Inside The Playboy Mansion & Its Infamous House Parties

Monica Gray - May 25, 2023

Photo: CBS News.

Step into the world of legendary debauchery at the Playboy Mansion in Los Angeles. This notorious pleasure palace, located at 10236 Charing Cross Road, has become an icon of wild nights and scandalous mornings. Imagining the chaos that unfolded within those walls is mind-boggling. From the daytime rowdiness to the electrifying nights when celebrities graced the towering doorways, the Playboy Mansion was a realm of strange debauchery. We can only read about the legendary parties hosted by Hugh Hefner and his bunnies, as the experiences were reserved for a select few.

The Playboy Mansion boasted an 80-person staff, a sprawling estate with luxurious amenities like outdoor aquatics, a 24-hour gourmet kitchen, a private gym, secret doors, a wine cellar, a game house, a home theater, and even exotic animals roaming the grounds. These parties were not for the faint of heart, featuring spectacles straight out of a movie, such as Burlesque dancer Dita Von Teese enchantingly performing in a giant martini glass, adorned with nothing but a smile and earrings. The Playboy Mansion’s allure was further heightened by the attendance of numerous celebrities, and it remained the sole residence in Los Angeles with a zoo license. While Hugh Hefner may have passed away in 2017, the legacy of his parties will forever live on. If there’s one experience in life we yearn for, it’s a chance to revel in the extravagance of a Playboy mansion party.

From Mellow To Wild

With trays of party favors and beyond, there was nothing like a Playboy party. Ex-Playboy bunny Jenna Bentley said, “There will never be anything the same as his parties. I mean, people think they were wild but they were wilder than you can imagine.” Barbie Benton, one of Hefner’s ex-girlfriends, said the parties ranged from mellow and relaxed, to wild and rowdy. While the wild nights were fun, regarding the more mellow movie nights, she said, “Everybody always got a free dinner and many people would just come for a meal and movie — Friday night was always movie night. Hef would never charge anyone.” That sounds more like a Playboy party we could handle (People).

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Donald Trump Made An Appearance At Several Parties

It wouldn’t be a historic Playboy party without Donald Trump. In 1993, Trump attended the 40th celebration of Playboy at the mansion. He conducted interviews and snapped photos of models on Polaroid cameras. And if you’ve ever seen Centerfolds, the soft-core porn film Trump starred in where he pours a bottle of champagne into a limo. Former Playboy bunny Pauly Shore said, “He was just there, just hanging like Bill Maher. It was some Easter egg night or day, and he was in a suit and talking to girls.” There are some people we wouldn’t want to see at any party, let alone a Playboy party, and it’s Donald Trump (People).

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The Nights Got Rowdy In The Famed Grotto

The Playboy Mansion parties involved beautiful women and a lot of sensuality. Hefner usually oversaw the ordeal wearing slippers and a robe. But in reality, there was a strange mix of celebrities, as we’ve seen with Trump’s appearance. Guests mingled with exotic animals like monkeys, llamas, and flamingoes. But nothing was more gaudy than nights at the famed cave, where things were more gross than sexy. Former Playmate Playboy bunny Jenny McCarthy said, “When I was a Playmate, it was like a library. It was strict. But now when I go there — or a few years ago — it’s an orgy. But it’s not sexy. It’s, like, David Hasselhoff with an 18-year-old. It’s not pretty, it’s gross.” A lot of this time went undocumented since it took place in the pre-phone camera era, which is a good thing for the reputations of the celebrities. If these parties happened nowadays, it would be a completely different story (People).

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Mike Tyson Was Banned For Falling Asleep At Movie Night

When there wasn’t a rowdy party happening, Hefner loved hosting movie nights. These would be a lot more PG than the parties. But still, an eclectic mix of celebrities attended, and it was nothing short of amusing. The wild boxer “Iron” Mike Tyson attended one of these movie nights, though Hefner blocked him from attending any future parties. Because Hefner was a huge movie fanatic, hosting one of those parties was like winning the Golden Ticket. When Tyson finally made it to one of these parties, he attended and fell asleep. Because of his lack of enthusiasm and inability to share with others during the night, Hefner banned him from ever coming back. No sleeping allowed, and even Rob Lowe knew how important movie night was. He said, “An invitation to come to the mansion for movie night was a tough ticket to get. You couldn’t buy your way in; you couldn’t use connections or a publicist or any Hollywood lever-pulling. Invitations came directly from Hugh Hefner, and he cast his parties very carefully in those days.” Better be more careful, Tyson! (Radar Online).

