, but only because outside relationships might ruin the Playboy brand. (Though many girlfriends allegedly broke this rule.)

Per GQ, there was also a weekly schedule at the mansion that included "Family Night," "Club Night" and "Fun in the Sun" day. By all accounts, they really stuck to the itinerary, and it sounds pretty intensely scheduled for a "fun" lifestyle. "Groundhog Day"? More like Bunny Week. 

This might not be one of the first things to come to mind when discussing the Playboy Mansion, but there has been much discussion about the food of the estate. William S. Bloxsom-Carter, who worked as the mansion's chef, spoke to Haute Living about what it was like to cook at the storied abode. Carter shared that Hef would have "half a grapefruit every day" and liked "fried chicken with mashed potatoes, which is his mother's recipe." But Hefner wasn't the only one living at the mansion, and he wasn't the only resident who enjoyed food made in the mansion's kitchen. "We do cook for the Playmates," Carter went on. "We want them to feel relaxed and at home, as if they were in their own kitchen. That's very important to Mr. Hefner."Food prep at the mansion was a major operation. There was 24-hour service for the residents, Gourmet notes, and the annual budget got up to $1.2 million. 

Longtime Playmate Kendra Wilkinson spoke candidly in her 2011 memoir "Sliding into Home" about how she used food as an escape while she was living in the manse. "I was disappointed in myself," she wrote (via People). "I had this whole mansion and a great life to enjoy, and all I was doing was lying around and eating. I felt so lazy and miserable. This was supposed to be paradise, but for me, it wasn't."

While the Playboy Mansion sounded pristine in its early days, rumor has it that it was dirty and poorly cared for. In her 2006 tell-all memoir, "Bunny Tales: Behind Closed Doors at the Playboy Mansion," Hugh Hefner's ex-girlfriend Izabella St. James got into many of the reasons why she believes the abode was "not the highly glamorous place people imagine it to be." She described the white carpet as being "gray and stained" and the mattresses being "worn out and stained." What's more, evidently there was no shortage of dog droppings throughout the home. As Holly Madison shared in "Down the Rabbit Hole" (via New York Post), the pooches of the Playboy Mansion apparently let it rip all over the interior of the house. St James noted Madison eventually persuaded Hef to swap out the dingy flooring with a darker carpet, but they went with a "dark blue with different colored patterns, which made poop-spotting much more difficult." Well okay, then.

Former Playmate Jenny McCarthy also spoke about the deterioration of the Playboy Mansion on "Watch What Happens Live." "When I was a Playmate, it was like a library," she said. "But now, when I go there ... it's an orgy." She described the environment as being "not sexy," adding, "It's, like, David Hasselhoff with an 18-year-old. ... It's gross." Yikes.

Being a newcomer at the Playboy Mansion apparently meant being hit with expectations. Reportedly, when the established girlfriends got tired of sleeping with Hugh Hefner, they would put pressure on the newcomers to take over. Zoe Paul, an ex-girlfriend of Hefner's, told The Sun that she acted as a "scout" for new women. Hoping to become famous through the magazine, many of the young women apparently obliged.

"Before we got in the limo I'd tell them what was about to go down," Paul recounted. "I would say, 'Listen, once we get back it's going to get wild and you will have to have sex with Hef and do things to get his attention, or he will lose interest in you.'" Part of Paul's motivation was to stay in Hefner's good graces by bringing in new women. "When I brought new girls back we'd see a big change in Hef," she said. "He'd become like the playboy he was in his younger years." Yet, as Paul told The Sun, things could get dark. "If they refused sex or were resistant, he'd get angry and take it out on us," she said.

Holly Madison echoed this in her memoir "Down the Rabbit Hole" (via People), saying that some of Hefner's girlfriends were "eager to bring as many girls up into the bedroom as possible," so that Hef would be "less likely" to sleep with them.

If anyone was wondering what it was actually like to sleep with Hugh Hefner, look no further. Several of his ex-girlfriends have dished on the experience which, frankly, doesn't sound great. Holly Madison explained a typical night in her memoir "Down the Rabbit Hole" (via GQ). "Two huge television screens projecting graphic porn lit up the otherwise dark bedroom," she said. "In the middle, a very pale man was tending to his own business...The girlfriends, in various stages of undress, were sitting in a semi-circle at the edge of the bed."

Zoe Paul gave a similar account to The Sun. "Hef would normally pass around a joint we'd all smoke," she said. "He also took Quaaludes and Viagra. I don't know how many. Then we would take turns." Paul described the incredibly mechanical way she went about sleeping with Hefner. "When it was my go on top I'd count two minutes in my head as that's how long it would take before he moved to the next girl." Paul also alleged Hefner would not use protection. "I was worried about getting STDs," she told The Sun. "After the orgies we'd always go to the doctors to get tested."

