Can you imagine what it’s like to live hopping from party to party in the company of your best friends?
That’s how life was for Leo DiCaprio during the late 1990s, before he became everyone’s favorite environmental activist. Throughout his youth, DiCaprio truly felt as if he was on top of the world and he carried most of his friends with him to enjoy the view. However, they didn’t realize how many people they were stepping on to feel as entitled as they did.
The name of Leo’s crew was the Pussy Posse, and it was formed during the late nineties. It all started out when Toby Maguire and Leo met on a movie set when they were just kids. Afterwards, the group just grew and grew. Everyone wanted to hang out with the star who would eventually become a worldwide sensation with the release of Titanic. Among the members of the clique were Jay Ferguson, Josh Miller, Ethan Suplee, Kevin Connolly, Scott Bloom, and Justin Herwick. Many of them were actors themselves, but the main role they played was Leo’s cronies.
DiCaprio became the de facto leader of the Pussy Posse after his sudden rise to fame with Titanic. However, instead of arising jealousy among his mates, he made them the entourage that would keep him company in his adventures around the world. He gave his friends the opportunity of living a life of tireless partying, sneaking into Victoria’s Secret Fashion Shows, and going to the most expensive strip clubs. Some of them even came with him to the shooting of Romeo and Juliet in Australia. All that they had to do was to protect each other and keep good company.
However, what the Posse wouldn’t protect was basic human values, nor would they be good company to anyone else in the world. Their careless lifestyle eventually led them to believe they were entitled to insult anyone who wouldn’t grant them their wishes. Their party frenzy eventually made them chase anyone they desired, and when they couldn’t get their fill, there would be consequences.
At the night of the premiere of The Man with the Iron Mask, the Posse was playing around, boasting their rockstar lifestyles in front of everyone around. A girl walking through the door caught the attention of the whole clique. It was Elizabeth Berkley, who had just recently starred on the film Showgirls and was dating Roger Wilson.
Leo and his friends sent Karen Tenzler, an LA publicist, to tell Berkley they were going “crazy about her” and that she should party with the boys. Her boyfriend, however, was not invited to the party. She refused, but by the following day, she was harassed with several phone-calls from Jay Ferguson who was still trying to convince her to go with them. Wilson tried to intervene, telling the Posse that even though they thought they owned the town, they didn’t. Ferguson answered through homophobic slurs and dared Wilson to face them. Just a few nights afterwards, Wilson stood up to the Posse at the Asia de Cuba restaurant, but it only ended in him getting an injured larynx.
The Posse wouldn’t take anything from anyone who stopped them from getting everything they wanted in the world. This ended up in them adopting a toxic macho attitude, taking for granted that any girl they wanted would agree to party with them just because they were the most popular rich boys in the block.
The uncouth and reckless behaviors of the Posse got immortalized in a film written, starred, and produced by themselves. The movie Don’s Plum (1995) portrays a group of LA youths meeting at a local diner to discuss their life experiences, and in a sense, it portrayed the true dynamics and world perceptions of the Posse. Unsurprisingly, some of its dialogues —which were mostly achieved through improvisation— are just plain misogynistic, which makes it feel like that was the way the Posse truly acted and talked. Because of this, chaos stirred around the distribution of the film, and both Leo and Toby Maguire sued the director R.D. Robb because neither of the actors were happy with the image of them that the film portrayed. The issue was eventually settled out of court, but the movie never got to screen in the USA or Canada because it would have been too detrimental for Leo and Maguire’s careers.
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