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

Updated August 13, 2019 1.8m views11 items

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? 

  • 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

    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.'

  • DiCaprio And Maguire Made An Offensive Movie, Then Blocked It From Release

    Video: YouTube

    In 1998, DiCaprio and Maguire made a movie called Don's Plum that never made it to theaters. It was written, directed, and produced by the Posse, but apparently, it was so awful that DiCaprio and Maguire decided to block its release. In a suit against the actors, producer David Stutman said they used their connections with Miramax to get the potentially damaging film withheld from theaters:

    Maguire and his manager had determined that, in the Film, Maguire did not come off as strong a 'leading man' as DiCaprio and that some of the improvisational comments Maguire had made during the Film revealed personal experiences or tendencies that would undermine the public image he and his manager were trying to project.

    In 2019, the New York Post produced a three part docu-series about the project called The Curse of Don's Plum. The docu-series unpacks the failure that was Don's Plum and revisits the minds behind the film through interviews with the director, producers, and writers. 

  • They Were Always Looking For A Fight

    Photo: Alan Light / Wikimedia Commons / CC BY 2.0

    DiCaprio and his boys got into a lot of mischief in their time, and often that mischief led to trouble. Luckily, the Posse wasn't afraid to act macho. DiCaprio's friends apparently relished fights, as one paparazzo remembered: "They get off on protecting him [...] They're always ready to start yelling and swinging."