When the Daily Beast asked him about the aforementioned health concerns, Hefner implied that protection was in fact not used but did say he "was very careful and very concerned about taking care of everybody in terms of sexually transmitted disease." He also told the outlet that testing was a part of the routine.

Holly Madison, Kendra Wilkinson, and Bridget Marquardt became household names thanks to the hit reality show "The Girls Next Door." As Madison noted on MySpace (via People), the cash was apparently good: "I never cared about the salary when I got the job [at Playboy] — I made my money doing 'Girls Next Door,' and I just did the job because I loved it." However, it wasn't always good, as the trio apparently didn't see a cent for the first season. According to "Down the Rabbit Hole" (via GQ), when Wilkinson once asked for financial compensation, she was told by a producer: "You. Are. Replaceable... This is not a show about the girls, it's about Hugh Hefner.'" Ah yes, because everyone was tuning in to watch him walk around the Playboy Mansion in his housecoat. 

"We were constantly reminded that the show was Hef's show — our contributions were irrelevant," Madison wrote (via People). "We were the decorative icing, not the cake. According to our boyfriend, he could have splashed any three blondes on-screen and found instant success." 

Hefner had a different take. In his 1992 interview with The New York Times, he looked back on his oeuvre and said, "Playboy has become a wonderful rite of passage. Its message for children is that sex is good. The idea of women as playthings is someone else's political agenda. It is not my view or anyone's at the magazine." Sure, that might be his take, but the ex-girlfriends seemed to share different memories.

Izabella St. James, a former girlfriend of Hugh Hefner, wrote about the process of collecting a weekly allowance. From a safe in his bedroom, Hefner would hand out the amount in $100 bills but use the opportunity to correct each woman, she claimed in her memoir "Bunny Tales: Behind Closed Doors at the Playboy Mansion." "Most of the complaints were about the lack of harmony among the girlfriends — or your lack of sexual participation in the 'parties' he held in his bedroom," St. James wrote. "If we'd been out of town for any reason and missed one of the official 'going out' nights [...] he wouldn't want to give us the allowance. He used it as a weapon." St. James noted too that all of the girlfriends hated this part of the week.

After St. James published her memoir in 2006, Hefner took the opportunity to respond to her claims that he used money as a manipulative tactic with his girlfriends. Speaking with the Daily Beast in 2011, he confirmed that he indeed did dole out cash. "That part is true," he began. "If you write it and make it sound sleazy, that's easy to do. But the girls got a clothing allowance."

But St. James wasn't alone in her distaste for the procedure. Kendra Wilkinson told Us Weekly (via The Independent), "I hate putting my hand out, but we couldn't have jobs other than getting appearance fees." While Hefner tried to defend himself, his ex-girlfriends evidently didn't see it as innocuous.

A major theme that continuously comes up when talking about the real story of the Playboy Mansion was the alleged rampant drug and alcohol use. 

Zoe Paul spoke with The Sun and claimed that Quaaludes were a favorite at the mansion. The pills, according to PBS, act as a "sedative and hypnotic." Paul explained, "Hef always carried about ten Quaaludes and handed them out to his girlfriends." Paul, said she'd act as a recruiter for Hugh Hefner, added: "I kept spares so I could give them to the women I met. I'd stopped taking them as they made me feel sick. But I'd tell the girls, 'We all take them you should too.'" In "Bunny Tales," Izabella St. James offered a similar account: "In the limo, Hef would also hand out Quaaludes to whichever Girlfriends wanted them." In a 2011 interview with the Daily Beast, Hefner denied all of this. "If she was taking Quaaludes, she was taking them on her own. I wasn't supplying drugs to the girls," he said.

In "Down the Rabbit Hole" (via People), Holly Madison said that "[t]he climate inside the mansion was toxic," noting "cocaine benders" as common, but something she chose to opt out of. But Kendra Wilkinson shared her own experience on this subject in her memoir "Sliding into Home." "I had to be very drunk or smoke lots of weed to survive those nights — there was no way around it," she wrote. Certainly not a PG experience.

Many former girlfriends of Hugh Hefner claim that while there was copious amounts of sex at the Playboy Mansion, intimacy was in scarce supply. This might not come as a huge shock, looking back at Hefner's chronicled story in 1992 by The New York Times. The article claimed that Hefner's mantra was "if sex with emotional involvement is best, sex without emotional involvement is better than none at all."

Holly Madison reiterated this in "Down the Rabbit Hole" when she described nights with Hefner and all his girlfriends. "There was zero intimacy involved. No kissing, nothing," she said, (via People). Madison also got a little more explicit about the intimate experience itself: "It was so brief that I can't even recall what it felt like beyond having a heavy body on top of mine." Madison added that Hefner "finished off by himself" (via GQ).

Interestingly, Kendra Wilkinson had a different take on Hefner outside of the bedroom. In her memoir "Sliding into Home," she gave a more positive description of her relationship with him. "Staring into his eyes, I didn't see a man four times my age with ten times more girlfriends than most," she wrote. "Even though I hardly knew him yet, I saw a sweet man who made me feel really good about myself — a true gentleman. It was weird, but in my heart, I felt like he was someone I could possibly trust." 