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The smoke room John Lennon reportedly burnt artwork in. HGTV.

John Lennon Burned A Cigarette Into A Piece Of Art

Hefner’s art collection was as important to him as his Playboy bunnies. It comes as no surprise that the Beatles also attended one of the wild mansion parties back in the day, but were unappreciative of Hefner’s art collection. During one of their wild parties, John Lennon drank too much alcohol and stubbed his cigarette out on an original Henri Matisse painting. You’d think that this would get Lennon banned from the mansion, considering Tyson was banned for simply falling asleep. But Hefner forgave Lennon and got the painting restored (Radar Online).

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The Annual Midsummer Night’s Dream Parties

Every year in August, Hefner hosted a Midsummer Night’s Dream party. Some celebrities claimed these parties were their favorite ones of the year. The parties started in 1977, and pretty much asked every celebrity to wear their sexiest sleepwear. At a 1979 party, Timothy Leary said, “I think Hefner is one of the four great cultural influences on America.” Where else would you see celebrities in their finest sleepwear? Hefner even expanded the parties to have summertime soirees and NYE pajama parties, all of which were as charismatic as the next (Playboy).

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After One Party, A Llama Was Found Dead

The parties at the Playboy Mansion were out of this world. It’s the only place you’d find exotic animals lurking around the grounds, in Hefner’s very own zoo. After one of their wild parties, a zoo worker sadly discovered a deceased llama. Animal authorities came to the mansion to remove several of the big cats, in fear of their safety. But for some reason, they allowed the peacocks and macaws to stay at the mansion. They never found out what happened to the poor llama. The 80’s and 90’s were a different ballgame entirely. This would never happen nowadays because of how important animal welfare is (Radar Online).

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Rob Lowe Loved The Attention During The Parties

Whenever a handsome celebrity walked into the Playboy Mansion, the women showered them with attention. There was a reason they kept coming back for more, so when Rob Lowe showed up to his first Playboy party, he knew it wasn’t going to be his last. He said, “I felt like a pharaoh or, I suppose, a junior Hugh Hefner. The girls poured me drinks, laughed, flirted, ran their fingers through my hair, and generally seemed to be having as much fun toying with me as they possibly could.” This is just a glimpse into the debauchery that went on in that mansion (Daily Star)

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All Types Of Parties With An Extravagant Backdrop

The parties could go one of two ways. They were either wild and steamy, or sophisticated and relaxed. Terry Keefe attended both versions of these parties. The first party was tame, and she got a tour of the animals. She said, “I remember the Spider Monkey cage being open. The Playmate giving us the tour exclaimed that the cage should be closed and she called for a maintenance person. We were able to enter the cage, where dozens of Spider Monkeys were looking down on us from above. I remember the Zoo also reportedly had a Gibbon but didn’t see it. The grounds of the Mansion had Birds of Paradise freely roaming and they were quite beautiful.” It sounds more like an animal tour than a party at the mansion. But the second party she attended was vastly different. During this party, Naked models dressed in bodypaint walked around taking pictures. A few rock bands and rap acts played, none of which I was familiar with. Hugh Hefner was at this party, accompanied by Playmates who were dressed as prison guards. Hefner wore black and white prison stripes, dressed as their prisoner.” We’re not sure what kind of party we’d rather attend (Fancy Pants Home).

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Inside the Playboy Mansion. San Francisco Interior Designs

Wilder Than Ever

Sarah Robertson was a DJ converted into a Playboy bunny. We’re not sure how that conversion happens, but she claims the parties at the mansion were some of the wildest she’d seen. She said, “Playboy Mansion parties are amazing, wild, and crazy. There were so many famous people there – from Pamela Anderson, Paris Hilton, P Diddy, Jenny McCarthy, Snoop Dogg, Sir Richard Branson, and astronaut Buzz Aldrin.” Partying at the Playboy mansion is one thing, but partying with famous people is another. If only we could go back in time and make it to one of these wild house parties that went down in infamy.

