Although it might’ve taken him a while, Leonardo DiCaprio is now an Oscar-winning actor considered one of the best of his generation. In the 1990s, fresh off the success of The Titanic, DiCaprio was no longer simply the teenager from What’s Eating Gilbert Grape and was ready to enjoy his post-Titanic heartthrob status with considerable enthusiasm.

Stories about DiCaprio’s antics have become the stuff of Hollywood legend, particularly after he joined forces with other up-and-coming actors like Tobey Maguire, Lukas Haas, and Kevin Connolly, forming a sort of band of brothers as they all tried to make it. A competitive edge undoubtedly undercut their friendship, often showing up to the same auditions and taking bets on who’d make it big first.

But DiCaprio was the obvious standout, not least because he’d won the hearts and minds of virtually every teenage girl in America after playing Jack Dawson. Assuming the role of leader, DiCaprio took the group of young actors partying all over New York City, gleefully chasing women, harassing the paparazzi, and pulling off pranks with the same excitement you’d expect of a six-year-old boy, given that the group allegedly took to setting off stink-bombs in fancy bars.

But their interests could swing more adult if the night called for it – like the time they snuck into a Victoria’s Secret event. Their well-documented habit of chasing women meant somewhere along the line; they were dubbed ‘The Pussy Posse’. Crude as it was, it was a pretty accurate label and one that gave them a certain cachet in Hollywood circles. The group breezed through the doors of clubs Mariah Carey had to queue for but seemed most content acting like unsupervised kids and dumping litter off the Brooklyn Promenade.

But just as the friendship was clouded by competition, there were times their antics got carried away, with their film Don’s Plum serving as the most enduring example. Starring, written, and produced by the Posse, DiCaprio and Maguire had a moment of clarity and realised the film was so highly offensive and misogynistic, given that one line from DiCaprio includes: “Stop looking at me like that, I’ll fucking throw a bottle at your face, you goddamn whore”, which is met with laughter in the film.

Now more attuned to the PR machine that was Hollywood, both Maguire and DiCaprio effectively blocked the film’s release. They’d flown too close to the sun, and it was so overtly sexist it was felt it might reflect poorly on how they spoke when nobody was around.

The film’s producer, David Stutman, accused the two actors of abusing their influence to stop Miramax from releasing the film. In the lawsuit, Stutman said: “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.”

Ultimately, a settlement was reached, the compromise being that Don’s Plum could only be released outside of the United States and Canada, much to the delight of the newly PR-conscious actors. Ultimately, the Posse was the perfect reflection of late-90s stardom and all the doors it would open, their boyish camaraderie giving their obsession with women and fame a more charming face.