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

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 that Hollywood circles at the time branded with an unapologetically raunchy name. True stories about the Posse not only detail their wild times, but they also illustrate how even big-time celebrities can be obnoxious twerps. 

Who was in the Posse? The group allegedly 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. They even endeavored to produce an independent film called Don's Plum. The film is all about their misogynistic misadventures but was so terrible that Maguire and DiCaprio blocked it from release and it was ultimately banned in the US. In 2019, the New York Post produced a three part mini-series called The Curse of Don's Plum that examines what went wrong with the project. 

The question that remains is, was the Posse just a group of kids being kids, or were they sexist, law-breaking oafs? 


  • The Name Doubled As A Mission Statement

    The Name Doubled As A Mission Statement
    Photo: Siebbi / Wikimedia Commons / CC BY 3.0

    The Posse didn't receive 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 allegedly continued past the group's '90s heyday. Later, a story emerged that 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.

  • DiCaprio May Have Propositioned A Reporter

    DiCaprio May Have Propositioned A Reporter
    Photo: Georges Biard / Wikimedia Commons / CC-BY-SA 3.0

    In 1998, Nancy Jo Sales published what would become the definitive look at the Posse: a piece for New York Magazine titled "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

    At a party for the premiere of The Man in the Iron Mask in 1998, actress Elizabeth Berkley caught the eye of 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 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 [butt]," DiCaprio reportedly told his friends. According to the NY Mag feature, an unidentified member of the Posse ended up punching Wilson in the throat, after which the stars scattered to avoid legal repercussions.

  • DiCaprio Allegedly Pelted People With Grapes And Garbage

    The 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, "before speeding away in his chauffeur-driven Mercedes."

  • They Set Off Stink Bombs In Bars

    They Set Off Stink Bombs In Bars
    Photo: Igormattio / Pixabay / Pixabay License

    The members of the Posse were all legally adults when they were rampaging through New York and terrorizing unsuspecting citizens, but they acted more like children. For instance, the band of bros was known to go to a popular New York City night spot, Sky Bar, and unleash stink bombs in the midst of the crowd.

  • Harmony Korine Reportedly Got Caught Stealing From Meryl Streep By David Letterman

    Harmony Korine Reportedly Got Caught Stealing From Meryl Streep By David Letterman
    Photo: Gdcgraphics / Wikimedia Commons / CC BY 2.0

    Petty theft goes beyond obnoxious youthful exuberance. Posse member and director Harmony Korine apparently dabbled on the wrong side of the law in 1998, and his attempted thievery got him banned from The Late Show with David Letterman. Korine was set to appear on an episode with Meryl Streep, but Letterman caught him in a compromising situation:

    I went upstairs to greet Meryl Streep and welcome her to the show, and I knock on the door... and she was not in there. And I looked around, and she was not in there, and I found Harmony going through her purse. True story. And so I said, 'That's it, put her things back in her bag and then get out.'