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The Parties Were Full Of Surprise

While Roberston was DJing at the parties, she always said you never knew who would arrive. “It’s always surreal DJing at these parties – you never really know who is going to rock up. I’ll just have someone come up to me behind the decks and say, ‘Paris Hilton has just arrived’, or ‘P Diddy needs the mic’. Those weren’t the only surprises. Because of how big the mansion was, there was no saying what could happen anywhere on the ground. She said, “The grounds are really big, and whether you go to the games room or red room, there’s always a group of people partying in every corner or behind every door you open.” Her career began because of the Playboy mansion parties (LadBible).

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Rihanna And Leonardo DiCaprio’s Kiss

At a wild playboy mansion birthday party in 2015, Rihanna and Leonardo DiCaprio shared a kiss. The celebration was for Nikki Erwin, but it seems like Rihanna and Leonardo were the two stars of the evening. Who knows what happened before and after that kiss, but it was enough to make headlines. The kiss took place during Rihanna’s song. Carly Lauren, a playmate at the mansion, Tweeted “Just saw Leo and Rihanna making out while Pour It Up was playing.” The two were also seen partying together after the mansion celebration (Radar Online).

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Bill Higgins Got A Personal Tour Before A Party

According to the Hollywood Reporter, Bill Higgins showed up at the Playboy Mansion on several occasions. From his report before a party, he got a personal tour of the infamous grounds. He said, “The woman who was escorting us (Bunny? Former Bunny? Non-Bunny?) brought us to the gardens across from the mansion’s front door. These are classic European rose gardens with paths. On one side some small buildings are occasionally occupied. She showed us one sterile small room that had a bed in it but almost nothing else. Then she casually mentioned that in the late 1960s, Bill Cosby had lived in this room for a year. I’m not sure what that tells you about Cosby but it must be something.” The Playboy Mansion holds many secrets behind its hundreds of locked doors (Hollywood Reporter).

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Despite The Parties, The Mansion Was Supposedly Haunted

It wouldn’t be the Playboy Mansion if there weren’t ghosts running around in hot pink sports bras. One of Hefner’s former girlfriends, Holly Madison, once saw an apparition in a hot pink sports bra in the basement. It disappeared into a shallow closet, and she said, “I never saw that woman again in my life.” The toilet would also flush by itself. The wife of the former mansion occupant leaped from the balcony, which explains why it might be haunted (House Digest).

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Painted Clothing

If there’s one place in the world where paint would replace clothes, it would be at the Playboy Mansion. Rita Tennyson, who used to throw parties at the mansion, said, “I saw Paul Stanley there. Each party had a different vibe. Some were just mellow, but the one with Paul Stanley was at night and they were having a celebrity auction. Girls are walking around with painted clothing.” The parties that went down in infamy were certainly not the mellow ones (Fancy Pants Home).

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Paris Hilton Used To Party There

Paris Hilton attended numerous parties at the mansion during the 2000s and early 2010s. But it sounds like she wanted to keep her appearance under wraps, and one time, she even made it to the cover of Playboy without her consent. She even turned down a 7-figure offer from Hefner after the fact. She said, “Hef wanted me to do a Playboy cover,” Hilton recalled. “He kept offering me more and more money, saying I wouldn’t have to be naked, just topless. And then saying, I didn’t have to be topless, just sheer. And then saying I could wear whatever lingerie I wanted. Even when he offered seven figures, I turned it down, because I knew my mom would lose her mind.” If that’s what Hefner wanted her to show to the public eye, there’s no saying what went on during the mansion parties (Insider).

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Pamela Anderson Said The Parties Quickly Turned Wild

Pamela Anderson attended the wild parties at the Playboy mansions. She was quick to dish the dirt at just how wild they got. This included nudity and dirty acts that happened behind closed doors. In an interview, she said, “Everyone was naked in the grotto and the girls were downstairs, and they all went upstairs. I followed them upstairs. I thought, ‘What could be going on up here?’ Seven girls, one at a time with Hef. Then, I stood at the end of the bed watching them and then I realized they were watching me. I thought, ‘This is not a movie. I need to leave.” We can’t imagine the sudden realization you need to leave a Playboy party because of how wild it was, but apparently, it happens, even to the most well-equipped celebrities. She went on to say, “It was a very sexy time. It was all wild, but respectful.” At least it was respectful (The Things).

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Never Kiss And Tell

Even though Pamela Anderson used to party there, she kept a lot of things that happened under wraps. But she did give a hint about the overall vibe of the parties. She once said, While she says “A kiss-and-tell is not my style, the men were elegant, and you wanted to badly get the most charismatic man to notice you. Girls were everywhere, giggling and laughing.” That’s about as much insight into the Playboy parties we’ll ever get (The Things).

