Celebrity 8 Crazy Playboy Mansion Stories Playboy founder Hugh Hefner, who passed away in September 2017 at the age of 91, entertained Hollywood's most notorious at the Playboy Mansion By Grace Gavilanes Updated on October 12, 2022 05:02 PM Share Tweet Pin Email Trending Videos 01 of 08 There Was a Longstanding Rumor That Jack Nicholson Had a Secret Underground Passageway to the Mansion... Richard Nairin/Michael Ochs Archives/Getty … and so did a few other celebs. After Hugh Hefner purchased the property for $1.1 million in 1971, he was ready to party with his famous friends. It may come as no surprise, considering they were Mansion regulars, but according to blueprints found by Playboy staffers — which were later debunked — underground passageways were built inside the homes of A-listers Jack Nicholson, Warren Beatty, Kirk Douglas and James Caan back in the 1970s. "They both love women," Hefner told PEOPLE of former Mansion fixtures Beatty and Nicholson. 02 of 08 Donald Trump Once Spent Time There Sipa Press/REX/Shutterstock "He was just there, just hanging like Bill Maher," Pauly Shore told radio host Joe Rogan about partying with Donald Trump at the Playboy Mansion. "It was some Easter egg night or day s---, and he was in a suit and talking to girls." 03 of 08 Rihanna and Leonardo DiCaprio Reportedly Made Out at a Party Jesse Grant/Getty They might not have confirmed their relationship status, but rumor has it that the hitmaker and Oscar winner got cozy and shared a kiss during a birthday party celebrating designer Nikki Erwin in 2015. 04 of 08 Trump Escorted 'The Apprentice' Team to the Mansion Mathew Imaging/FilmMagic In a 2006 episode of The Apprentice, Trump treated one of the teams to a party at the Playboy Mansion after winning a challenge. Contestant Surya Yalamanchili recounted the experience for a Politico article, adding that following a fireside chat with Hefner, the winning team — along with Trump — headed to the backyard where they were met with dozens of Playmates. "It's hard for me to tell which of these girls are yours, and which ones are mine," Trump reportedly said to the Playboy mogul. 05 of 08 The Parties Were Just As Wild As You'd Imagine Frank Trapper/Corbis/Getty "It was a very sexy time," Playboy cover model Pamela Anderson told FHM of her time at the Mansion. "It was all wild, but respectful." While she says "a kiss-and-tell is not my style," the star did offer up one tidbit of the overall vibe. "The men were elegant, and you wanted to badly get the most charismatic man to notice you," she said. "Girls were everywhere, giggling and laughing." 06 of 08 Yes, Orgies Happened in the Grotto Ron Galella/WireImage "When I was a Playmate, it was like a library. It was really, really strict. But now when I go there — or a few years ago — it's an orgy," Jenny McCarthy, who was a Playmate over two decades ago, revealed on Watch What Happens Live of the famed grotto (a cave-like structure with a pool) at the Mansion parties. "But it's not sexy. It's, like, David Hasselhoff with an 18-year-old. It's not pretty. It's really gross." 07 of 08 …But Sex Didn't Always Happen at the Mansion Barbi Benton and Hugh Hefner at the Playboy Club. PL Gould/IMAGES/Getty While Hefner's longtime girlfriend Barbie Benton, whom he dated from 1968 to 1976, admitted there were plenty of A-listers either partying or visiting the Mansion, sex wasn't always a given in those moments. "It was not a place that people came necessarily to have sex," she revealed. "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." 08 of 08 Actor Tony Curtis Confided to a Butler About His Relationship With Marilyn Monroe United Artists/Getty "I was by myself in the pantry — the heartbeat of the Mansion — when Tony Curtis came to me and asked if I'd join him for dinner," longtime Playboy Mansion butler Mitch Rosen reminisced in an interview with The Telegraph. "He said, 'Did I ever tell you about the time I worked on Some Like it Hot? [Costar] Jack Lemmon was so angry that Marilyn Monroe and I were sleeping together that he used to throw temper tantrums on the set!'" "I couldn't believe what he was telling me," said Rosen. "I'll cherish that anecdote, and the fact I was a part of the place, for the rest of my life."