True 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 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.

  1. The Name Doubled As A Mission Statement

    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 ‚Äď ahem ‚Äď 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.

  2. Leonardo DiCaprio May Have Propositioned A Reporter For Oral Sex

    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 ‚Äď they all sounded drunk ‚Äď 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.”

  3. 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 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 ‚Äď 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.

  4. Leonardo DiCaprio Pelted People With Grapes And Garbage

    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.”

  5. They Set Off Stink Bombs In Bars

    The members of the Pussy 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.

  6. Harmony Korine Reportedly Stole From Meryl Streep

    Petty theft goes beyond obnoxious youthful exuberance. Pussy 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.'”

  7. Leonardo DiCaprio And Tobey Maguire Made An Offensive Movie, Then Blocked It From Release

    Ranker Videov

    Warning: this clip contains nearly constant profanity.

    In 1998, Leonardo DiCaprio and Tobey 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 ‚Äėleading man‚Äô 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.”

  8. They Were Always Looking For A Fight

    Leonardo 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‚Äôre always ready to start yelling and swinging.”

  9. They Didn’t Tip

    Profiles¬†of the Pussy Posse describe Leonardo DiCaprio as a spendthrift; Ethan Suplee called him “cheap.” One bartender from Spy, a New York City hotspot in the ’90s, said that DiCaprio¬†never tipped. DiCaprio was¬†frank¬†about his spending habits at the time:

    “I’m the cheapest bastard in the world. You never know, I may go bankrupt, or lose my career, or have a Hugh Grant situation.”

  10. They’ve Grown Up A Little

    The Pussy Posse had some wild times in the ’90s. The crew still hangs out, but as the guys have gotten older, they’ve settled down a bit.¬†In 2017, Leonardo DiCaprio,¬†Kevin Connolly, and Lukas Haas went to a play featuring the 10 year-old daughter of their pal Tobey Maguire. Trading in the frosted tips of the 1990s for receding hairlines in the 2010s seems to have forced the group to find more tame activities.

  11. They Adopted A New Name

    They’re still frequently called the “Pussy Posse,” but the group’s¬†members typically claim they never called themselves that and that the name originated from an article about the group. As of 2016, the crew reportedly took to calling themselves the Wolf Pack and began¬†howling all nightwhile out on the town. In case anyone got confused, the gang also took to chanting “Wolf Pack.”