celebrity trivia True Stories From Leonardo DiCaprio's Pussy Posse, The '90s Boy Gang Who Wreaked Havoc In Hollywood  

Hugh Landman
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Leonardo DiCaprio is one of the most accomplished actors of his generation. But before he got Oscar attention or began speaking about environmental issues, he was just a famous young man with a lot of money and a taste for attractive women. Stories about Leonardo DiCaprio in the '90s have become Hollywood legend. He rolled with a crew of like-minded young men in a group with an unapologetically raunchy name: the Pussy Posse. True stories about the Pussy Posse detail their wild times, but they also illustrate how even big-time celebrities can be obnoxious twerps. 

Who was the Pussy Posse? The group included stars like David Blaine, Tobey Maguire, Jay Ferguson, Josh Miller, Ethan Suplee, and Scott Bloom. But the leader was unquestionably DiCaprio. From the mid to late 1990s, DiCaprio took his squad out partying all over New York City. They chased girls, pulled pranks, and clowned the paparazzi. Were they just kids being kids, or were they sexist, law-breaking oafs? Come to your own conclusions after reading these over-the-top tales.

The Name Doubled As A Mission Statement


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The Pussy Posse didn't get its nickname for its members' interest in modern art. The young stars' obsession with partying and girls earned them the title in Hollywood circles in the '90s.

That focus on – ahem – getting to know women apparently continues; in 2016, a story emerged that Leonardo DiCaprio had bet Tobey Maguire that he could sleep with six Victoria's Secret models during the Cannes Film Festival. Reportedly, DiCaprio took an efficient approach by inviting the women to join him in threesomes.

Leonardo DiCaprio May Have Propositioned A Reporter For Oral Sex


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In 1998, Nancy Jo Sales published what would become the definitive look at the Pussy Posse: a piece for New York magazine entitled "Leo, Prince of the City." In the story, she details how she had been attempting to get in touch with Leonardo DiCaprio and came home one night to a bizarre message on her answering machine:

"A group of young guys – they all sounded drunk – were laughing and cutting up in the background. It was kind of strange. The speaker was telling me that if I wanted an interview with him, I'd have to 'make a deal' along the lines of doing something for him that Monica did for Bill. 'Then maybe we'll talk!' he laughed."

They Got Into A Brawl Over Elizabeth Berkley


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Photo: Pathé

At a party for the premiere of The Man in the Iron Mask in 1998, actress Elizabeth Berkley caught the eye of Leonardo DiCaprio and Jay Ferguson. Berkley had a boyfriend, actor Roger Wilson, and she declined their invitation to go to the after-party.

This didn't deter the Pussy Posse, who got Berkley's phone number and relentlessly called her home. Eventually, Wilson got on the phone and told the guys to cut it out – in response, Ferguson unleashed a torrent of profanity. Wilson went to the restaurant where the Posse was dining, and after exchanging a few words, they ended up outside. "Let's go kick his ass," DiCaprio reportedly told his friends. An unidentified member of the Posse ended up punching Wilson in the throat, after which the stars scattered to avoid legal repercussions.

Leonardo DiCaprio Pelted People With Grapes And Garbage


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The Pussy Posse didn't get a reputation for being childish for nothing. In 1998, Leonardo DiCaprio allegedly greeted the paparazzi waiting around outside of his hotel by pelting them with grapes. In another incident, he was reportedly spotted throwing garbage off the Brooklyn Promenade onto cars using the BQE below, "before speeding away in his chauffeur-driven Mercedes."