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Lewis Hamilton Partied With Snoop Dogg

No famous person was left behind! Even British racing driver Lewis Hamilton was seen partying at the Playboy mansion with rapper Snoop Dogg. After going through a breakup with Nicole Scherzinger, it seemed like Hamilton needed the distraction. There’s no better place in the world to distract yourself than at the Playboy mansion, and there’s no saying what went on there (The Things).

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Trump Brought The Apprentice Team

If you know and love The Apprentice, then you’ll know Trump brought one of the teams to a Playboy mansion party in a 2006 episode. Trump and the winning team headed to the backyard where dozens of Playmates hung around. He said, “It’s hard for me to tell which of these girls are yours, and which ones are mine,” to Hefner. That doesn’t sound like something to brag about, Trump (People).

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Kim Kardashian Loved To Party There

It’s not surprising to learn that Kim Kardashian also loved to party at the Playboy Mansion, and we can only assume what she got up to during her time there. In 2007, she even posed nude for Playboy and regretted it years later. Years later, she said, “I would tell my younger self to ditch some of the outfits. The crazy outfits I can’t believe I wore.” Next time, she needs to think about the future a little bit more, especially when it comes to Playboy. There’s no going back once those photos are out in the world. And based on those photoshoots, we can only imagine what went on during some of those parties (The Sun).

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The Elvis Suite

The secret room at the Playboy Mansion all began because of Elvis Presley and his secret naughty endeavors at the mansion. During one party in the 70s, the rock singer had his own slumber party with eight little bunnies. No one knows what went on behind locked doors, but considering the raunchiness we know does occur at the mansion, it’s safe to assume his actions weren’t PG. Whatever did happen, it impressed Hefner so much that he renamed the room the Elvis Suite. Now, we’re left to our imagination about what happened in the Elvis Suite (Radar Online).

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You Can’t Run From The Blueprints

Jack Nicholson and Warren Beatty were rampant mansion visitors that supposedly had their very own, private tunnels that went from the Playboy mansion to their mansion for easy access. It even granted them a paparazzi-free escape. They got away with it for a while in the 70s, but it wasn’t until 2015 when blueprints confirmed their existence at the mansion, though it was later discovered that the blueprints may have been fabricated. Either way, they were frequent partygoers who had their share of fun at the mansion (Radar Online).

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Quentin Tarantino Made An Appearance

Another famous face often spotted at the Playboy Mansion was Hollywood director Quentin Tarantino. We all know and love him for his incredible movies and creative talent. He apparently chose Holmby Hills for some scenes in Once Upon a Time in Hollywood. The sole purpose of his Playboy mansion visits might have been to scope out inspiration for his movies, though in 2004 he used the mansion for his Kill Bill Vol. 1 release party (The Things).

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Beautiful Friendships Came Out Of The Parties

It would be a shame if nothing good came out of the Playboy parties. We know they were infamous for their readiness, but many friendships formed thanks to the parties. Eve Dawes said, “Obviously, it’s decadent decor and food with free-flowing alcohol but what has stuck with me is the many friendships with girls from across the country that I made. A lot of us still stay in touch. As well as all of the celebrities I’ve seen attend and perform there.” (Fancy Pants Homes).

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Despite The Parties, Hefner Was Still A Creep

Cerridwen Fallingstar, who attended one of the Playboy Mansion parties, said Hefner, amongst several other men, was creepy. She said, “It was a very odd combination of feminists and creeps at that party… Hefner himself, while trying his best to seem sincerely interested in women’s rights (to be infinitely exploited), exuded creepiness, as one might expect.” For someone to throw the types of parties Hefner threw, it’s not surprising to learn he was creepy. Hefner managed to use his creepiness to his advantage, considering the number of bunnies he had wandering the mansion’s premises, working just for him (Fancy Pants Home).

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Disease Breaks Out

It’s not surprising to learn a disease broke out at the mansion. After one party, Legionnaires’ disease ran rampant and affected 123 people, who broke out with a fever and had difficulty breathing. The LA Department of Health traced the disease back to the hot tub at the famed Grotto. This is where they discovered Legionella pneumonia. The notorious grotto was one of the most infamous parts of the Playboy Mansion. This is where a sauna, waterfall, small forest, pond, orchards, and patio were located. The parties went on through the evening and well into the next morning (Radar Online).

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