Both Leonardo DiCaprio and Tobey Maguire are renowned for being some of the biggest elites in the entire entertainment industry. For ones who started their career as heartthrobs, the pair have managed to keep their reputation still and continue to reside in fans’ hearts even after being almost fifty years old, all the while leading thriving decades-old careers.

Tobey Maguire and Leonardo DiCaprio in The Great Gatsby

But these thriving careers and reputations of theirs were almost ruined during their very start. All because of their notoriety and roguishness as newly made Hollywood heartthrobs, Leonardo DiCaprio and Tobey Maguire almost ruined their careers after their group got dubbed by critics as the “P—y Posse”.

Leonardo DiCaprio and Tobey Maguire almost jeopardized their reputations in the ’90s

Leonardo DiCaprio and Tobey Maguire in The Great Gatsby
Back in the mid-1990s in Hollywood, multiple young aspiring actors often ran into each other during auditions. While others usually ended up becoming rivals due to the competition, the same wasn’t the case with Leonardo DiCaprio, Tobey Maguire, and their star-studded band of notorious youngsters which included Lukas Haas, Kevin Connolly, and Jay Ferguson for a few to count.

Instead of competing against each other for the roles in a way that could induce bad blood between them, these youngsters decided to become friends with each other, with major credit to Leonardo DiCaprio. Even though “making it” was their aim and they were competitive too, considering how they were aspiring actors; the youthful boyband also believed in having fun along the way.

According to what an anonymous actor told New York Magazine‘s Nancy Jo Sales, which later made its way to get covered in her Leo, Prince of the City profile: “A little competition rose up between them. They were always betting on who would blow up first.” But it wasn’t the competition that almost put their careers on the line, but rather their desire to have “fun along the way.”

As can be expected from almost any and every group of young, good-looking guys in their ending teens or early twenties, this group was no different: They did anything and everything to have “fun”, from nights outs spent sneaking into Victoria’s Secrets events to spur-of-the-moment trips to Vegas. Yet, what actually landed them into trouble the most was that they were always chasing girls.

In the same Leo, Prince of the City profile, Sales mentioned the same about how these youngsters were often seen chasing after girls, as a photographer once reported to her:

“They’re all about seeing the girls.”

Because of this one trait, this young, infamous band of mischievous misfits came in the eyes of the media and the critics a little too often, most specifically for their partying and their roles. This eventually ended up with them earning a title that could pretty easily jeopardize their reputations and land them in trouble: “The P—y Posse.”

But even as this group consisting of mainly Leonardo DiCaprio and Tobey Maguire in the lead continued to be renowned as the P—y Posse even now, somehow — perhaps because of the leading roles they scored that launched them to the top — they managed to both save their reputation and continue to lead thriving careers ahead.

The P—y Posse still exists, but not in the same way they did in the ’90s

For those who are just hearing this story, the P—y Posse still exists and meets up every now and then to remind the world (and themselves) that they’re still as good friends as they used to be before. Yet, it’s not the same as it was back in the 1990s, with their roguish charms gone and most of them having already moved on to start their own families.

Tobey Maguire is hitched to Jennifer Meyer and shares a daughter with her, Kevin Connoly is married to Zulay Henao with one kid, and Jay Ferguson has tied the knot with Lorean Ruiz and shares 3 children with her. Even Leonardo DiCaprio has seemingly grown up, what with the millions he spends on environmental concerns each year, even though he is, still, as interested in young women as he was back then.

Yes, the P—y Posse still exist and hang out together, but they’re not the same as the youngsters in their late teens or early 20s who liked to steal other guys’ girlfriends. No, the P—y Posse has grown up, and very much so.