Many of Hugh Hefner's ex-girlfriends have said that the Playboy magnate was incredibly critical, determined to make sure their appearance lined up with the Playboy brand. There was an expectation on Hefner's part that the girls in the mansion look perfect and he paid for all the plastic surgery they wanted. As Izabella St. James shared in "Bunny Tales," the two favorite procedures were nose jobs and breast augmentation. "Six out of seven girls at the Mansion had their noses surgically altered," she wrote.

Hefner was keen to foot the bill, but according to one of exes, he was also keen to comment on appearance. In "Sliding into Home" (via People), Kendra Wilkinson remembered that after telling Hef she felt insecure about her weight, he replied, "Well, you look a little bigger. 'Maybe you can go to the gym.'" And "Down the Rabbit Hole" (via People), Holly Madison revisited some of the moments when he put her down. Once, she wore red lipstick, and apparently, he was not a fan. "'Don't ever wear red lipstick again,' [Hefner] warned me in a low voice and turned toward the door. Deciding he hadn't done enough damage, he served me one final blow before storming out of the room: 'You look old, hard and cheap.'" Madison went on to add, "I'd invested every part of myself in the mansion... I felt so trapped and so vulnerable to his criticisms." No wonder she spoke out once she was out of there.

While the gates at the Playboy Mansion were necessary to ward off the uninvited, some of the residents did not always feel a sense of protection.  "Everyone thinks that the infamous metal gate was meant to keep people out. But I grew to feel it was meant to lock me in," Holly Madison wrote in "Down the Rabbit Hole." "I wasn't quite sure how I ended up in this curious, often dark world." For Izabella St. James, the mansion wasn't so much a trap as an unrealistic fantasy. "Living at the Playboy Mansion is like living in an unrealistic bubble where everyone is beautiful," she shared in "Bunny Tales." "When I left the Mansion I could not help but notice how 'normal' and ordinary most people looked... Then I realized that it was the Girlfriends who looked like cartoon characters, too perfect and too exaggerated. I needed a reality check."

In "Sliding Into Home," Kendra Wilkinson talked about the 9 p.m. curfew. "I'd get a text message from a girl that read, 'Having so much fun in Vegas. Wish you were here! Partying with all these football players.'" she wrote. "I felt so trapped and angry when I was missing out on something good." 

When the Daily Beast asked Hef about the mansion's curfew, he said, "That was also true—and widely publicized. It wasn't a big secret." He also shared his reason for the mandate: "So they wouldn't be running around on me!"

For anyone who has watched footage of the Playboy Mansion, especially the reality show "The Girls Next Door," Holly Madison, Kendra Wilkinson, and Bridget Marquardt looked like best friends. But behind the scenes, it was completely different.

Wilkinson noted in her memoir "Sliding into Home" that things got really competitive. "During that first season, Bridget, Holly, and I continued to keep our distance, except when we were filming. We did our thing off camera, and there was an unspoken competition for camera time when the cameras were around," she wrote. "Each of us wanted the others to look good and be successful, but whether they will admit it or not, I think we each wanted the spotlight and to look the best in every episode."

Zoe Paul moved to the Playboy Mansion in 2000, so while she was an earlier girlfriend than the three above, she was no stranger to conflict. "There was a lot of competition between his seven girlfriends. We all wanted to make sure we were the one he'd spoil the most," she told The Sun. Madison also dished on the animosity within the mansion on the podcast "Call Her Daddy" in April 2021. "Imagine having sex with somebody in a room full of women who all hate you and you know they're all talking s*** about you. Like, how horrible? It was gross," Madison said. So it was nothing like the best friend slumber party that the reality TV show painted it to be.

This dark side to the Playboy Mansion is ages old and frankly, at this point, we're not surprised. Tell-alls have been leaking out of Hugh Hefner's world for years. Gloria Steinem broke the gates open in 1963 when she surreptitiously worked at the New York Playboy Club as a Bunny to publish "A Bunny's Tale." While certainly a lure for the prurient, the reporting covered Steinem's 17-day experience working in the Playboy world.

Steinem's big takeaway was that while the Playboy universe is pitched as a way for women to succeed, that was not the case. "We get tips, but the Club takes 50 percent of the first $30 worth of those that are charged, 25 percent of amounts up to $60 and 5 percent after that," she wrote. "'That means half of everything,' whispered a girl in costume. 'Who gets more than $30 a day?'" 

Hefner had a different take on all of this. "I'm a decent human being," he told the Daily Beast. "And I treat women very well. I take pride in that." That's his side of the story. Many of his ex-girlfriends, however, have released tell-all memoirs that paint a very different picture. Their accounts are not always about Hefner but one thing is for sure: life in the Playboy Mansion was no Garden of Eden.